Water & Wine Weekly • Penn Yan, New York • October 5-11, 2026 • Issue 19
There’s something special about autumn in the Finger Lakes—the crisp air, brilliant foliage, and the unmistakable feeling that it’s time to slow down and savor the season.
It’s a fantastic time to follow the wine trails. Harvest is underway, the vineyards are changing color, and many wineries continue to offer live music, food pairings and special experiences. Distilleries are celebrating too - by the campfire with s’mores and hand crafted cocktails!
Fall activities and scenery is at every turn. Try the Sky Ride, take a harvest hike, or wander a corn maze. The fall season changes quickly and often feels so short. Get out and about, enjoy the Fall in the Finger Lakes!
Fall Foliage, Festival Fun & Finger Lakes Views
This weekend, one of the region’s best vantage points for taking it all in will be buzzing with activity as Bristol Mountain Ski Resort hosts its 2026 Fall Festival on October 10 and 11.
Running from 11 a.m. to 5 p.m. both Saturday and Sunday, the festival brings together fall scenery, live entertainment, food, vendors, and family-friendly activities in the Bristol Hills. The star attraction, of course, is the Fall Sky Ride, which carries visitors toward the summit for sweeping views of the changing landscape.
Keep reading for all the details and fun here… Read more here…
Your Curated Weekend Itinerary
The Holiday weekend offers us plenty of time to slow down and savor the season. Here is one way to enjoy the offerings this weekend:
A Friday Fall Evening
Sip and Savor at a local winery or distillery Friday evening. Head out to Keuka Lake Vineyards for their Happy Hour Concert Series from 5-8pm to listen to Live Music with Dave Peterson and savor the local flavor with Rays' Mobile Food offering wraps, burgers and gyros. For a versatile wine, sip on their Semi-Dry Riesling offering aromas of honeyed almonds, caramelized apricots and yellow plums that finishes on a note of almond blossoms.
Keuka Lake Vineyards is a beautiful winery in New York’s Finger Lakes region, known for its scenic views and award-winning wines. Visitors can enjoy a relaxing tasting experience while taking in the natural beauty of Keuka Lake. Dog friendly and accepts large groups with a reservation.
Location: 8882 Co Rd 76, Hammondsport, NY 14840
Phone: (607) 868-4100
Website: https://klvineyards.com/
On the way home or for an alternate locale to check out, go to Krooked Tusker Distillery for Fire Pit Friday. From 6-8pm, join your friends (and make new friends) around the fire with cocktails, food, cigars and s’mores. An adult campfire sounds nice with an Apple Butter Chai Martini in hand (a must try for a seasonal cocktail by Krooked Tusker!).
Krooked Tusker Distillery is a craft distillery known for creating unique, small-batch spirits with a distinctive local character. Located in the Finger Lakes region, it offers visitors a welcoming place to sample handcrafted drinks and enjoy the area’s vibrant craft beverage scene.
Location: 10303 Co Rd 76, Hammondsport, NY 14840
Phone: (607) 868-3006
Website: https://www.krookedtusker.com/
Are you visiting Keuka Lake? Stay on the lake this holiday weekend. With the season changing to fall, a lot of lake rentals don’t require the week rental length. Find a dreamy stay for the long weekend with Finger Lakes Premier Properties.
Finger Lakes Premier Properties offers vacation rentals and real estate services throughout the beautiful Finger Lakes region of New York. With a variety of properties in scenic lakefront and countryside locations, it helps guests and homeowners make the most of their time in the area.
Location: 103 Horizon Pk Dr, Penn Yan, NY 14527
Phone: (844) 741-8022
The Small Town Saturday Stroll Itinerary
Begin with Breakfast
A day on Main Street should begin with a home style breakfast at Angel’s Family Restaurant. With morning delights to savor over, grab a stool at the counter or a booth for the family, and fill up for a morning stroll.
Angel’s Family Restaurant is a beloved, old-fashioned diner in downtown Penn Yan, known for hearty breakfasts, classic comfort food, generous portions, and friendly service. With its nostalgic atmosphere and welcoming, hometown feel, Angel’s is a favorite spot for both locals and visitors looking for a relaxed meal in the heart of the Finger Lakes.
Location: 5 Main St Apt 2, Penn Yan, NY 14527
Phone: 315-536-4026
Shop Main
Starting at the south end of the street head north and shop until you drop. With over 20 storefronts on Main Street your eyes will be delighted with fall window shopping, gifts and souvenirs, and lovely hand crafted items from local artists and shop owners.
Participate in the Arts at the Arts Center of Yates County, view the current exhibit and shop their collection of art and jewelry made by Local Artisans. Get nostalgic and have a sweet sugar rush at the Keuka Candy Emporium, located in the historic Lown’s Building that once housed Lown’s Dry Goods and Department Store for 122 years. Adore the brick facades, take a photo with the Birkett Mills Pancake Griddle, and gasp at the colorful fall reflections from the bridge over the outlet. But don’t stop there! Pick up a handmade soap at Judd’s Suds. Ladies, shop at Simplicity on Main for a fall wardrobe update. Pursue antiques at 2nd Hand Treasures & Antiques. Sip on a coffee at Amity Coffee Co. or on a smoothie at Milly’s Market & Cafe. Dive into the local bookstore and find everything from gifts to supplies at Long’s Cards & Books. Phew. And that’s just a sample of the Main Street Shops!
Stories of Main and Penn Yan
As the business district seems to end on the north side of Main, don’t stop - instead continue your stroll to Chapel Street. At the corner sits the Oliver House and the Yates County History Center. Stroll the museum buildings and learn a little local history. Dive into the exhibits and be amazed on the historic influence and connections Penn Yan and Yates County had in the past.
But the history fun doesn’t have to stop there. On your way out purchase the Audio Tour and the accompanying map of the Village for a fascinating history tour. You’ll hear about the buildings and selected stories of Main Street’s past. As you stroll back down Main , scan the QR codes on the map to hear the short audio segments and get in a little historic knowledge that might just foreshadow a spooky tale you’ll hear later in the evening! (Keep reading if you haven’t guessed yet what I mean by that!)
Early Afternoon
With a sip, savor, and shop well underway, as well as a stroll down history lane, it is time to a to stock the fridge for your lake house stay. The place to go for the quintessential small town, local grocer experience is Morgan’s Grocery. This family owned and operated grocer has a full service meat counter/butcher, local produce, groceries, home essentials, beverages including beer, and baked goods! Oh. The. Baked. Goods. Trust me, don’t resist getting a locally baked pie or a mini-cheesecake dessert for one at check out.
Morgan’s Grocery in Penn Yan, NY, is a convenient local market offering a variety of everyday groceries and essentials. It’s a friendly neighborhood stop for residents and visitors looking to pick up fresh food, household items, and other necessities.
Location: 100 Hamilton St, Penn Yan, NY 14527
Phone: (315) 536-6612
Website: https://morgansgrocery.com/
Enjoy the early evening by the lake, grill the T-Bone from Morgan’s and have a slice of pie. Unwind and relax, but only just a little. We have one more stop for the evening.
Spooktacular Tales & Local Lore
Step into the shadows of Penn Yan’s past with Murder and Mayhem at the Yates County History Center, where history takes a darker and more mysterious turn. Hear chilling tales of unsolved crimes, shocking scandals, suspicious deaths, and the real-life characters who left their mark on Yates County.
The immersive storytelling tours are every 30 mins and begin at 6pm. Pre-sale only for tickets, call (315) 536-7318 or stop in at the History Center before Saturday to reserve you spot.
The Yates County History Center in Penn Yan, NY, preserves and shares the rich history of Yates County through historic collections, exhibits, programs, and community events. From local stories and family histories to fascinating glimpses into life in the Finger Lakes, the center offers visitors a chance to connect with the people and places that shaped the region.
Location: 107 Chapel Street Penn Yan, NY 14527
Phone: (315) 536-7318
Website: http://www.yatespast.org
Night Cap on the Canal
It’s been a busy day, but I think you may need a night cap to sip away those spooky chills that keep lingering.
Head to Outlet 111, the hottest and most elegant cocktail bar in the area, for a hand crafted drink to sip away any fright that still lingers. The water views of the Outlet and the modern interiors seem to transport you back to the current era and help you unwind and seemingly forget those haunted tales you just heard for a good night’s sleep.
Outlet 111 is a waterfront cocktail and charcuterie bar located on the Keuka Outlet. Offering outdoor seasonal seating, live music, and special ticketed events.
Location: 111 Liberty St, Penn Yan, NY 14527
Phone: (315) 694-7028
Sunday Fall in Love with Autumn
Rise at Your Will (it’s Sunday after all) & Shine Lake Side
While staying at the lake, begin your Sunday with a home cooked breakfast and a lake view, your soul and stomach will be fulfilled for a day of adventure. If cooking isn’t your style or your view is not the lake, catch Sunday Brunch at the Main Deck. Located on Keuka Lake, enjoy the views with a sophisticated plate and a spirit-free cocktail suited for fall flavors.
Main Deck in Penn Yan is a lakefront dining destination overlooking beautiful Keuka Lake, offering brunch, lunch, and dinner with a menu that blends contemporary American cuisine, seafood, farm-to-table dishes, burgers, and vegetarian and vegan options. Guests can also enjoy craft beers, wines, creative cocktails, live entertainment, and the casual lakeside atmosphere of the Tunnel Bar, making Main Deck a versatile spot for everything from a relaxed meal to an evening out.
Location: 301 Lake St, Penn Yan, NY 14527
Phone: (315) 694-7536
Website: https://www.maindeckpy.com/
Seize the Spectacular Scenery
With Brunch complete, its time to take a scenic drive through the hills and around Canandaigua Lake to Bristol Mountain for their Annual Fall Festival.
The Fall Festival at Bristol Mountain is a fun-filled autumn celebration featuring beautiful foliage, scenic mountain views, local vendors, food, and live entertainment. Ride the popular Fall Sky Ride for breathtaking views of the Finger Lakes and the surrounding hills. At the top of the mountain hop off and enjoy the special festivities and the Summit Live Music Stage. Spend some time up high, take a summit hike, and then return to the base on the Sky Ride for additional live music, a variety of food trucks, shops the 25+ vendors, and more! For the adventurous check out the additional admission experiences including the Aerial Adventure Park, Rock Wall and Bungee Trampolines, The Launch, and the Kids Adventure Park.
Purchase your tickets in advance, there is limited admission available each day: https://www.bristolmountain.com/fall-festival/
Bristol Mountain Fall Festival
When: Saturday October 10th & Sunday October 11th
Time: 11am - 5pm
Location: 5662 NY-64, Canandaigua, NY 14424
Phone: (585) 374-6000
Website: https://www.bristolmountain.com/
The festival is the perfect way to spend a day in the fall amongst the natural beauty and festive spirit of the Finger Lakes. Sip, savor and shop your day at Bristol Mountain Fall Festival.
Reflect with Fire
As Sunday winds down and after all that fresh air, wind your way back home for the evening. Adorn your flannel, open the bottle of wine you bought today (you did buy a bottle, or two, right?), light a campfire, and enjoy the crackle of a fall fire lakeside. Reflect in the flames the fun, the mystery, the miles, and the memories made this weekend. And plan your next adventure to the Finger Lakes!
Why We Love Fall in Penn Yan
In the fall, the Finger Lakes is known for its unmistakable golden glow. The autumn leaves in yellows and golds, the reflections are still on the lake. The skies at dusk are colorful and the shop storefronts glow with light. The moon is full and bright, the air is crisp and cold. Wine is warm, flavors are bold.
That is October in the Finger Lakes.
Weekly Events List
10am • Acrylic Painting 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
4pm • Come Over October: Tapas & Wine Experience • Fox Run Vineyards
5-8pm • Open Mic Night • Keg & Barrel
6-8pm • Music Wednesday with Tink Bennett • Lake Life Brewery
6-8pm • Name That Tune Bingo • Outlet 111
10am-5pm • Pretzel & Wine Pairing • Fulkerson Winery
10am-5pm • Wine & Pickle Pairing • Toast Winery
11am • Food & Wine Experience: Fall Series (Reservations Req'd) • Fox Run Vineyards
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
4-7pm • Live Music Friday with Pat Harrington & Owen Eichensehr • Weis Vineyards
4-7pm • Live Music with Madelyn Rose • Keuka Brewing
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 Dave Peterson & Foodtruck by Rays' Mobile Food • Keuka Lake Vineyards
6-8pm • Fire Pit Friday Nights - Food, Music, Cigars & S'mores • Krooked Tusker Distillery
8am-4:30pm • Fall Fest & Farmer’s Market & More • The Windmill Farm & Craft Market
9am • Saturday Yoga • Hunt Country Vineyards
10am • Guided Wine Tour • Lakewood Vineyards
10am • Gelli Plate Printing with Ginny Deneka • Arts Center of Yates County
10am-3pm • Chicken BBQ • Oak Hill
10am-5pm • Pretzel & Wine Pairing • Fulkerson Winery
10am-5pm • Wine & Pickle Pairing • Toast Winery
11am-4:30pm • Tabora Cookie & Wine Pairings • Tabora Farm & Winery
11am-5pm • Fall Festival (Tickets Req'd, Admission is Limited) • Bristol Mountain
Noon-2pm • Live Music with Logan Route • The Windmill Farm & Craft Market
1-6pm • Food Truck by JR's Back Alley BBQ • Krooked Tusker Distillery
2-5pm • Fall Fest at the Farm • Lincoln Hill Farms
3-6pm • Live Music with Rusty Strings • Blue Eagle Tavern
3-6pm • Live Music with Black Robin Band • Krooked Tusker Distillery
4-7pm • Live Music with Unparallel Band • Black Sheep Distillery
5-8pm • Farm Dinner Series • Dean Lane Dining
5-8pm • Live Music with Payton Clark • Laurentide Brewing Company
6pm • Murder & Mayhem (Advance Tickets Req'd) • Oliver House at the Yates County History Center
6-10pm • Halloween Fest (Every Saturday in October) • Lincoln Hill Farms
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
11am-5pm • Fall Festival (Tickets Req'd, Admission is Limited) • Bristol Mountain
Noon-4pm • Bloody Mary Bar • Krooked Tusker Distillery
12:30-3pm • Live Music by Madelyn Rose • Once Finger Lakes
1pm • Guided Wine Tour • Lakewood Vineyards
1-5pm • Food Truck by JR's Back Alley BBQ • Krooked Tusker Distillery
2-5pm • Live Music with Jay - Acoustic • Krooked Tusker Distillery
1-6pm • The British Sunday Roast & Brit Car Sunday Social • Seneca Lake Brewing Company
Thank you for reading another issue of Water & Wine Weekly! Take in the changing colors and crisp air this weekend, see you out there!
Claudia
Curating your experience in Penn Yan, New York
