2nd Annual West Chester Holiday Shop & Stroll
A second-year holiday shopping stroll on Sunday, November 15, from noon to 5 p.m. Check in at La Chic Boutique between noon and 2 for a wristband, bingo card and map. Over 20 stores each offer a discount, treat or surprise for the group, and a stamp for your card. Fill the card to enter the raffle basket. The afternoon wraps up at 9 Prime, where a private room opens at 3:30 and winners are drawn at 4:30. Free, but reserve a spot on Eventbrite.
More at Downtown West Chester
Saturday Morning Walks 2026
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.
West Chester Halloween Parade
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.
Saturday Morning Walks 2026
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.
Around the same time
Free Tours for Veterans
Veterans and active-duty military plus their families tour the historic village, the Thompson-Neely house and grist mill, or climb Bowman's Hill Tower at no charge. Bring a military ID.
Bookbinding Level 1 Workshop
A hands-on bookbinding class in the village's Book Bindery, one of the last two Level 1 sessions of 2026. Pre-registration is required and classes fill quickly. Sign up through Historic Sugartown.
Free Tours for Veterans
Veterans and active duty military with an ID walk the Historic Village or the Thompson-Neely House and Grist Mill at no charge, families included, plus free admission to Bowman's Hill Tower. The mill tour needs advance registration.
