Top Fall Events in Yates County, NY (2026): Festivals, Wine Dinners & Finger Lakes Fun
Chilly air, vineyard views brushed in reds and yellows, and the scent of fresh-pressed cider or grape juice- fall in the Finger Lakes Countrysides is a season we wait for all year. If you’re searching for the top fall events in Yates County, NY and the surrounding area, this is your guide! Choose from harvest dinners in historic barrel rooms, apple festivals on working farms, live music around Keuka Lake, and small-town traditions you’ll only find here.
Whether you’re planning a Saturday day trip or a cozy overnight escape, here are the can’t-miss events lighting up Yates County this fall- in date order, so you can start planning today.
September: Harvest Season Kicks Off
Wager’s 3rd Annual Apple Festival: Saturday, September 19, 9AM– 5PM
Apple season deserves a proper celebration, and Wager’s Cider Mill (a third-generation, family-owned farm right on East Main Street in Penn Yan) throws one of our favorites. Admission is free, and the day is packed: more than 20 local makers and vendors, free face painting and games for the kids, and tastings throughout the day. Come hungry for mini apple pies, cider donuts, sweet cider, cider slushies and hard cider. A practical tip from locals: vendors accept cash, so tuck some into your pocket before you go. Parking is on Sherman Street, with overflow at the Yates County Fairgrounds.
Mill to Mill 5K/10K and Celebrate Cascade: Saturday, September 19
Lace up for one of the prettiest runs in the Finger Lakes. The third annual Mill to Mill 5K/10K follows the Keuka Outlet Trail between Penn Yan and Dresden, starting and finishing at Cascade Falls. Both distances wind past the scenic Seneca Mills Falls, and 10K runners continue on to the historic Fox Mills site before looping back. Registration is $40 for the 5K and $50 for the 10K, with the race beginning at 10:45 a.m.
The finish line is only the beginning- the race kicks off the 6th Annual Celebrate Cascade, a free trailside party at the Cascade Millsite from 12 – 4PM Expect live music, food hot off the grill, and local food and beverage sampling at one of the most beautiful spots on the trail. Run the race, stay for the festival- or skip the miles and simply join the celebration.
Harvest Dinner at Fox Run Vineyards: Friday, September 25 & October 30th
This gorgeous season deserves a special celebration, and Fox Run Vineyards delivers. Join winemakers Craig Hosbach and Angie Lawler, along with Chef Brud Holland, for a five-course dinner built around local autumn ingredients. Enjoy this guided journey through the building blocks of food and wine pairing in the winery’s historic barrel room overlooking Seneca Lake. Tickets are $125 plus tax and gratuity, and reservations are required (the September date sells out fast- a second Harvest Dinner is set for October 30).
October: Peak Foliage, Peak Fun
Autumn Plein Air Workshop with Kevin Feary: Friday & Saturday, October 2–3
See the season through an artist’s eyes! In this two-day workshop (9:30AM to 4PM), local artist Kevin Feary leads painters outdoors to capture autumn views in oils- the lakes, hills, farms and fields that make the Finger Lakes a natural canvas. It’s a hands-on way to slow down and savor the scenery, hosted by the Arts Center of Yates County.
Downtown Penn Yan Fall Festival: Saturday, October 3rd, 11AM – 4PM
Main Street comes alive with arts and crafts vendors, delicious food, live music and activities for all ages at the Downtown Business Council’s annual Fall Festival; the perfect way to spend an autumn day exploring Penn Yan’s charming downtown shops and eateries between events.
On the Trail of the Friend: A Bus Tour of Public Universal Friend Sites: Saturday, October 3
Step aboard for a journey into one of America’s most fascinating stories. The Public Universal Friend (the Revolutionary-era preacher who founded a settlement right here in Yates County) comes to life on this guided bus tour hosted by the Yates County History Center. The tour departs from the History Center at 107 Chapel Street in Penn Yan at 1:00PM and lasts about an hour and a half; tickets are $50 and include lunch.
Get tickets then read the backstory in our feature, Unraveling History: Yates County and the Public Universal Friend
Harvesting Tradition at Apple Barrel Orchards: October 3 & 4, 10AM – 6PM
Celebrate the rich agricultural heritage of the Finger Lakes at this community event from the Yates County Farm Bureau and Apple Barrel Orchards, a family farm that’s been harvesting its own fruit for over 80 years. Between u-pick apples, fresh cider in the original 1896 farm barn, and hands-on farm fun, it’s a true taste of the countrysides.
Gregory Alan Isakov at Concerts at Point of the Bluff: Sunday, October 4
An unforgettable night of indie-folk under the autumn sky. Gregory Alan Isakov (the Colorado-based horticulturist and songwriter behind six acclaimed studio albums) takes the stage at Concerts at Point of the Bluff, the open-air venue perched above Keuka Lake in Hammondsport. Pair the show with a winery afternoon along the lake and you’ve got the perfect fall evening.
Open House & Apple Festival at the Rochester Folk Art Guild: Saturday & Sunday, October 10–11
One of our most beloved annual traditions returns to East Hill Farm in Middlesex. The Folk Art Guild’s Open House & Apple Festival (11AM to 5PM both days) is free, family-friendly and full of autumn magic: open artist studios with live demonstrations in woodworking and pottery, fresh cider pressed from orchard-grown apples, farmhouse lunches, live music, and the East Hill Gallery stocked with handcrafted work.
Vine to Vessel: Winemaker for a Day at Vineyard View Winery: Saturday, October 17, 2–5PM
One of the most hands-on ways to experience harvest in the Finger Lakes! At Vineyard View Winery, a family-owned, certified sustainable vineyard farmed by Adam and Nikki Folts above Keuka Lake, you’ll load grapes into the press, watch them become fresh, vibrant juice, and be the first to taste the raw, unfiltered potential of the vintage. Then head home with five gallons of your own fresh-pressed juice for winemaking, and reward your efforts with an afternoon of live music, local food and wine. Tickets are $75.
Downtown Penn Yan Trunk or Treat: Saturday, October 24, 4-6PM
Main Street transforms into a family-friendly Halloween celebration! Hosted by the Downtown Business Council, Trunk or Treat brings trick-or-treating right to downtown Penn Yan, complete with a costume parade, a dance party and plenty of treats. It’s free, festive and pure small-town fun.
November: A Toast to the Season
Handcrafted Holiday on the Keuka Lake Wine Trail: Saturday, November 14, 10AM–5PM
On the Wine Trail, the holidays are a season of gathering. Raise your glass and your spirits as you take a self-guided tour of the Keuka Lake Wine Trail’s member wineries, each pouring festive tastings paired with seasonal bites and a behind the scenes peek- the perfect way to kick off the holidays and stock your cellar with local favorites.
Turn a Festival Into a Getaway
As a local, we believe the best way to do fall in Yates County is slowly. Book a night or two in one of our lakeside B&Bs, hotels or campgrounds, and let one event become a whole weekend- a morning hike on the Keuka Outlet Trail, an afternoon of u-pick apples and wine tasting, an evening concert close to the lake. If you’re watching your wallet, our guide to affordable fall escapes rounds up stays starting around $120 a night.
Best of all, we’re closer than most people realize! About 45 minutes from Rochester, two hours from Buffalo and an hour and a half from Syracuse. Plan your getaway with our fall trip ideas, browse more can’t-miss local events. Want seasonal ideas delivered straight to your inbox? Sign up for our newsletter for itineraries, getaway inspiration and insider tips.
Frequently Asked Questions
What are the best fall events in Yates County, NY?
The top fall events in Yates County for 2026 include the Mill to Mill 5K/10K on the Keuka Outlet Trail (Sept. 19), the Harvest Dinner at Fox Run Vineyards (Sept. 25 and Oct. 30), the Rochester Folk Art Guild’s Open House & Apple Festival (Oct. 10–11), Downtown Penn Yan’s Trunk or Treat (Oct. 24), and Handcrafted Holiday on the Keuka Lake Wine Trail (Nov. 14).
When is the best time to see fall foliage in Yates County?
Fall color in the Finger Lakes typically starts through early October and peaks around mid-October. The hillsides around Keuka and Seneca Lakes, the Keuka Outlet Trail, and the country roads between Penn Yan, Dundee and Middlesex offer some of the best leaf-peeping in the region.
Are there free fall events in Yates County?
Yes. The Rochester Folk Art Guild’s Open House & Apple Festival (Oct. 10–11) is free and open to all, and Downtown Penn Yan’s Trunk or Treat (Oct. 24) and Fall Festival are a free family events on Main Street. Many fall happenings at local farms and markets are also free to attend.
What wine events happen near Keuka Lake in the fall?
Fall is wine celebration season on Keuka Lake! Highlights include Harvest Dinners at Fox Run Vineyards on Seneca Lake (Sept. 25 and Oct. 30) and Handcrafted Holiday, the Keuka Lake Wine Trail’s self-guided tasting tour of member wineries, on Saturday, Nov. 14, 2026.