Water & Wine Weekly • Penn Yan, New York • September 28-October 4, 2026 • Issue 18
Fall in Love with
Penn Yan
As we head into October this week the air is crisp, the leaves are beginning to change, and Penn Yan is a lovely location for a fall visit.
The vineyards are busy working on harvest and pumpkins are filling roadside farm stands. Head out for a U-Pick adventure! Grab the family for apple picking, grape harvesting or pumpkin patch exploring. Check out Newsletter Issue 17 for a list of our favorite Local U-Pick Farms.
But the highlight this week is the annual Downtown Fall Festival in Penn Yan! On Saturday get ready to sip, savor & shop right on Main Street with local vendors, a beer garden, and food trucks to bring you seasonal flavors. Its the perfect place to celebrate fall! Keep reading for all the details and fun.
Celebrate Autumn on Main Street
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. Read more here…
Make It a Weekend on Main
Your curated itinerary for a fabulous fall weekend in Penn Yan:
Friday Evening:
Arrive in Penn Yan, check into your favorite local Bed and Breakfast. Have a stroll on Main Street for First Friday to shop, have a glass of wine, and a fine chef inspired meal.
Sip: Have a pre-dinner glass of wine at the Burnt Rose Wine Bar, an upscale-casual Penn Yan favorite that pairs a creative, globally inspired menu with a thoughtfully curated selection of Finger Lakes wines and craft cocktails. With its warm, inviting atmosphere and emphasis on fresh, locally sourced ingredients, it’s a wonderful spot for a memorable dinner or relaxed brunch in the heart of downtown.
Burnt Rose Wine Bar
Location: 13 Main St, Penn Yan, NY 14527
Phone: 315-924-3000
Website: https://burntrosewinebar.com/
Savor: For an upscale plate, have dinner at the 18th Amendment. A cozy, chef-driven restaurant and craft cocktail bar in downtown Penn Yan, known for its creative, seasonal dishes made with locally sourced ingredients. Its intimate, speakeasy-inspired atmosphere and inventive cocktails makes it’s a wonderful choice for a special dinner in the Finger Lakes.
18th Amendment Kitchen & Cocktail Bar
Location: 7 Main St, Penn Yan, NY 14527
Phone: 315-694-9032
Website: http://18thamendmentkitchencocktailbar.com/
Shop: On the first Friday of the month, participating businesses stay open later, creating an easygoing evening filled with shopping, food, drinks, art, music, and plenty of local conversation. The event typically runs from 5–8 p.m., giving visitors and locals plenty of time to wander Main Street, pop into their favorite shops, discover something new, and support the small businesses that make Penn Yan such a fun Finger Lakes destination. First Friday is a wonderful way to experience Penn Yan like a local.
First Friday on Main Street by the Downtown Business Council
Website: https://downtownbusinesscouncilpy.com/first-fridays-1
Stay: The Finger Lakes Bed and Breakfast at Hutton Farm - a 1840’s Italianate home on seven acres located within walking distance to the Main Street.
Finger Lakes Bed and Breakfast at Hutton Farm
Location: 128 South Avenue, Penn Yan
Phone: 315-536-8070
Website: https://www.fingerlakesbb.com/
Saturday Morning:
Savor: Grab a hearty breakfast to fuel up for the day at the Wagner Restaurant. My pick is a buckwheat pancake or a McJohn breakfast sandwich. Sip on a cup of Joe or the full service bar offers Bloody Mary’s and mimosas.
Wagner Restaurant
Location: 124 E Elm St, Penn Yan, NY 14527
Phone: (315) 536-8062
Saturday Late Morning:
Experience: Head to the Downtown Fall Festival beginning at 11am on Saturday. Stroll Main Street, shop the vendors, listen to live music, watch the glass-blowing demonstrations, browse the artisan booths and let the kids enjoy the festival activities.
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
Savor: The festival offers food trucks parked along Main Street for when the hunger strikes. Grab a sausage from 3 Rivers Hots & Brats and a delightful cone from Seneca Farms, a local favorite offering homemade ice cream.
Saturday Late Afternoon:
After you wrap up with the Fall Festival festivities, make your way over to the Main Street bridge and head down the steps to the Keuka Outlet Trail. Talk a walk to burn off the lunch and desert calories. Head east to walk a wood gravel path toward the falls or head west for a paved walk.
Saturday Evening:
Come back downtown for a night out on Main. Sip on a pint at Laurentide Brewery, have a casual dinner at Parker’s Grille, and complete the evening with a night cap at to finish the day on Main Street.
Sip: Have a locally crafted pint at Laurentide Brewing Company. Hand crafted beers, local spirits and wines available. Set in a beautifully preserved carriage house at The Laurentide Inn. Fall flavors are in full swing with specialty cocktails and darker ales on tap.
Laurentide Brewing Company
Location: 12 Maiden Lane, Penn Yan, NY 14527
Phone: (315) 694-7605
Website: https://thelaurentidebeer.com/
Savor: For a casual dinner head to Parker's Grille, serving classic pub favorites, smash burgers, sandwiches, wings, and wood-fired pizzas. With a casual atmosphere, full bar, and sports-bar vibe, it’s a fun spot to grab a bite, enjoy a drink, and unwind after a day exploring the Finger Lakes.
Parker's Grille - Penn Yan
Location: 11 Main St, Penn Yan, NY 14527
Phone: 315-227-2494
Website: https://www.parkersgrilleinc.com/
Why We Love Fall in Penn Yan
The Penn Yan Fall Festival is the kind of event that reminds us why we love small towns in the Finger Lakes.
It's not just about the festival. It's about spending the day wandering Main Street, discovering a shop you didn't know existed, chatting with local makers, listening to live music, eating something delicious and watching the village take on that unmistakable golden glow of October.
So grab your sweater, bring your appetite and leave a little room in the car for your shopping finds.
Weekly Events List
10am • Creating with Oils with Steve Duprey • Arts Center of Yates County
10am-5pm • Pretzel & Wine Pairing • Fulkerson Winery
11am • Vineyard Hike & Tasting • Lakewood Vineyards
11am-4:30pm • Tabora Cookie & Wine Pairings • Tabora Farm & Winery
5-7pm • Open Mic • Abandon Brewery
5-8pm • Live Music, Wine, and Beer with Logan Route Music • Glenora Wine Cellars
5-8pm • Open Mic Night • Keg & Barrel
6-8pm • Name That Tune Bingo • Outlet 111
9:30am • Autumn Plein Air Workshop with Kevin Feary • Arts Center of Yates County
10am-5pm • Pretzel & Wine Pairing • Fulkerson Winery
10am-5pm • Wine & Pickle Pairing • Toast Winery
11am • Vineyard Hike & Tasting • Lakewood Vineyards
11am-4:30pm • Tabora Cookie & Wine Pairings • Tabora Farm & Winery
3pm • Open Doors: Farm Tour • Hermann J. Wiemer Vineyard
3-6pm • Live Music with John Bolger • Castle Grisch Winery
4-7pm • Live Music Friday with Better Halves • Weis Vineyards
5-7pm • The Beerocracy Brit Social at the Pub • Seneca Lake Brewing Company
5-8pm • Farm Dinner Series • Dean Lane Dining
5-8pm • Live Music with Jim E Leggs Trio & Foodtruck by JRs BBQ • Keuka Lake Vineyards
6-8pm • Fire Pit Friday Nights - Food, Music, Cigars & S'mores • Krooked Tusker Distillery
8am-12pm • Green Doctors Farmer’s Market • Lake Street Plaza
8am-4:30pm • Fall Fest & Farmer’s Market & More • The Windmill Farm & Craft Market
9am • Saturday Yoga • Hunt Country Vineyards
9am-1pm • Farmer's Market • Yates County Office Building
9am-4pm • Welding & Blacksmithing Workshop (Pre-Registration Req'd) • Hunt Country Vineyards
9am-6pm • Harvesting Tradition with Yates County Farm Bureau • Apple Barrel Orchards
10am • Guided Wine Tour • Lakewood Vineyards
10am-3pm • Chicken BBQ • Oak Hill
10am-5pm • Pretzel & Wine Pairing • Fulkerson Winery
10am-5pm • Wine & Pickle Pairing • Toast Winery
11am-4pm • Downtown Fall Festival • Main Street Penn Yan
11am-4:30pm • Tabora Cookie & Wine Pairings • Tabora Farm & Winery
11:30am-2:30pm • Live Music with Nates Michaels • The Windmill Farm & Craft Market
1-6pm • Food Truck by Cousins Maine Lobster • Krooked Tusker Distillery
3-6pm • Live Music with Adam Knows • Krooked Tusker Distillery
9am-4pm • Welding & Blacksmithing Workshop (Pre-Registration Req'd) • Hunt Country Vineyards
9am-6pm • Harvesting Tradition with Yates County Farm Bureau • Apple Barrel Orchards
10am-5pm • Sparkling Sundays • Glenora Wine Cellars
10am-5pm • Pretzel & Wine Pairing • Fulkerson Winery
10am-5pm • Wine & Pickle Pairing • Toast Winery
11am-3pm • Boozy Coffee Flights • Krookid Leyk Distilling
11am-3pm • Sunday Brunch • Castle Grisch
11am-4:30pm • Tabora Cookie & Wine Pairings • Tabora Farm & Winery
1pm • Guided Wine Tour • Lakewood Vineyards
1-4pm • Live Music with Over Easy Afternoons with Connie • Apple Barrel Orchrds
1-6pm • The British Sunday Roast & Brit Car Sunday Social • Seneca Lake Brewing Company
Thank you for reading another issue of Water & Wine Weekly! Enjoy your weekend and I hope to see you at the Penn Yan Downtown Fall Festival!!
Claudia
Curating your experience in Penn Yan, New York
