Celebrate Autumn on Main Street this Fall

Sep 29

There’s something about October in Penn Yan. The air gets crisp, the leaves begin showing off their best colors, and Main Street comes alive with the sights, sounds and flavors of fall.

If you’re looking for a fun Finger Lakes getaway the first weekend of October, make plans for the Downtown Fall Festival on Saturday, October 3, 2026, from 11 a.m. to 4 p.m. The festival takes over Main Street in downtown Penn Yan, with the street closed to traffic and filled with local makers, food, music and plenty of family-friendly fun.

And the best part? The festival is just the beginning. Give yourself a full day to wander downtown, shop the local stores, grab lunch, enjoy a little live music and maybe finish the afternoon with a sweet treat—or a glass of Finger Lakes wine.

What You'll Find at the Fall Festival

Main Street becomes the center of the action during this annual celebration of autumn and community

The 2026 festival features arts and crafts vendors, food trucks and specialty food booths, live music, a beer garden, horse rides, hayrides, children's activities, corn hole, glass-blowing demonstrations and farm animals.

For music lovers, Black Robin Band and solo acoustic artist John Bolger will provide the soundtrack for the afternoon, and the music is free to enjoy.

There’s also a little something special happening at the four corners of Main Street: Magpie Glass Blowing will offer free hourly glass-blowing demonstrations. Watching a piece of glass transform right before your eyes is the kind of unexpected little experience that makes a small-town festival memorable.

Fun for Families

The free Kids' Korner includes a make-and-take craft, scarecrow bean bag toss, face painting, cotton candy and games. There will also be free hayrides and a petting zoo including goats, small farm animals and alpacas.

And don't be surprised if the horses become a highlight of the day. Mountain Rose Horse Farms will be offering horse rides during the festival.

Sip Local at the Beer Garden

The festival brings a Beer Garden experience this year for adults. Sip on local beers and other canned beverages, and sit back and relax with friends. Proper ID is required.

Make Time to Shop Downtown

One of the best things about visiting the Penn Yan Fall Festival is that you're already in the middle of one of the Finger Lakes' most walkable small-town shopping districts.

Take your time wandering Main Street and popping into the local shops between festival activities.

For something sweet and nostalgic, stop at The Keuka Candy Emporium, where you'll find retro candies, handmade chocolates, fudge, ice cream and plenty of treats that are difficult to leave behind.

Music lovers should make a stop at WaxPax Records, a downtown record shop with new and used vinyl and plenty to browse for both serious collectors and casual music fans.

Looking for something for your home? Staving Artist Woodwork offers locally made woodwork and gifts, while The Potters' Gallery showcases handmade pottery and ceramics from artists.

Garden lovers will want to wander into Plants on Main, a charming shop filled with houseplants, gardening goodies and unique gifts.

And for books, clothing, gifts and a little more browsing spend a little time in Longs' Cards & Books, you’ll find everything under the sun in this local favorite.

Savor Your Fall Festival Day

Of course, all that shopping and exploring works up an appetite!

The Fall Festival itself will have food vendors including Rise & Thrive Coffee Company, 3 Rivers Hots & Brats, Seneca Farms, Girly Pops FLX, Aumick's Eats, Honey Bee Home Bakes and Jenny Drink-Ups.

But don't feel like you have to eat only from the festival booths. One of the best ways to experience Penn Yan is to support one of the locally owned restaurants downtown.

For a casual meal right on Main Street, consider Keuka Restaurant or Parker's Grille.

If you're looking for something a little more elevated, Burnt Rose Wine Bar & Restaurant and 18th Amendment are both right in the downtown area.

Turn Your Festival Day Into a Finger Lakes Getaway

If you're coming from out of town, why stop with the festival?

Penn Yan sits right between Keuka Lake and Seneca Lake, making it an easy home base for a fall weekend filled with wine, food, shopping and scenery.

After the festival, you could take a scenic drive along the lake, visit a nearby winery or simply enjoy the changing leaves. The Keuka Lake Outlet Trail is another beautiful option if you'd like to stretch your legs and take in some autumn scenery around the water.

And, of course, fall in the Finger Lakes is wine country at its most beautiful. The vineyards are fully into harvest season, making October a wonderful time to combine a Penn Yan visit with a wine-tasting adventure.

Downtown Penn Yan Fall Festival

Saturday, October 3, 2026

11 a.m.–4 p.m.

Main Street, Downtown Penn Yan

https://downtownbusinesscouncilpy.com/fall-festival

Free admission

Festival details and participating vendors can change, so check the Downtown Business Council of Penn Yan's event information before heading out.

Claudia Milroy

Thank you for stopping by! I hope you stay awhile and come back often. I started the weekly newsletter and this website for tourists and locals alike. I once was a tourist (over a decade ago) and now I’m a local, living here, working here, raising a family here! And I sure do love it!

Naturally I first fell in love with the rolling hills and cool lake breezes. But as I returned again and again, for a different season and different reason, Penn Yan stuck with me. I recall first it was the hint of grape when you drive by a vineyard and then the caramelized, roasted air that wafted down Main Street from Birkett Mills. Visit after visit my husband and I hit all the tourists stops because of my curiosity. Full disclosure - my husband was raised in Penn Yan and he knew all the ins and outs of the area to woo me! Travel & history nerd here! So, through our years of dating and early years of marriage (p.s. we got married in the Finger Lakes!) we would visit family, friends, and our favorite spots. Then the day came when our son was just 6 months old and we decided it was time to move to Penn Yan! Now 10 years later I’m here to share my love of this place with you!

I hope you enjoy this, I hope you take away some cool and fun inspiration for your next adventure. If you're planning a trip, please don’t hesitate to reach out - I’d love to personalize an experience or a 7 day itinerary for you.

https://waterandwineweekly.com