Penny Carlton / October 31, 2025
Penn Yan’s Fall Festival:Where Community, Color & Cheer Come Together
There’s a touch of enchantment that drifts down Main Street in Penn Yan when autumn’s last leaves twirl in the breeze and the November air shimmers with that crisp, golden kind of magic you can almost taste. Coffee cups warm chilly hands, laughter bounces between shopfronts, and neighbors greet one another as if no time has passed since summer. That’s the spirit of the Penn Yan Fall Festival—a day when the heart of Keuka beats to the rhythm of fiddles, laughter, and falling leaves.
🎉 A Festival Growing in All the Right Ways
After a successful first year of focused growth in 2024, the Downtown Business Council of Penn Yan (DBC) is thrilled to bring back the Fall Festival even bigger and better for 2025! This year’s celebration features an additional live band, a brand-new beer tent, more food options, and 15 extra arts, crafts, and non-profit booths—all designed to make this cherished community event the best one yet.
Historic Downtown Penn Yan has never looked more inviting. Recent upgrades and renovations have brought a fresh glow to the village while preserving every bit of its old-fashioned charm. The result is a Main Street that feels both renewed and timeless—a place where history and hometown spirit come together in a way that feels straight out of a Norman Rockwell painting, warm and full of life beneath the golden light of fall.
🎶 Music, Merriment & Main Street Magic
Two beloved local bands will perform throughout the day, filling both ends of Main Street with lively music and hometown rhythm.
🎵 The Decades Band and Black Robin Band will keep the crowd smiling, dancing, and singing along all afternoon.
The Food Truck Roundup will roll into Jacob’s Street at Main, bringing a tempting variety of eats to pair with your cider or local brew. Downtown restaurants and watering holes along Elm, Main, and Liberty Streets will also be open, serving up seasonal specialties and cozy indoor seating for those looking to take a break from the bustle.
🎠 Family Fun & Small-Town Whimsy
Kids are at the heart of this festival, and there’s plenty to keep them laughing and exploring. The Kids’ Area Booths include a crafting tent, face painting, darts, bean bag throw, bounce house, and cotton candy stand—guaranteed to spark giggles and sticky fingers alike.
Over in the games section, visitors can test their skills at axe throwing, cornhole, and hay wagon rides, or stop by to visit the friendly alpacas for petting and even horses for riding. The festival wouldn’t be complete without a little friendly competition—so don’t miss the Scarecrow Contest, where creativity and community pride take center stage in one of the most beloved fall traditions.
🍁 Shop, Savor & Stroll
The festival’s footprint stretches across Main Street, right in the heart of downtown Penn Yan. Adjacent parking lots offer convenient one-block walkways to the event area, making it easy for everyone to join in. The entire festival is free and open to the public, and handicapped accessible—because when our community comes together with visitors from near and far, everyone belongs.
Be sure to stop in and see our local merchants while you’re there — each one adds its own special charm to the spirit of Main Street. Step inside Long’s Cards & Books, a beloved local treasure where generations have discovered stories, laughter, and the perfect greeting card. Follow the sweet scent down the street to Keuka Candy Emporium, where glass jars brim with colorful nostalgia and the joy of childhood memories. Then cozy up at Amity Coffee Co., a favorite gathering spot where the aroma of freshly brewed coffee mingles with the hum of friendly conversation.
And while you’re strolling, consider taking a moment to drop off a non-perishable food donation at Simplicity on Main — a simple act of kindness that helps support local families as the holidays approach.
Each shop along Main Street tells its own story, stitched together by the shared warmth and hospitality that make Penn Yan shine year-round. With Main Street closed to traffic, you can wander at your own pace, pausing to chat with friends, admire the fall décor, or simply soak in the details of this charming, historic village. Every window display, every brick storefront, and every friendly wave feels like a page from a living storybook — one you’ll be glad to be part of.
🌾 Why We Love It — and Why It Matters
The Penn Yan Fall Festival is more than an event—it’s a celebration of who we are. It brings together the farmers, makers, musicians, and dreamers who shape the stories of our small towns. Each booth, each melody, and each smiling face reflects the spirit that makes the Keuka region so extraordinary.
Here at Keuka Roots, we love nothing more than seeing our communities flourish through events like this—moments that remind us of the beauty in connection, creativity, and shared laughter. Whether you come for the music, the food, or the sheer nostalgia of it all, you’ll leave with pink cheeks from the autumn air and a heart full of small-town warmth.
📍 Save the Date
Penn Yan Fall Festival
🗓 Saturday, November 1, 2025
🕚 11 a.m. – 4 p.m.
📍 Main Street, Downtown Penn Yan, NY
Hosted by the Downtown Business Council of Penn Yan
In partnership with the Yates County Chamber of Commerce
🎟 Free to the public | Handicapped accessible | All are welcome!
