The Best Things To Do Around The Main Line with Kids
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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Main Line Parent Community Calendar
Downtown West Chester Gay Street Open-Air Market
The Gay Street Open-Air Market returns for 2026 from Friday, May 1st to Sunday, September 27th!
The Open-Air Market was created during the pandemic to give residents and visitors more space to shop, eat, and explore town. Now, it has become one of our most popular events! Each year, four blocks of Gay Street (from Matlack Street to Darlington Street) are closed to vehicles so everyone can partake in al fresco dining and shopping. Restaurants extend into the street, so you can enjoy the beautiful weather as you eat.
This year, Gay Street will be shut down for the Open-Air Market every weekend (Friday morning through Monday morning). Gay Street will remain closed to vehicles on Monday holidays (Memorial Day and Labor Day) and start a day early on Thursdays ahead of Friday holidays (Juneteenth and Independence Day).
