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Annual Events-at-a-Glance

Unless otherwise noted, all events take place in downtown West Chester.

>> Dates may change without notice. To see all events in West Chester, go to Events Calendar and DowntownWestChester.com.

HELP SAVE OUR HISTORY - VOTE FOR CCHS! Downtown West Chester and the Chester County Historical Society have been invited to participate in a national voting campaign sponsored by the National Trust for Historic Preservation and American Express. West Chester is the only PA community to join 19 other finalists throughout the country. Voting is easy! Just visit the website, select West Chester (CCHS), sign in, and vote 5 times each day! #VoteYourMainStreet #UnderOneRoof

Click here to download the 2019 Downtown Events list (PDF).

Weekly/Monthly Events:

  • First Fridays -- Stores are open late the first Friday of each month with specials and more. Free parking at street meters after 5pm.

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2019 Events

Benchmark Twilight Cycling Classic -- August 10 2019, 3pm to 10pm. Watch as top athletes race the streets of West Chester up to 35 mph.

West Chester Al Fresco -- September 5, 2019, 6:30 to 9:30pm. Details TBD.

Chester County Restaurant Festival -- September 15, 2019, Noon to 5 pm. Huge selection of food trucks, vendors, and more.

Autumn Gallery Walk -- October 4, 2019. 5pm-9pm. Enjoy one-night-only art exhibits and special events throughout downtown.

West Chester Rotary's Annual Chili Cook-off -- October 13, 2019, 10am to 3:30pm. Vote for the best chili in West Chester!

Halloween Parade -- October 23, 2019, 7:00pm. Bring your little monsters downtown to check out the costumes, candy, and fun!

Veterans Day Parade -- November 4, 2019, 2:00pm. Parade along East Gay Street with Memorial ceremony at 2pm.

Shop Small West Chester WEEKEND -- November 29 - December 1, 2019. Support your local businesses by shopping local this holiday season with lots of great sales, giveaways, and more!

QVC West Chester Christmas Parade -- December 6, 2019. Festivities begin at 5pm, and the Christmas Parade begins at 7:15pm.

2020 Events

West Chester Film Festival -- April 24-26, 2020. Award winning short films all throughout town!

Spring Gallery Walk -- May 1, 2020, 5pm-9pm. Enjoy one-night-only art exhibits and special events throughout downtown.

May Day Festival of the Arts -- May 3, 2020, 11am to 4pm, at Everhart Park. Free for the whole family.

Up On The Roof -- June 6, 2020, 7pm to 11pm. A fundraising event on the roof of the Chestnut Street Parking Garage to benefit the WCDF.

Swingin' Summer Thursday -- July 8, 2020, Street festival with live music and fun for the whole family. Free to attend. 6:30pm to 9:30pm.

Turks Head Music Festival -- July 12, 2020, 11:00am to 5:00pm at Everhart Park. Free for the whole family.

West Chester Al Fresco -- August 6, 2020, 6:30 to 9:30pm. Details TBD.

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Call 610.738.3350 or fax 484.843.2250