September First Friday
Shops stay open late, many run sales, and street parking is free after five. The Rescue Dogs Band plays the Historic Courthouse and The Richard Brothers Band plays Gay Street.
28 things on this weekend, 369 on the calendar.
Shops stay open late, many run sales, and street parking is free after five. The Rescue Dogs Band plays the Historic Courthouse and The Richard Brothers Band plays Gay Street.
Four blocks of Gay Street close to cars so restaurants push tables into the road. Walk down the middle of the street, eat outside, and browse the shops on either side.
The resident artists open the studio on First Friday. Abstract and realist work, fabric art, stained glass, with new pieces rotating in. Snacks and drinks, and the artists are there to talk.
Bring your own records and they spin them. Six to ten every Friday at the West Market Street bar, free, and the queue is whoever turns up with a sleeve.
Two hours for families at the Gay Street diner on Friday evenings, six to eight, through the end of September.
Youth Day at Vonnie Gros Field, so the Rams build the night around kids who play. Friday 7 p.m. start against Assumption University.
The Philly Keys take requests for three hours on First Friday, all sing along and crowd noise with Brian Aglira leading. Tables sell out every month, so reserve ahead.
First Friday of September on the Slow Hand stage. Downtown is already busy that night, so get there before nine.
Friday karaoke at the Market Street bottle shop and bar, nine o'clock, free. It runs Saturdays at the same hour too.
A late Friday set at the East Market Street bar, starting at 9:30. Covers band, small stage, and the room gets loud fast.
Ten p.m. Friday karaoke in the basement bar on West Gay Street, free to walk in. It goes late, and the list gets long once the Gay Street crowd spills over.
Four blocks of Gay Street close to cars so restaurants push tables into the road. Walk down the middle of the street, eat outside, and browse the shops on either side.
Nine to six on the Saturday of Labor Day weekend at the working farm on Thornbury Road, with the CSA pickup running alongside the market stalls. Cash and card both fine.
A Saturday morning pulling invasives and tending meadow on the 571 acres along the East Branch. Two and a half hours, tools provided, no experience wanted.
The West Chester Growers Market runs Saturday, October 17, 2026, from 9 a.m. to 1 p.m. at the corner of Church and Chestnut Streets in the borough. That is its regular slot every Saturday from May through December; from January through April it shifts to the first, third and fifth Saturdays, 10 a.m. to noon. For parking, the market's site sends you to downtown West Chester's own parking page. This is a producer-only market and the bylaws mean it: vendors sell only what they grow or produce themselves, and anyone who just resells is turned away at the application stage. The weekly roster averages 28 producers from the surrounding region. Expect seasonal fruits and vegetables alongside meats, cheese, local honey, breads, pastries, roasted coffee, local wines and spirits, hard ciders, fresh flowers, bedding plants and prepared foods. The member list runs from Big Sky Bread and Tally Ho Coffee to Society of Bacon, Conebella Farm, Vera Pasta and North Star Orchard, with rotating guests such as Hank's Cinnamon Buns and Rosie's Kettle Corn filling in around them. A Community Tent hosts non-profits and musicians who apply for a spot. The market opened on this same corner in July 1995 with 10 farmers, and its own pitch is a plain one: come and shake the hand that feeds you. Saturday's window is 9 a.m. to 1 p.m., and the shorter winter hours do not start until January.
The West Chester Walking Club picks a different downtown spot each week and sets off at 9:30. Easy pace, no sign up, and some weeks the group ends up in a shop or a cafe.
An indoor maker market in a Carter Drive warehouse, open three hours on Saturday mornings. Bakers, hot sauce people, prepared food, coffee. Same lot as Levante if you want to make a morning of it.
The same disease-history walk through West Chester, run late morning on Saturdays. Ninety minutes on foot, sixteen dollars, starting from the Chester County History Center on North High Street.
Two hours of real field method and excavation technique, minus the Indiana Jones part. Hands on, at the helicopter museum, and yes there is actual digging.
An hour building an eight to ten inch glass terrarium with four plants and decorative bits to arrange. Bring your own bottle, and give yourself fifteen minutes to park.
AM Radio replays the 1960s and early-70s hit parade at Uptown Knauer on Saturday, September 5, curtain at 7:30. Buy through the theater's own site; Uptown warns that resale listings are the only fakes in the building.
Salsa, bachata and merengue on the floor from eight, with a lesson early on for anyone who needs it. Off West Town Road, parking on site.
Saturday night set at the Church Street cocktail bar. Kitchen is open late if the plan started with drinks and drifted.
The Saturday half of the Bier and Loathing karaoke weekend, nine o'clock on West Market Street, free to sing. Same setup as the Friday night, usually a fuller room by then.
Four blocks of Gay Street close to cars so restaurants push tables into the road. Walk down the middle of the street, eat outside, and browse the shops on either side.
Take a two-hour scenic train ride from West Chester to Glen Mills aboard the historic West Chester Railroad, a restored line dating back to 1831. Bring a picnic lunch to enjoy at the preserved 1880s Glen Mills station, and explore nearby Red Brick Winery. A relaxing way to spend a Labor Day Sunday afternoon with the family. Adults $25, children $20, family pack $67.50. Departs at noon.
Labor Day weekend bingo in the taproom. Two to four on Sunday, same as every week.
Sunday night karaoke at the Gay Street pub, starting at ten and free to walk into. It runs every week into January.
Labor Day, and the street stays closed. Four blocks of Gay Street without cars, restaurant tables out in the road, and the shops on either side open for the holiday.
Taproom doors open on the holiday from noon to five, so the long weekend has somewhere to land that is not your own back yard.
Monday night poker at Saloon 151. Seven thirty start, downstairs bar, no buy-in listed.
Labor Day Monday quizzo at Kildare's, nine o'clock. Free, walk in with a team or make one at the bar.
Monday music bingo at Barnaby's on High Street. Ten o'clock, free, and it fills once term is back in session.
Tape off a pattern, spray a mason jar, take home a container for a shelf somewhere. Happens outside, so the weather decides. Registration required.
Free drop in yoga by the historic water tower at Oakbourne Park, Tuesday evenings into fall. All levels, ages sixteen and up. Bring a mat and something comfortable.
September edition of the Uptown open jam. Players sign up, DJ HA keeps it moving, and the room turns over every few numbers.
Weekly Tuesday quizzo downtown. Eight o'clock at Saloon 151, free, and busier now that the term has started.
Weekly Tuesday karaoke with a real stage and a fifty dollar gift card for the night's best. Drink specials start two hours early.
Tuesday karaoke on Walnut Street, nine o'clock. Free, and a smaller room than the High Street options.
Tuesday karaoke at Barnaby's on High Street. Ten o'clock start, free, and one of three karaoke rooms downtown that night.
Downtown shops and restaurants hiring for the semester, all in one room. Students check in at align.Space on West Market and leave with a map of who is looking. Rain date September 10.
A ninety-minute walk through West Chester built around the epidemics that shaped the borough, on a different route from last year's version. Wednesday evenings from the History Center on North High Street.
Wednesday trivia at Levante. Bring three or four people, order a flight, and argue about the geography round.
Weekly quizzo on High Street. Seven thirty Wednesday, free entry, teams welcome at any size.
Weekly Wednesday trivia on Gay Street. Eight o'clock start, no cover, teams form at the bar.
Weekly late-night pong at Kildare's on Gay Street. Free to play and busier once the university term is running.
Wednesday karaoke at Ryan's on West Gay, ten o'clock, no cover. The far end of the block from Kildare's, if you want to compare.
A hybrid book talk on Richard Bell's history of the American Revolution, run by the Chester County History Center. Ten in the morning, which makes it a coffee-and-argument sort of hour.
An hour on figuring out what you actually want next, run as a guided workshop in the community room. In person, free.
The taproom's monthly dog-friendly stretch, five to seven on a Thursday. Bring the dog, get a beer, let somebody else's retriever handle the socializing.
Two shows open the same night: Hue of Memories II, curated by Jie Deng, in the Allinson Gallery, and Plant Portraits from the Philadelphia Society of Botanical Illustrators in the Huston.
Seven o'clock Thursday trivia at Station 142 on East Market, an hour earlier than the Gay Street rounds, so you can play here and still make one of those.
The festival's big-room Thursday show, five comics including Samantha Ruddy. Starts half an hour after the Turks Head set, so you can only pick one.
Thursday quizzo at eight, free to play. One of four trivia nights running within three blocks that night, so pick your crowd.
Two hours of music trivia on Thursdays, eight to ten, no cover. Get there early if you want a table for more than four.
Karaoke takes the room over right after the trivia round finishes, ten p.m. every Thursday on West Gay Street. Free to walk in, free to sing, and it runs into January.
Four blocks of Gay Street close to cars so restaurants push tables into the road. Walk down the middle of the street, eat outside, and browse the shops on either side.
Reenactors ride the vintage cars to Glen Mills in uniforms spanning several wars, with field gear and firearms out on the tables. Two departures, noon and 2:30. Thirty dollars for adults.
Five hours of Grateful Dead music on the Brandywine Red Clay grounds off Unionville Wawaset Road. Bring a chair, plan for the field, and expect it to run until ten.
Bring your own records and they spin them. Six to ten every Friday at the West Market Street bar, free, and the queue is whoever turns up with a sleeve.
Two hours for families at the Gay Street diner on Friday evenings, six to eight, through the end of September.
Premiere of an independent superhero feature in the History Center on North High Street. Doors at seven, three hours booked.
Revival Productions stages the 1950s rock-and-roll sendup Bye Bye Birdie at Uptown Knauer, ten performances from September 11 to 27. Opening night tacks on a dress-up cocktail party with an open bar before the 7:30 show, and the September 24 performance is open-captioned.
The festival's Friday night headline set, tucked into a studio off Prescott Alley behind Market Street. Eight until half nine, and the room holds a fraction of what a club would.
Six comics in a hair salon after closing, which is exactly the kind of room this festival keeps finding. Runs against the Windish headliner.
Friday karaoke at the Market Street bottle shop and bar, nine o'clock, free. It runs Saturdays at the same hour too.
Ten p.m. Friday karaoke in the basement bar on West Gay Street, free to walk in. It goes late, and the list gets long once the Gay Street crowd spills over.
Four blocks of Gay Street close to cars so restaurants push tables into the road. Walk down the middle of the street, eat outside, and browse the shops on either side.
The farm switches to fall mode for the weekend: hayrides, the corn maze, apple picking and cider donuts out of the bakery. Opening weekend of a run that goes to November.
Half an hour of talking, an hour of everybody reading their own book, half an hour of talking about it. The September meetup lands in Carlino's coffee shop and bakery cafe.
A morning on Pennsylvania German fraktur birds, run with the PA Guild of Craftsmen. Three hours, materials at the table, no prior drawing required.
Forty booths run by kids aged five to fourteen who built the product, the brand and the pitch. Three hours at Jack's Corner, and yes, you are meant to buy things.
Gay Street is already closed to cars for the market, so the mats go down on the pavement near the post office. Five dollars, one hour, all levels welcome.
The West Chester Growers Market runs Saturday, October 17, 2026, from 9 a.m. to 1 p.m. at the corner of Church and Chestnut Streets in the borough. That is its regular slot every Saturday from May through December; from January through April it shifts to the first, third and fifth Saturdays, 10 a.m. to noon. For parking, the market's site sends you to downtown West Chester's own parking page. This is a producer-only market and the bylaws mean it: vendors sell only what they grow or produce themselves, and anyone who just resells is turned away at the application stage. The weekly roster averages 28 producers from the surrounding region. Expect seasonal fruits and vegetables alongside meats, cheese, local honey, breads, pastries, roasted coffee, local wines and spirits, hard ciders, fresh flowers, bedding plants and prepared foods. The member list runs from Big Sky Bread and Tally Ho Coffee to Society of Bacon, Conebella Farm, Vera Pasta and North Star Orchard, with rotating guests such as Hank's Cinnamon Buns and Rosie's Kettle Corn filling in around them. A Community Tent hosts non-profits and musicians who apply for a spot. The market opened on this same corner in July 1995 with 10 farmers, and its own pitch is a plain one: come and shake the hand that feeds you. Saturday's window is 9 a.m. to 1 p.m., and the shorter winter hours do not start until January.
Third year of the Community Volunteers in Medicine run. Nine a.m. start at West Goshen Community Park, with a family walk for anyone not chasing a time.
The West Chester Walking Club picks a different downtown spot each week and sets off at 9:30. Easy pace, no sign up, and some weeks the group ends up in a shop or a cafe.
A self-guided walk through private gardens in the northwest corner of the borough, map emailed the week before. There is a plant sale at the school. Twenty five dollars, rain or shine.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen in the library community room. Beginners get taught, regulars get a game. No registration, just turn up.
An indoor maker market in a Carter Drive warehouse, open three hours on Saturday mornings. Bakers, hot sauce people, prepared food, coffee. Same lot as Levante if you want to make a morning of it.
The same disease-history walk through West Chester, run late morning on Saturdays. Ninety minutes on foot, sixteen dollars, starting from the Chester County History Center on North High Street.
Pony rides and face painting for the kids, a doughnut eating contest and an apple peeling contest for everyone else, plus a dog costume contest, food trucks and a band. Free.
New Eagles clothing drop, a Philly pretzel and four hours of people arguing about the season on West Gay Street.
Two hours of real field method and excavation technique, minus the Indiana Jones part. Hands on, at the helicopter museum, and yes there is actual digging.
Six hours of bingo in the church hall with the Rustin boys soccer program taking the proceeds. Doors at three, last game at nine, kitchen open the whole way through.
Three and a half hours on the roof of the Chestnut Street parking garage looking out over downtown. Proceeds go to the Downtown West Chester Foundation.
An hour building an eight to ten inch glass terrarium with four plants and decorative bits to arrange. Bring your own bottle, and give yourself fifteen minutes to park.
Division II football under the lights against Indiana University of Pennsylvania, the first home date of the season for the Golden Rams. Tickets are sold online ahead of time through wcupatix.
Improv troupe Better Than Bacon builds a whole show out of audience shout-outs at Uptown on Saturday, September 12 at 7:30. They play this stage often enough that the crowd tends to know the drill.
Shane O'Connor hosts comics competing for a date while the audience decides. Closing night of the festival at Turks Head.
Final showcase of the weekend with Cassandra Kyriazis, Kyle Zeigler, Lydia Orme, Pat George, and Matthew Liam. Late slot in the gallery.
The Saturday half of the Bier and Loathing karaoke weekend, nine o'clock on West Market Street, free to sing. Same setup as the Friday night, usually a fuller room by then.
Four blocks of Gay Street close to cars so restaurants push tables into the road. Walk down the middle of the street, eat outside, and browse the shops on either side.
The farm switches to fall mode for the weekend: hayrides, the corn maze, apple picking and cider donuts out of the bakery. Runs weekends into November.
Twenty-five years on. A 5K, a rucked 5K and a one-mile walk named for Sergeant Sambuco and Corporal O'Connor, starting at Rustin High School. Runners, ruckers and walkers all welcome.
Two hour round trip down the Chester Creek valley to Glen Mills with a long layover at the 1880s station. Pack lunch for the picnic grove or walk over to Red Brick Winery.
A two-hour vintage train run down to Glen Mills with living-history military encampments waiting at the other end. Tickets start at thirty dollars and the noon departure is the only one.
Sunday bingo at the West Chester taproom. Afternoon slot, two hours, no sign-up needed.
Sunday night karaoke at the Gay Street pub, starting at ten and free to walk into. It runs every week into January.
Two and a half quiet hours of the treehouse park with the adventure activities shut and nobody over five in the way. Twelve dollars a head, tickets bought ahead, and it runs daily from here.
Westtown Township session for people new to the game or shaky on the rules, on the Oakbourne courts. Runs Mondays through October 5 with Labor Day off. Register through Just Tennis before you show up.
An hour on the grass under the old Oakbourne water tower, kids and grown-ups on mats together. Ten dollars per child, adults free. Bring your own mat and pay cash or Venmo at the park.
Seven dollar films on select Mondays at seven, in the theater on North High Street. The lineup runs all ages and changes month to month.
Woody and Buzz on the Uptown screen for Monday movie night. Cheap tickets, short runtime, easy call for a school-night outing with kids.
The fall storytime session for babies up to a year, five Tuesdays in the community room. Registration opened in early September and the sessions fill.
Five weeks of Tuesday storytime for twelve to twenty four month olds in the community room, part of the library's fall session that starts mid September.
Carve your own mini stamps, ink them, then print your design onto a small tote bag you keep. An hour, registration required.
Free drop in yoga by the historic water tower at Oakbourne Park, Tuesday evenings into fall. All levels, ages sixteen and up. Bring a mat and something comfortable.
Tuesday quizzo at Saloon 151, eight o'clock. Free to enter and the rounds run about two hours.
Tuesday night karaoke on Market Street. Win the week and you are in the running for the grand prize round later on.
The Wednesday half of toddler storytime for twelve to twenty four month olds. Five weeks in the community room, starting the third week of September.
The adult book group takes on the month's pick at one in the afternoon. The title list lives on the library blog, and they ask you to register so they can count chairs.
A ninety minute cooking class from the food bank's Eat Fresh programme, built around Pennsylvania grown produce and the dishes students actually cook at home.
Rose Lang of Resilience with Rose runs an hour on getting through a big transition, working out what you want next and taking the first step toward it.
A ninety-minute walk through West Chester built around the epidemics that shaped the borough, on a different route from last year's version. Wednesday evenings from the History Center on North High Street.
The Fund for Women and Girls screens excerpts from the Moms First documentary, then opens the floor to local groups working on caregiving. Free, with seats reserved ahead at thefundcc.org.
Weekly general trivia in the taproom. Six thirty to eight thirty, no cover, and Levante's own beer on all twenty-odd lines.
Mid-September open mic at Station 142. Four hours of rotating players on a stage with proper sound, sign-up through the venue site.
Standing Wednesday quizzo at Barnaby's. Seven thirty, free, 15 S High Street.
Wednesday music bingo downtown. Eight o'clock at Saloon 151, free, and the song list skews toward whatever the room knows.
Mid-September Wednesday trivia at Side Bar. Standing weekly game in the middle of the Gay Street block.
Wednesday karaoke at Ryan's on West Gay, ten o'clock, no cover. The far end of the block from Kildare's, if you want to compare.
Wednesday pong at the Gay Street pub, ten o'clock. No cover, sign-up at the bar.
The Thursday sitting of storytime for two and three year olds, five weeks in the community room. Same programme as Wednesday, different day.
Storytime for three to five year olds, five Thursdays in the community room. The last stop before kindergarten, and the loudest of the fall sessions.
Conference field hockey at four on a Thursday against Millersville. Vonnie Gros Field is named for the coach who built the program, and the sideline is free.
Two hours of modern board games for adults in the community room, every other Thursday. Games are there, you just need to turn up.
September's veterans hour at Artillery's West Chester taproom. One hour, same time every month, open to anyone who served.
Seven o'clock Thursday trivia at Station 142 on East Market, an hour earlier than the Gay Street rounds, so you can play here and still make one of those.
Free monthly hangout for people with unfinished projects. Bring yours and something to drink, or use the supplies they keep on hand. Third Thursday, seven to nine.
Philly trombonist and singer Hailey Brinnel brings her quintet to Uptown's jazz cocktail hour on Thursday, September 17, swinging through a set of 1970s songs. Downbeat is 7:30, drinks come first.
Two hours of music trivia on Thursdays, eight to ten, no cover. Get there early if you want a table for more than four.
Thursday quizzo at eight, free to play. One of four trivia nights running within three blocks that night, so pick your crowd.
Karaoke takes the room over right after the trivia round finishes, ten p.m. every Thursday on West Gay Street. Free to walk in, free to sing, and it runs into January.
Four blocks of Gay Street close to cars so restaurants push tables into the road. Walk down the middle of the street, eat outside, and browse the shops on either side.
Bring your own records and they spin them. Six to ten every Friday at the West Market Street bar, free, and the queue is whoever turns up with a sleeve.
Two hours for families at the Gay Street diner on Friday evenings, six to eight, through the end of September.
Friday karaoke at the Market Street bottle shop and bar, nine o'clock, free. It runs Saturdays at the same hour too.
Ten p.m. Friday karaoke in the basement bar on West Gay Street, free to walk in. It goes late, and the list gets long once the Gay Street crowd spills over.
Hands on STEM stations, aircraft on display, and a panel of people working in aviation and aerospace on how they got there. The ticket includes museum admission, free for members.
The farm switches to fall mode for the weekend: hayrides, the corn maze, apple picking and cider donuts out of the bakery. Runs weekends into November.
Four blocks of Gay Street close to cars so restaurants push tables into the road. Walk down the middle of the street, eat outside, and browse the shops on either side.
Lithium, lithium-ion, NiMH and nickel-cadmium accepted, loose and taped, up to twenty-five pounds. No alkaline AAs, no car batteries, nothing swollen or leaking. Runs alongside the township yard sale.
The West Chester Growers Market runs Saturday, October 17, 2026, from 9 a.m. to 1 p.m. at the corner of Church and Chestnut Streets in the borough. That is its regular slot every Saturday from May through December; from January through April it shifts to the first, third and fifth Saturdays, 10 a.m. to noon. For parking, the market's site sends you to downtown West Chester's own parking page. This is a producer-only market and the bylaws mean it: vendors sell only what they grow or produce themselves, and anyone who just resells is turned away at the application stage. The weekly roster averages 28 producers from the surrounding region. Expect seasonal fruits and vegetables alongside meats, cheese, local honey, breads, pastries, roasted coffee, local wines and spirits, hard ciders, fresh flowers, bedding plants and prepared foods. The member list runs from Big Sky Bread and Tally Ho Coffee to Society of Bacon, Conebella Farm, Vera Pasta and North Star Orchard, with rotating guests such as Hank's Cinnamon Buns and Rosie's Kettle Corn filling in around them. A Community Tent hosts non-profits and musicians who apply for a spot. The market opened on this same corner in July 1995 with 10 farmers, and its own pitch is a plain one: come and shake the hand that feeds you. Saturday's window is 9 a.m. to 1 p.m., and the shorter winter hours do not start until January.
Anything with a plug, dropped at the township building between nine and noon. Pre-registering keeps the car line moving, though the township says it is not required. Read the flyer before you load the trunk.
Driveways across the township plus tables at the municipal building, all in one three-hour window. Sellers register and pay ahead of time, buyers just drive the map. Nine to noon.
The West Chester Walking Club picks a different downtown spot each week and sets off at 9:30. Easy pace, no sign up, and some weeks the group ends up in a shop or a cafe.
The Historical Commission walks through the interior of the Westtown Inn, also known as the Darlington Inn, using rarely seen photographs and a digital scan of the building.
An indoor maker market in a Carter Drive warehouse, open three hours on Saturday mornings. Bakers, hot sauce people, prepared food, coffee. Same lot as Levante if you want to make a morning of it.
Around 150 artists hang work along the park trails for a day, with live music, food trucks, a teen artist competition and a beer and wine garden. Fifth year running.
Twice-daily skirmish reenactments of the Battle of Brandywine, encampments, blacksmithing and wool dying, modern artisans selling, plus beer and wine. A colonial tavern night with cannon fire starts at six.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen in the library community room. Beginners get taught, regulars get a game. No registration, just turn up.
Ten hours of Oktoberfest at the Carter Drive taproom, one of the brewery's own annual traditions. Lederhosen optional. There is a Prost package you can order ahead if you want the glassware.
The same disease-history walk through West Chester, run late morning on Saturdays. Ninety minutes on foot, sixteen dollars, starting from the Chester County History Center on North High Street.
Saturday afternoon conference soccer against Bloomsburg, kickoff at 2:30. The women played at noon, so the whole afternoon is covered on one campus.
An hour building an eight to ten inch glass terrarium with four plants and decorative bits to arrange. Bring your own bottle, and give yourself fifteen minutes to park.
The Saturday half of the Bier and Loathing karaoke weekend, nine o'clock on West Market Street, free to sing. Same setup as the Friday night, usually a fuller room by then.
The farm switches to fall mode for the weekend: hayrides, the corn maze, apple picking and cider donuts out of the bakery. Runs weekends into November.
Four blocks of Gay Street close to cars so restaurants push tables into the road. Walk down the middle of the street, eat outside, and browse the shops on either side.
The 45th year of downtown closing Gay and Market Streets so 50-plus restaurants and food trucks can feed the crowd. Sunday noon to 5:30, with three stages of bands and a rain date the following Sunday.
Two hour round trip down the Chester Creek valley to Glen Mills with a long layover at the 1880s station. Pack lunch for the picnic grove or walk over to Red Brick Winery.
Sunday bingo on the standing weekly schedule at Levante. Two to four in the taproom.
The harder soldering session, open only to teens and tweens who did one of Mr. Hildwine's earlier classes. Kit count caps the room, so there is usually a waitlist.
Free drop in yoga by the historic water tower at Oakbourne Park, Tuesday evenings into fall. All levels, ages sixteen and up. Bring a mat and something comfortable.
Standing Tuesday quizzo at the west end of Gay Street. Eight o'clock, free, no sign-up needed.
Tuesday karaoke, drink specials from eight and microphone from ten. One of the few weeknight rooms in the borough that stays busy past midnight.
Standing Tuesday karaoke at Bierhaul. Nine o'clock, free, 15 N Walnut Street.
Standing Tuesday karaoke at Barnaby's. Ten o'clock, free, 15 S High Street.
Wednesday trivia at the Carter Drive taproom, running on the standing weekly schedule. Six thirty start.
Wednesday night quizzo downtown at Barnaby's. Seven thirty start, no entry fee.
Wednesday night trivia at Side Bar, eight o'clock. Walk in with three friends and you have a team.
Standing Wednesday pong night at Kildare's. Ten o'clock start, free entry, downtown location you can walk home from.
Uptown's Laugh Lounge stand-up night lands on Thursday, September 24 at 7:30. It shares the building with the Bye Bye Birdie run that week, so the High Street block will be moving.
Four blocks of Gay Street close to cars so restaurants push tables into the road. Walk down the middle of the street, eat outside, and browse the shops on either side.
Four blocks of Gay Street close to cars so restaurants push tables into the road. Walk down the middle of the street, eat outside, and browse the shops on either side.
The farm switches to fall mode for the weekend: hayrides, the corn maze, apple picking and cider donuts out of the bakery. Runs weekends into November.
Two early hours picking up trash along Route 926 with the Environmental Advisory Council. The kind of morning that counts toward student service hours.
Gay Street is already closed to cars for the market, so the mats go down on the pavement near the post office. Five dollars, one hour, all levels welcome.
The West Chester Growers Market runs Saturday, October 17, 2026, from 9 a.m. to 1 p.m. at the corner of Church and Chestnut Streets in the borough. That is its regular slot every Saturday from May through December; from January through April it shifts to the first, third and fifth Saturdays, 10 a.m. to noon. For parking, the market's site sends you to downtown West Chester's own parking page. This is a producer-only market and the bylaws mean it: vendors sell only what they grow or produce themselves, and anyone who just resells is turned away at the application stage. The weekly roster averages 28 producers from the surrounding region. Expect seasonal fruits and vegetables alongside meats, cheese, local honey, breads, pastries, roasted coffee, local wines and spirits, hard ciders, fresh flowers, bedding plants and prepared foods. The member list runs from Big Sky Bread and Tally Ho Coffee to Society of Bacon, Conebella Farm, Vera Pasta and North Star Orchard, with rotating guests such as Hank's Cinnamon Buns and Rosie's Kettle Corn filling in around them. A Community Tent hosts non-profits and musicians who apply for a spot. The market opened on this same corner in July 1995 with 10 farmers, and its own pitch is a plain one: come and shake the hand that feeds you. Saturday's window is 9 a.m. to 1 p.m., and the shorter winter hours do not start until January.
The West Chester Walking Club picks a different downtown spot each week and sets off at 9:30. Easy pace, no sign up, and some weeks the group ends up in a shop or a cafe.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen in the library community room. Beginners get taught, regulars get a game. No registration, just turn up.
The Uptown's pop-up beer garden with JD Malone playing. Lawn games, drinks, and a stretch of High Street that turns into a patio for the night.
An hour building an eight to ten inch glass terrarium with four plants and decorative bits to arrange. Bring your own bottle, and give yourself fifteen minutes to park.
The farm switches to fall mode for the weekend: hayrides, the corn maze, apple picking and cider donuts out of the bakery. Runs weekends into November.
The last weekend of the season for the street closure. Four blocks of Gay Street without cars, restaurant tables in the road, shops open on either side.
Two hour round trip down the Chester Creek valley to Glen Mills with a long layover at the 1880s station. Pack lunch for the picnic grove or walk over to Red Brick Winery.
The Environmental Advisory Council on what makes a property watershed friendly, from what you plant to where the runoff goes. An hour at the township building on Wilmington Pike.
Last Sunday bingo of September at the Carter Drive taproom, on the standing weekly schedule. Two to four.
Kids eight to twelve dig into three lighthouse keepers who vanished off the Scottish coast, weigh the theories and pick a side. Registration opens September 21.
Fleece strips knotted into a tug toy. If you have a dog, it goes home with you. If you do not, the library takes it to a shelter.
Last one of the season. Free drop in yoga by the historic water tower at Oakbourne Park. All levels, ages sixteen and up. Bring a mat and something comfortable.
September's whiskey and cigar night at Kildare's, seven to nine. Monthly, last Tuesday, on the Gay Street block.
Last Tuesday of September for quizzo at Saloon 151. Eight o'clock, free, 151 W Gay Street.
Last Tuesday of September on the karaoke stage. Same format all year, gift card to whoever the room decides earned it.
Last Wednesday of September on the standing trivia schedule at Levante. Two hours, general questions, taproom seating.
Last Station Jam of September. Seven to eleven on the Market Street stage, players sign up ahead through the venue.
Singer-songwriter Stephanie Philips releases her new album from the Uptown stage on Wednesday, September 30 at 7:30. On a fall calendar thick with tribute acts, it is one of the few nights of original songs.
Last Wednesday of September for quizzo at Barnaby's. Seven thirty, free, High Street.
Last Wednesday of September for music bingo at Saloon 151. Eight o'clock, free, West Gay Street.
Last Wednesday of September on the Side Bar trivia schedule. Eight o'clock on Gay Street.
Last Wednesday of September for pong at Kildare's. Free, ten o'clock, 18 W Gay Street.
A first-Thursday group for writing and workshopping original poems in a friendly critique format. Afternoon session in the library community room, registration through the library.
A rotating bill of stand-up comics in Uptown's smaller room. Doors ahead of the 7:30 start, and the theater sells its own tickets, so skip the resale sites.
Music trivia at the Gay Street pub on Thursdays, eight to ten, and karaoke takes the room straight after until two. Orange crushes are six dollars all day.
Quizzo every Thursday at eight in the Gay Street pub, fifty dollars to the winning table. Well drinks three, craft drafts four, both until ten.
Shops stay open late on the first Friday of the month, with sales and sidewalk activity across the downtown grid. This one doubles as the fall gallery night.
Galleries plus one-night-only pop-up hosts open their doors along the downtown blocks, hanging work by Chester County artists. Free, self-guided, and on-street parking stops charging at 4pm.
Resident artists open the studio on first Fridays, with abstract and realist painting, fabric work and stained glass rotating through. Snacks and drinks are out and the artists are there to talk.
Bring a record, they spin it. Fridays six to ten at the Market Street shop, beer and wine on hand, free to walk in and hand over whatever you dug out.
Two pianos taking requests on the first Friday of every month, seven to ten at the Gay Street pub. The pub tells you to reserve early, so do.
Karaoke at the Market Street bar that already has arcade games, pool tables and shuffleboard. Signups start at 8:50, singing runs nine to midnight, free to join.
Participating bars and restaurants pour $6 fall beers and ciders with seasonal snacks, no ticket needed. Live music between stops, stein-holding contests, and free mini pumpkin painting for kids.
The West Chester Growers Market runs Saturday, October 17, 2026, from 9 a.m. to 1 p.m. at the corner of Church and Chestnut Streets in the borough. That is its regular slot every Saturday from May through December; from January through April it shifts to the first, third and fifth Saturdays, 10 a.m. to noon. For parking, the market's site sends you to downtown West Chester's own parking page. This is a producer-only market and the bylaws mean it: vendors sell only what they grow or produce themselves, and anyone who just resells is turned away at the application stage. The weekly roster averages 28 producers from the surrounding region. Expect seasonal fruits and vegetables alongside meats, cheese, local honey, breads, pastries, roasted coffee, local wines and spirits, hard ciders, fresh flowers, bedding plants and prepared foods. The member list runs from Big Sky Bread and Tally Ho Coffee to Society of Bacon, Conebella Farm, Vera Pasta and North Star Orchard, with rotating guests such as Hank's Cinnamon Buns and Rosie's Kettle Corn filling in around them. A Community Tent hosts non-profits and musicians who apply for a spot. The market opened on this same corner in July 1995 with 10 farmers, and its own pitch is a plain one: come and shake the hand that feeds you. Saturday's window is 9 a.m. to 1 p.m., and the shorter winter hours do not start until January.
The West Chester Walking Club picks a different downtown meeting spot each week for a relaxed morning stroll. Some weeks end with a stop at a shop or a coffee. Weather dependent.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen, beginners and serious players both. No registration. Caregivers of kids ten and under stay on the library premises.
An acoustic set in the East Market Street wine lounge, six to eight. The room was built for listening rather than talking over the music, so pick a glass and sit.
Saturday night karaoke on Market Street, nine until midnight, no cover. Signups open at 8:50, and the arcade games and shuffleboard stay open while you wait.
Ninety minutes through the Chester Creek Valley to Glen Mills and back in heated cars. Layover at the 1880s station with a picnic grove and Red Brick Winery next door. Departures at 10, noon and 2.
Westtown Township's annual community day fills Oakbourne Park for four hours on a Sunday afternoon. The township had not posted the lineup yet, so check its page before you head over.
General knowledge quizzo every Monday from nine to eleven at the Gay Street pub. Fish and chips are ten dollars all day, which is most of the reason to show up early.
Music bingo runs Mondays at nine on High Street, burger specials all day before it. Domestic drafts are four dollars, craft and imports five.
Karaoke with Jexxa runs ten until two on Tuesdays at Barnaby's. Taco specials all day beforehand, five dollar Coronas, nine dollar golden margaritas.
Beer pong tables go up at ten on Wednesdays and stay up until two. Dollar wings all day beforehand, old fashioneds eight dollars.
Music trivia at the Gay Street pub on Thursdays, eight to ten, and karaoke takes the room straight after until two. Orange crushes are six dollars all day.
Quizzo every Thursday at eight in the Gay Street pub, fifty dollars to the winning table. Well drinks three, craft drafts four, both until ten.
Bring a record, they spin it. Fridays six to ten at the Market Street shop, beer and wine on hand, free to walk in and hand over whatever you dug out.
One night of theater in Uptown's Americana Series, paid for by an America250 grant through the Chester County Community Foundation. Curtain at 7:30 on the High Street mainstage.
Original jazz built on Shostakovich, Ravel, Mulgrew Miller and Michael Brecker, played in a recording studio off Prescott Alley. Doors at seven, music at 7:30, twenty-five dollars general admission.
Karaoke at the Market Street bar that already has arcade games, pool tables and shuffleboard. Signups start at 8:50, singing runs nine to midnight, free to join.
The West Chester Growers Market runs Saturday, October 17, 2026, from 9 a.m. to 1 p.m. at the corner of Church and Chestnut Streets in the borough. That is its regular slot every Saturday from May through December; from January through April it shifts to the first, third and fifth Saturdays, 10 a.m. to noon. For parking, the market's site sends you to downtown West Chester's own parking page. This is a producer-only market and the bylaws mean it: vendors sell only what they grow or produce themselves, and anyone who just resells is turned away at the application stage. The weekly roster averages 28 producers from the surrounding region. Expect seasonal fruits and vegetables alongside meats, cheese, local honey, breads, pastries, roasted coffee, local wines and spirits, hard ciders, fresh flowers, bedding plants and prepared foods. The member list runs from Big Sky Bread and Tally Ho Coffee to Society of Bacon, Conebella Farm, Vera Pasta and North Star Orchard, with rotating guests such as Hank's Cinnamon Buns and Rosie's Kettle Corn filling in around them. A Community Tent hosts non-profits and musicians who apply for a spot. The market opened on this same corner in July 1995 with 10 farmers, and its own pitch is a plain one: come and shake the hand that feeds you. Saturday's window is 9 a.m. to 1 p.m., and the shorter winter hours do not start until January.
The West Chester Walking Club picks a different downtown meeting spot each week for a relaxed morning stroll. Some weeks end with a stop at a shop or a coffee. Weather dependent.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen, beginners and serious players both. No registration. Caregivers of kids ten and under stay on the library premises.
The Pumpkin Festival is Saturday, October 10, 2026, starting at 10:00 a.m. at East Goshen Park in West Chester. It is one of the township's annual park events, and the money behind it comes from the Friends of East Goshen, an all-volunteer nonprofit whose page says that fundraising is what lets the township hold its East Goshen Park events at no cost to the participants. No end time, parking plan or rain date is posted, so check the Friends' site closer to the day. The lineup is the reason to come: hay rides, a drawing contest for kids, a family pumpkin carving contest, frozen turkey bowling, a petting zoo and pony rides. There are free pumpkins for the kids, a raffle for the giant pumpkin, and farmers' market vendors. There is also a pumpkin pie eating contest, and the page tells you to enter it, so consider that your invitation. The Friends put attendance at over 2,500 people, which for a township park is a real crowd. One address note: the township's own site lists East Goshen Park at 1661 Paoli Pike, West Chester, PA 19380. Plan around the 10:00 a.m. start, since nothing on the page says how long the day runs.
Eighty artists set up under the trees behind the art association with paintings, sculpture and jewelry. Free to walk through, plus a string quartet, a sound bath, tacos from El Taco Loco and Well Crafted beer.
Advent Lutheran opens its community hall and kitchen for a night of bingo, five until nine, with proceeds going to a local cause. Green Lane, on the south side of town.
Mollie Rose plays a two-hour acoustic set in the East Market Street wine lounge, starting at six. Original material in a room set up for listening.
British rock tribute night with Artful Impact, working through the catalogs that crossed the Atlantic in the sixties and seventies. Saturday at 7:30 on the mainstage.
Saturday night karaoke on Market Street, nine until midnight, no cover. Signups open at 8:50, and the arcade games and shuffleboard stay open while you wait.
Ninety minutes through the Chester Creek Valley to Glen Mills and back in heated cars. Layover at the 1880s station with a picnic grove and Red Brick Winery next door. Departures at 10, noon and 2.
Twenty years in, this one takes over Gay Street for an afternoon of competitive chili from local cooks, hosted by Fiorenza's Food For Friends. Rain date is October 18.
Sunday afternoon acoustic session at the wine lounge, four to six. Earlier and quieter than the Saturday shows, which makes it the easier one to actually hear.
General knowledge quizzo every Monday from nine to eleven at the Gay Street pub. Fish and chips are ten dollars all day, which is most of the reason to show up early.
Music bingo runs Mondays at nine on High Street, burger specials all day before it. Domestic drafts are four dollars, craft and imports five.
A starter soldering kit and a librarian walking you through it, aimed at teens. Open whether you did last year's class or have never held an iron. Registration required and seats are limited.
Karaoke with Jexxa runs ten until two on Tuesdays at Barnaby's. Taco specials all day beforehand, five dollar Coronas, nine dollar golden margaritas.
Beer pong tables go up at ten on Wednesdays and stay up until two. Dollar wings all day beforehand, old fashioneds eight dollars.
A standing get-together for local veterans at Artillery's Barracks taproom off Granite Alley, six to seven. The taproom keeps pouring after the hour is up.
Bring whatever you are making and a drink to sip, third Thursday of the month, free. If you turn up empty-handed there are supplies on hand to get you started.
Music trivia at the Gay Street pub on Thursdays, eight to ten, and karaoke takes the room straight after until two. Orange crushes are six dollars all day.
Quizzo every Thursday at eight in the Gay Street pub, fifty dollars to the winning table. Well drinks three, craft drafts four, both until ten.
Bring a record, they spin it. Fridays six to ten at the Market Street shop, beer and wine on hand, free to walk in and hand over whatever you dug out.
Comedian Josh Blue brings his Road Dog Tour to the Uptown mainstage for one Friday show at 7:30. Tickets only through the theater's own site.
Karaoke at the Market Street bar that already has arcade games, pool tables and shuffleboard. Signups start at 8:50, singing runs nine to midnight, free to join.
The West Chester Growers Market runs Saturday, October 17, 2026, from 9 a.m. to 1 p.m. at the corner of Church and Chestnut Streets in the borough. That is its regular slot every Saturday from May through December; from January through April it shifts to the first, third and fifth Saturdays, 10 a.m. to noon. For parking, the market's site sends you to downtown West Chester's own parking page. This is a producer-only market and the bylaws mean it: vendors sell only what they grow or produce themselves, and anyone who just resells is turned away at the application stage. The weekly roster averages 28 producers from the surrounding region. Expect seasonal fruits and vegetables alongside meats, cheese, local honey, breads, pastries, roasted coffee, local wines and spirits, hard ciders, fresh flowers, bedding plants and prepared foods. The member list runs from Big Sky Bread and Tally Ho Coffee to Society of Bacon, Conebella Farm, Vera Pasta and North Star Orchard, with rotating guests such as Hank's Cinnamon Buns and Rosie's Kettle Corn filling in around them. A Community Tent hosts non-profits and musicians who apply for a spot. The market opened on this same corner in July 1995 with 10 farmers, and its own pitch is a plain one: come and shake the hand that feeds you. Saturday's window is 9 a.m. to 1 p.m., and the shorter winter hours do not start until January.
The West Chester Walking Club picks a different downtown meeting spot each week for a relaxed morning stroll. Some weeks end with a stop at a shop or a coffee. Weather dependent.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen, beginners and serious players both. No registration. Caregivers of kids ten and under stay on the library premises.
Ninety minutes through the Chester Creek Valley to Glen Mills and back in heated cars. Layover at the 1880s station with a picnic grove and Red Brick Winery next door. Departures at 10, noon and 2.
Artisans and vendors set up in Stroud's barnyard with a craft corner, costume contests for kids, adults and dogs, and a masquerade parade near four. Anna Spackman plays acoustic from two, Cheezy Vegan parks a truck.
Free outdoor beer garden on the Uptown lot with lawn games, drinks and live music from five. Stay on for Kashmir inside at 7:30, or just come for the yard.
A Led Zeppelin tribute playing the catalog at full volume. The free beer garden opens on the lot at five, then the band takes the mainstage at 7:30.
Saturday night karaoke on Market Street, nine until midnight, no cover. Signups open at 8:50, and the arcade games and shuffleboard stay open while you wait.
Ninety minutes through the Chester Creek Valley to Glen Mills and back in heated cars. Layover at the 1880s station with a picnic grove and Red Brick Winery next door. Departures at 10, noon and 2.
The Halloween family film on the big screen for a Monday night, part of Uptown's fall movie run. Seven o'clock start on the High Street mainstage.
General knowledge quizzo every Monday from nine to eleven at the Gay Street pub. Fish and chips are ten dollars all day, which is most of the reason to show up early.
Music bingo runs Mondays at nine on High Street, burger specials all day before it. Domestic drafts are four dollars, craft and imports five.
A guided morning walk across Stroud's meadows and woods hunting migrating songbirds, raptors and waterfowl. Bring binoculars. Registration goes through Natural Lands, and the preserve itself is free.
Grades six through twelve paint a small ceramic pumpkin, spooky or realistic, your call. Supplies are limited so each kid registers separately rather than as a group.
Karaoke with Jexxa runs ten until two on Tuesdays at Barnaby's. Taco specials all day beforehand, five dollar Coronas, nine dollar golden margaritas.
A long-running lunchtime book group that meets the third Wednesday of the month in the library community room. The monthly title is posted on the library blog. Registration requested, not required.
Snapology of Downingtown runs a build-and-program hour for ages four to six with a witch as the theme. Registration opens a week ahead and the room fills.
The Philly Keys take requests two pianos at a time and let the room pick what gets played. Runs most months at Uptown, this one on a Wednesday at 7:30.
Beer pong tables go up at ten on Wednesdays and stay up until two. Dollar wings all day beforehand, old fashioneds eight dollars.
The touring Glenn Miller Orchestra plays big band swing on the mainstage, one Thursday night at 7:30. The box office opens two hours before the show.
Quizzo every Thursday at eight in the Gay Street pub, fifty dollars to the winning table. Well drinks three, craft drafts four, both until ten.
Music trivia at the Gay Street pub on Thursdays, eight to ten, and karaoke takes the room straight after until two. Orange crushes are six dollars all day.
Bring a record, they spin it. Fridays six to ten at the Market Street shop, beer and wine on hand, free to walk in and hand over whatever you dug out.
A tribute band working the Genesis catalog plus the Phil Collins and Peter Gabriel solo years. Friday night, 7:30, on the Uptown mainstage.
Karaoke at the Market Street bar that already has arcade games, pool tables and shuffleboard. Signups start at 8:50, singing runs nine to midnight, free to join.
The West Chester Growers Market runs Saturday, October 17, 2026, from 9 a.m. to 1 p.m. at the corner of Church and Chestnut Streets in the borough. That is its regular slot every Saturday from May through December; from January through April it shifts to the first, third and fifth Saturdays, 10 a.m. to noon. For parking, the market's site sends you to downtown West Chester's own parking page. This is a producer-only market and the bylaws mean it: vendors sell only what they grow or produce themselves, and anyone who just resells is turned away at the application stage. The weekly roster averages 28 producers from the surrounding region. Expect seasonal fruits and vegetables alongside meats, cheese, local honey, breads, pastries, roasted coffee, local wines and spirits, hard ciders, fresh flowers, bedding plants and prepared foods. The member list runs from Big Sky Bread and Tally Ho Coffee to Society of Bacon, Conebella Farm, Vera Pasta and North Star Orchard, with rotating guests such as Hank's Cinnamon Buns and Rosie's Kettle Corn filling in around them. A Community Tent hosts non-profits and musicians who apply for a spot. The market opened on this same corner in July 1995 with 10 farmers, and its own pitch is a plain one: come and shake the hand that feeds you. Saturday's window is 9 a.m. to 1 p.m., and the shorter winter hours do not start until January.
The West Chester Walking Club picks a different downtown meeting spot each week for a relaxed morning stroll. Some weeks end with a stop at a shop or a coffee. Weather dependent.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen, beginners and serious players both. No registration. Caregivers of kids ten and under stay on the library premises.
Ride in costume from Market Street to Glen Mills and back, ninety minutes, with treats handed out along the way. Layover at the 1880s station and the picnic grove. Departures at noon and two.
Mariano Mallia takes the Saturday slot at LoCali, six to eight. Acoustic originals in a lounge that keeps the volume where you can still talk.
An hour on Saturday evening building an 8 to 10 inch glass terrarium with four plants and decorative materials to arrange how you like. Bring your own bottle. Give yourself 15 minutes to park.
A Meat Loaf tribute doing Bat Out of Hell and the rest with the theatrics intact. Saturday at 7:30 on the High Street mainstage.
Saturday night karaoke on Market Street, nine until midnight, no cover. Signups open at 8:50, and the arcade games and shuffleboard stay open while you wait.
Ride in costume from Market Street to Glen Mills and back, ninety minutes, with treats handed out along the way. Layover at the 1880s station and the picnic grove. Departures at noon and two.
Ages eight to twelve dig into the case of the Fox Sisters, the three siblings who claimed they could talk to ghosts. Theories, evidence, activities, and a verdict of your own.
General knowledge quizzo every Monday from nine to eleven at the Gay Street pub. Fish and chips are ten dollars all day, which is most of the reason to show up early.
Music bingo runs Mondays at nine on High Street, burger specials all day before it. Domestic drafts are four dollars, craft and imports five.
Karaoke with Jexxa runs ten until two on Tuesdays at Barnaby's. Taco specials all day beforehand, five dollar Coronas, nine dollar golden margaritas.
The older half of the Halloween robotics pair, for ages six to twelve, building Frankenstein's monster with Snapology of Downingtown. Ninety minutes in the community room, registration opens October 21.
The West Chester Halloween Parade steps off at 7 p.m. on Wednesday, October 28, 2026, a school-night parade that West Chester Parks and Recreation runs through the middle of town. The rain date is Thursday, October 29. Admission is free. The route starts at the corner of Church Street and Market Street and makes a loop around downtown. The invitation from Parks and Recreation is to put on your favorite costume and bring the whole family. Candy stations are set up along the route, and each child collects one goodie bag filled with surprises. When the parade finishes, the night keeps going on Market Street with performances from local marching bands and cheer and dance teams. It is a weeknight at the end of October, outdoors, so plan the layers under the costume. Downtown parking is cashless, with garages on East Chestnut Street, South High Street and West Market Street, and it is worth arriving early enough to park and walk to the route before 7. The borough's Parks and Recreation events page lists the rain date, so check it before you head out if the forecast turns.
Beer pong tables go up at ten on Wednesdays and stay up until two. Dollar wings all day beforehand, old fashioneds eight dollars.
Paint night with a pint in hand at Artillery's West Chester taproom, six to ten on a Thursday evening off Granite Alley.
Stand-up night returns to Uptown two days before Halloween, 7:30 start. A rotating lineup of touring and regional comics, tickets through the theater only.
Quizzo every Thursday at eight in the Gay Street pub, fifty dollars to the winning table. Well drinks three, craft drafts four, both until ten.
Music trivia at the Gay Street pub on Thursdays, eight to ten, and karaoke takes the room straight after until two. Orange crushes are six dollars all day.
Bring a record, they spin it. Fridays six to ten at the Market Street shop, beer and wine on hand, free to walk in and hand over whatever you dug out.
Karaoke at the Market Street bar that already has arcade games, pool tables and shuffleboard. Signups start at 8:50, singing runs nine to midnight, free to join.
The West Chester Growers Market runs Saturday, October 17, 2026, from 9 a.m. to 1 p.m. at the corner of Church and Chestnut Streets in the borough. That is its regular slot every Saturday from May through December; from January through April it shifts to the first, third and fifth Saturdays, 10 a.m. to noon. For parking, the market's site sends you to downtown West Chester's own parking page. This is a producer-only market and the bylaws mean it: vendors sell only what they grow or produce themselves, and anyone who just resells is turned away at the application stage. The weekly roster averages 28 producers from the surrounding region. Expect seasonal fruits and vegetables alongside meats, cheese, local honey, breads, pastries, roasted coffee, local wines and spirits, hard ciders, fresh flowers, bedding plants and prepared foods. The member list runs from Big Sky Bread and Tally Ho Coffee to Society of Bacon, Conebella Farm, Vera Pasta and North Star Orchard, with rotating guests such as Hank's Cinnamon Buns and Rosie's Kettle Corn filling in around them. A Community Tent hosts non-profits and musicians who apply for a spot. The market opened on this same corner in July 1995 with 10 farmers, and its own pitch is a plain one: come and shake the hand that feeds you. Saturday's window is 9 a.m. to 1 p.m., and the shorter winter hours do not start until January.
The West Chester Walking Club picks a different downtown meeting spot each week for a relaxed morning stroll. Some weeks end with a stop at a shop or a coffee. Weather dependent.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen, beginners and serious players both. No registration. Caregivers of kids ten and under stay on the library premises.
An hour on Saturday evening building an 8 to 10 inch glass terrarium with four plants and decorative materials to arrange how you like. Bring your own bottle. Give yourself 15 minutes to park.
Saturday night karaoke on Market Street, nine until midnight, no cover. Signups open at 8:50, and the arcade games and shuffleboard stay open while you wait.
The cult classic screens at nine on Halloween night. Uptown runs it as a movie event rather than a plain showing, so costumes are the point.
Ninety minutes through the Chester Creek Valley to Glen Mills and back in heated cars. Layover at the 1880s station with a picnic grove and Red Brick Winery next door. Departures at 10, noon and 2.
General knowledge quizzo every Monday from nine to eleven at the Gay Street pub. Fish and chips are ten dollars all day, which is most of the reason to show up early.
Beer pong tables go up at ten on Wednesdays and stay up until two. Dollar wings all day beforehand, old fashioneds eight dollars.
A first-Thursday group for writing and workshopping original poems in a friendly critique format. Afternoon session in the library community room, registration through the library.
Music trivia at the Gay Street pub on Thursdays, eight to ten, and karaoke takes the room straight after until two. Orange crushes are six dollars all day.
The monthly first Friday run through downtown, with shops keeping later hours and sales on. On-street parking is free after four.
Resident artists open the studio on first Fridays, with abstract and realist painting, fabric work and stained glass rotating through. Snacks and drinks are out and the artists are there to talk.
Bring a record, they spin it. Fridays six to ten at the Market Street shop, beer and wine on hand, free to walk in and hand over whatever you dug out.
Two pianos taking requests on the first Friday of every month, seven to ten at the Gay Street pub. The pub tells you to reserve early, so do.
Karaoke at the Market Street bar that already has arcade games, pool tables and shuffleboard. Signups start at 8:50, singing runs nine to midnight, free to join.
Chester County's original producer-only market, meaning the farmer at the table grew it. Church and Chestnut, every Saturday morning, with baked goods, cheese, eggs and pasture-raised chicken alongside the produce.
The West Chester Walking Club picks a different downtown meeting spot each week for a relaxed morning stroll. Some weeks end with a stop at a shop or a coffee. Weather dependent.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen, beginners and serious players both. No registration. Caregivers of kids ten and under stay on the library premises.
An hour on Saturday evening building an 8 to 10 inch glass terrarium with four plants and decorative materials to arrange how you like. Bring your own bottle. Give yourself 15 minutes to park.
An Eric Clapton tribute with Artful Impact, covering the Derek and the Dominos years through the solo records. Saturday night at 7:30.
Saturday night karaoke on Market Street, nine until midnight, no cover. Signups open at 8:50, and the arcade games and shuffleboard stay open while you wait.
Ninety minutes through the Chester Creek Valley to Glen Mills and back in heated cars. Layover at the 1880s station with a picnic grove and Red Brick Winery next door. Departures at 10, noon and 2.
General knowledge quizzo every Monday from nine to eleven at the Gay Street pub. Fish and chips are ten dollars all day, which is most of the reason to show up early.
The Chester County Food Bank and the library run a cooking and nutrition session built around fresh seasonal ingredients. Ninety minutes in the community room, aimed at adults.
Snapology of Downingtown pairs a story with a hands-on build for ages four to six. An hour in the library community room, registration opens November 4.
Beer pong tables go up at ten on Wednesdays and stay up until two. Dollar wings all day beforehand, old fashioneds eight dollars.
Music trivia at the Gay Street pub on Thursdays, eight to ten, and karaoke takes the room straight after until two. Orange crushes are six dollars all day.
Bring a record, they spin it. Fridays six to ten at the Market Street shop, beer and wine on hand, free to walk in and hand over whatever you dug out.
A YES tribute band playing the long-form prog rock the way it was recorded. Friday at 7:30 on the Uptown mainstage.
Karaoke at the Market Street bar that already has arcade games, pool tables and shuffleboard. Signups start at 8:50, singing runs nine to midnight, free to join.
Chester County's original producer-only market, meaning the farmer at the table grew it. Church and Chestnut, every Saturday morning, with baked goods, cheese, eggs and pasture-raised chicken alongside the produce.
The West Chester Walking Club picks a different downtown meeting spot each week for a relaxed morning stroll. Some weeks end with a stop at a shop or a coffee. Weather dependent.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen, beginners and serious players both. No registration. Caregivers of kids ten and under stay on the library premises.
The November round of Advent Lutheran's bingo night in the community hall, five until nine with the kitchen running. Proceeds go to a local cause.
An hour on Saturday evening building an 8 to 10 inch glass terrarium with four plants and decorative materials to arrange how you like. Bring your own bottle. Give yourself 15 minutes to park.
Saturday night karaoke on Market Street, nine until midnight, no cover. Signups open at 8:50, and the arcade games and shuffleboard stay open while you wait.
The John Candy comedy on the big screen for a Monday night in the fall movie run. Seven o'clock start, tickets through the Uptown box office.
General knowledge quizzo every Monday from nine to eleven at the Gay Street pub. Fish and chips are ten dollars all day, which is most of the reason to show up early.
A long-running lunchtime book group that meets the third Wednesday of the month in the library community room. The monthly title is posted on the library blog. Registration requested, not required.
Ninety minutes of Roblox with Snapology of Downingtown, aimed at ages six to twelve. Held in the library community room on a Wednesday afternoon.
Two pianos, requests from the floor, and whichever player wins the room. The Philly Keys return on a Wednesday at 7:30.
Beer pong tables go up at ten on Wednesdays and stay up until two. Dollar wings all day beforehand, old fashioneds eight dollars.
The November get-together for local veterans at Artillery's Barracks taproom off Granite Alley, six to seven in the evening.
Bring whatever you are making and a drink to sip, third Thursday of the month, free. If you turn up empty-handed there are supplies on hand to get you started.
The November edition of Uptown's stand-up night, 7:30 on a Thursday. Comics rotate each month and the room stays small enough that the front row is a risk.
Music trivia at the Gay Street pub on Thursdays, eight to ten, and karaoke takes the room straight after until two. Orange crushes are six dollars all day.
Bring a record, they spin it. Fridays six to ten at the Market Street shop, beer and wine on hand, free to walk in and hand over whatever you dug out.
Karaoke at the Market Street bar that already has arcade games, pool tables and shuffleboard. Signups start at 8:50, singing runs nine to midnight, free to join.
Chester County's original producer-only market, meaning the farmer at the table grew it. Church and Chestnut, every Saturday morning, with baked goods, cheese, eggs and pasture-raised chicken alongside the produce.
The West Chester Walking Club picks a different downtown meeting spot each week for a relaxed morning stroll. Some weeks end with a stop at a shop or a coffee. Weather dependent.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen, beginners and serious players both. No registration. Caregivers of kids ten and under stay on the library premises.
An hour on Saturday evening building an 8 to 10 inch glass terrarium with four plants and decorative materials to arrange how you like. Bring your own bottle. Give yourself 15 minutes to park.
Saturday night karaoke on Market Street, nine until midnight, no cover. Signups open at 8:50, and the arcade games and shuffleboard stay open while you wait.
General knowledge quizzo every Monday from nine to eleven at the Gay Street pub. Fish and chips are ten dollars all day, which is most of the reason to show up early.
Beer pong tables go up at ten on Wednesdays and stay up until two. Dollar wings all day beforehand, old fashioneds eight dollars.
A 5K run and 2K walk through downtown on Thanksgiving morning, third year running, put on with the West Chester Downtown Foundation. Strollers are fine, pets are not, and it goes ahead rain or shine.
Music trivia at the Gay Street pub on Thursdays, eight to ten, and karaoke takes the room straight after until two. Orange crushes are six dollars all day.
Three days of holiday shopping across more than fifty downtown shops and sixty restaurants, starting the day after Thanksgiving. On-street parking is free all weekend, though lots and garages still charge.
Bring a record, they spin it. Fridays six to ten at the Market Street shop, beer and wine on hand, free to walk in and hand over whatever you dug out.
The Will Ferrell Christmas film screens the night after Thanksgiving at seven, run as a holiday movie event rather than a plain showing.
Karaoke at the Market Street bar that already has arcade games, pool tables and shuffleboard. Signups start at 8:50, singing runs nine to midnight, free to join.
Chester County's original producer-only market, meaning the farmer at the table grew it. Church and Chestnut, every Saturday morning, with baked goods, cheese, eggs and pasture-raised chicken alongside the produce.
The West Chester Walking Club picks a different downtown meeting spot each week for a relaxed morning stroll. Some weeks end with a stop at a shop or a coffee. Weather dependent.
Coach Chuck Shaw runs two hours of chess for kids five to fifteen, beginners and serious players both. No registration. Caregivers of kids ten and under stay on the library premises.
An hour on Saturday evening building an 8 to 10 inch glass terrarium with four plants and decorative materials to arrange how you like. Bring your own bottle. Give yourself 15 minutes to park.
Saturday night karaoke on Market Street, nine until midnight, no cover. Signups open at 8:50, and the arcade games and shuffleboard stay open while you wait.
Ages eight to twelve take on the Amber Room, the gold and amber chamber once called the eighth wonder of the world, missing since the war. Theories, evidence and activities.
General knowledge quizzo every Monday from nine to eleven at the Gay Street pub. Fish and chips are ten dollars all day, which is most of the reason to show up early.
The 28-foot tree lights at 6:30, then the parade steps off at 7 with marching bands, floats, and Santa. A first-Friday-of-December fixture that has drawn crowds to High Street for years.
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Burby
Your dog in the burbs