Things to Do in Chester County This Weekend: October 9-11, 2026
Published October 8, 2026 - Updated October 8, 2026
By John Smart (Smarty), A.I. Certified Agent™ with eXp Realty
Chester County starts Saturday, October 10, 2026 with the West Chester Growers Market on North Church Street and Art in the Woods behind the Chester County Art Association, while fall weekends continue at Highland Orchards in West Chester and Milky Way Farm in Chester Springs. Every event below was verified against official event pages, venue sites and local news, with the town, venue, days, times and cost written out so you can plan your weekend.
Saturday, October 10: Market and Art in the Woods
West Chester Growers Market
Town: West Chester
Venue: Corner of N. Church Street and W. Chestnut Street, 201 N. Church St.
When: Saturday, October 10, 9 AM-1 PM
Cost: Free to browse; produce pay-as-you-go
The first producer-only farmers market in Southeastern Pennsylvania runs every Saturday through December, with local growers selling seasonal produce, baked goods and more; see the West Chester Growers Market site.
Art in the Woods
Town: West Chester
Venue: Woods behind the Chester County Art Association, 100 N. Bradford Avenue
When: Saturday, October 10, 11 AM-4 PM
Cost: Free and open to all
The Chester County Art Association transforms the woods behind its building into a strolling outdoor art show with about 80 local artists selling handmade work, plus food trucks and music; details are on the Chester County Art Association page.
Fall Weekends at Chester County Farms
Highland Orchards Fall Fest Weekends
Town: West Chester
Venue: Highland Orchards, 1000 Marshallton-Thorndale Road
When: Saturdays and Sundays in the fall, 9 AM-5 PM
Cost: Pay-as-you-go for picking, hayrides and activities
Fall Fest Weekends at Highland Orchards include pumpkin patch picking, apple picking, hayrides, an apple cannon, face painting and a Levante beer garden, with the farm market and bakery's famous pies and apple cider donuts; see the Visit Philadelphia fall farms roundup.
Milky Way Farm Pumpkin Harvest Season
Town: Chester Springs
Venue: Milky Way Farm, 521 E. Uwchlan Avenue
When: Saturdays and Sundays through October 31, 10 AM-5 PM
Cost: Pay-as-you-go for activities
Pumpkin patch picking, a corn maze, hayrides and animal visits fill the harvest season at this dairy farm, whose on-site creamery serves homemade ice cream; see the Milky Way Farm Pumpkin Harvest page.
Frequently Asked Questions
What's happening in Chester County this weekend, October 9-11, 2026?
Saturday, October 10 has the West Chester Growers Market in the morning and Art in the Woods in the afternoon. Fall weekends continue at Highland Orchards in West Chester and Milky Way Farm in Chester Springs, with hayrides, cider donuts and pumpkin picking.
What can families do in Chester County this weekend?
Highland Orchards and Milky Way Farm both offer pumpkin picking, hayrides and corn mazes on weekends, and Art in the Woods is a free, family-friendly stroll through a wooded outdoor art show with food trucks.
Are there any free events in Chester County this weekend?
Art in the Woods is free and open to all, and the West Chester Growers Market is free to browse. The farm activities at Highland Orchards and Milky Way Farm are pay-as-you-go.
What festivals are happening in Chester County this weekend?
Art in the Woods is the weekend's dedicated festival in West Chester, while Highland Orchards and Milky Way Farm run their fall weekend programs with pumpkin picking, hayrides and seasonal activities.
Smarty's Pick: Art in the Woods
My pick for Chester County this weekend is Art in the Woods on Saturday, October 10, 11 AM-4 PM in West Chester. It is free, family-friendly and completely different from the usual fall fair: about 80 local artists set up in the woods behind the Chester County Art Association, with food trucks and live music. Pair it with the West Chester Growers Market in the morning and you have a full, easy day downtown.
A Note on Plans: Confirm Before You Go
Event times, parking, vendors and ticket prices can shift as the weekend gets closer, so confirm details with each organizer before you head out. A quick check of the official event pages linked above is the best way to avoid a closed gate or a sold-out entry window.
Make a Weekend of It: Scout a Neighborhood
Festival weekends are also a great time to explore a town you might call home. Notice how the streets feel, whether parking is easy, and whether the shops and restaurants match your routine. For honest, local guidance on which communities fit your wish list, schedule a chat with Smarty, and compare the rest of the region in our Philadelphia Region weekend guide.
Connect with Smarty
John Smart, known as Smarty, is an A.I. Certified Agent™ with eXp Realty and the founder of Smarty Home Solutions, serving Greater Philadelphia and the Delaware Valley with more than 30 years of real estate experience. Whether you are buying, selling or just scouting a neighborhood, he can help you make a smarter move.