Gay Street Open Air Market 2026
Downtown West Chester N. High and Gay Street, West ChesterThe Gay Street Open-Air Market returns for 2026 in Downtown West Chester.
Discover the best family-friendly things to do in and around the Main Line with kids, including events, festivals, attractions, and free activities through our curated calendar. Find what’s happening in Chester, Delaware, and Montgomery Counties today and plan your next family adventure!
💞 Check out our sister Community Calendars too: Philadelphia Family and Bucks County Parent.
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The Gay Street Open-Air Market returns for 2026 in Downtown West Chester.
The Gay Street Open-Air Market returns for 2026 in Downtown West Chester.
Colonial history will come to life in Tredyffrin Township this September when His Majesty’s 40th Regiment, 2nd Battalion Light Infantry – the “Bloodhounds” – establishes an authentic Revolutionary War encampment at Teegarden Park in Tredyffrin Township as part of Chester County’s 250th anniversary celebration.
Kick off the fall semester with an afternoon of fun, flavor, and community at Creutzburg! The community is invited to join Main Line School Night on Saturday, September 19, from 12:00–4:00 pm for an afternoon filled with tasty bites, local artisans, live music, games, dance, and hands-on demonstrations from MLSN instructors. Whether attendees are 9 or 90, there will be something for every lifelong learner!
The Borough of Conshohocken invites you to the 33rd Annual Funfest on Saturday, September 19, from noon to 8 p.m., taking over Fayette Street for a celebration bigger and better than ever before.
Enjoy Baby Whale and the Plastic Ocean during the 2026 Philadelphia Fringe Festival!
The HEADstrong Foundation is bringing its Running aHEAD of Cancer 5K back to Swarthmore this fall. Runners, walkers, and supporters are invited to come together for a 5K run and 1-mile walk. Kids and strollers are welcome, making the event open to the whole family. The event supports HEADstrong’s mission and Nick’s House, which provides free accommodations and support to families traveling for cancer treatment.