Water & Wine Weekly • Penn Yan, New York • October 19-25, 2026 • Issue 21
Halloween is upon us and Penn Yan is a hot spot for family fun, spooky stories, and an abundance of candy this weekend. Adorn a costume and have a little halloween fun this weekend at Wager’s Halloween Glow Maze and Downtown’s Trunk or Treat!
Burn off the sugar high (and the extra calories from the sweet treats) with an autumn hike. The Finger Lakes area is nearing our Autumn Leaf Peak, don’t miss the fantastic colors and lake views this fall!
But before you head out there, read all about…
Gather the Family and Glow
Wager’s Cider Mill has long been a favorite stop for apple lovers, fresh cider, and those irresistible apple cider donuts. Now, with its growing lineup of fall activities, it's a wonderful place to make even more seasonal memories.
Head to Wager’s Cider Mill Maze to celebrate the season. (Read more here…)
What: Glow Maze • Where: Located just a mile up the road from @wagerscidermill on Hoyt Rd in Penn Yan, New York • When: Friday October 23, 2026 from 7-9pm
Celebrate Halloween with a Trunk or Treat Tradition in Penn Yan
Get ready for a little Halloween magic in downtown Penn Yan! If you’re looking for a fun, family-friendly way to celebrate the spooky season in the Finger Lakes, mark your calendar for Trunk or Treat on Main Street in Penn Yan. This annual community favorite brings costumes, candy, music, and plenty of Halloween spirit to the heart of Penn Yan!
On Saturday, October 24, 2026, from 4:00 PM to 6:00 PM, Main Street will transform into a festive Halloween gathering where little ghosts, superheroes, princesses, and other (read more here…)
What: Trunk or Treat • Where: Main Street, Penn Yan • When: Saturday, October 24, 2026 from 4-6pm
Autumn Views
The air is crips, the sun is bright this weekend. Head to the State Park!
Dog friendly, kid friendly, and just what everyone needs in fall… a hike in the wood. Let the leaves crunch and take in the lake views. Get outdoors and enjoy the fall air.
What: Fall Hiking • Where: Keuka State Park • When: Open Daily from Dawn to Dusk
Your Curated Weekend Itinerary
Start your Friday by exploring downtown Penn Yan, where you can browse local shops, grab a bite to eat, and enjoy the charm of this lakeside village.
Sip a deep red to kick off a fall evening at the Burnt Rose Wine Bar and Savor the Homemade Mac and Cheese at the Keuka Restaurant. Head up Main Street to Shop at Wager’s Cider Mill for a seasonal treat, try a cider donut or take home an apple pie. Then head to the CornMaze to celebrate the season with a Glow. A perfect Friday in Penn Yan.
Saturday costumes are encouraged for an afternoon of family fun. Begin with a Saturday stroll around downtown, discover local shops, restaurants, and welcoming spots to grab a bite to eat. Whether you're craving a casual meal, a sweet treat, or a warm drink on a crisp October afternoon, Penn Yan is a lovely place to spend time with family and friends. Then celebrate Halloween, local businesses, and organizations at the Trunk or Treat on Main Street in Downtown Penn Yan. Whether for viewing the decorated trunks or the treats, the event is fun for all ages!
The Trunk or Treat celebration begins at 4pm and will feature a costume parade, a decorated trunk competition, games, food trucks, and more. It's a great opportunity to let the kids burn off some energy, snap a few adorable costume photos, and make memories together.
Sunday is all about autumn and lake views. Hit the road and make your first stop the Black Cat Bistro. A favorite amongst lake cottagers in the summer, in the fall hours are limited to Saturday and Sundays. Sip on a local roasted cup of java, Savor a seasonal pastry, and Shop Keuka inspired gifts all at Black Cat Bistro. With your body and soul fueled up, head south to hike Keuka Lake State Park.
Keuka Lake State Park is open dawn to dusk in the off season and currently has no state park entry fee. Before you head out, grab a trail map and my recommendation is to park at Camp Sites to hike down to Keuka Lake.
Once in the woods, allow your body to relax. The leaves are bright and crisp. The air is quiet. The fall aroma of earth hits your nose. Spot a chipmunk sitting on a tree stump or watch in awe the blue herring glide along the glistening lake.
Autumn hikes are all about taking it all in, using all your senses, it simply lifts your soul. Hike Keuka Lake State Park this weekend. I think you’ll find yourself back again and again.
From glowing fall festivities and apple orchards to local restaurants, wineries, and scenic drives around Keuka Lake, there's always something new to discover in the Finger Lakes.
Weekly Events List
10am-5pm • Pretzel & Wine Pairing • Fulkerson Winery
11am • Food & Wine Experience: Fall Series (Reservations Req'd) • Fox Run Vineyards
11am-4:30pm • Tabora Cookie & Wine Pairings • Tabora Farm & Winery
3pm • Open Doors: Farm Tour • Hermann J. Wiemer Vineyard
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 Miranda Sickler & Foodtruck by Ray's Mobile Food • Keuka Lake Vineyards
6-8pm • Fire Pit Friday Nights - Food, Music, Cigars & S'mores • Krooked Tusker Distillery
6-8pm • FLX Trivia • Lyonsmith Brewing Company
7-9pm • Halloween Glow Maze • Wager’s Cider Mill
8am-4:30pm • Farmer’s Market & More • The Windmill Farm & Craft Market
9am • Saturday Yoga • Hunt Country Vineyards
10am • Guided Wine Tour • Lakewood Vineyards
10:00am • Creating a Bouquet of Flowers with Toni Johnson • Arts Center of Yates County
10am-5pm • Pretzel & Wine Pairing • Fulkerson Winery
11am-4pm • Fall Sky Rides • Bristol Mountain Ski Resort
11am-4:30pm • Tabora Cookie & Wine Pairings • Tabora Farm & Winery
3-6pm • Live Music with Live Munkey • Krooked Tusker Distillery
4-6pm • Trunk or Treat • Main Street Penn Yan
5-8pm • Farm Dinner Series • Dean Lane Dining
5-8pm • Live Music with States Apart • Laurentide Brewing Company
6-9pm • Halloween Fest (Every Saturday in October) • Lincoln Hill Farms
10am-5pm • Sparkling Sundays • Glenora Wine Cellars
10am-5pm • Pretzel & Wine Pairing • Fulkerson Winery
11am-3pm • Boozy Coffee Flights • Krookid Leyk Distilling
11am-3pm • Sunday Brunch • Castle Grisch
11am-4pm • Fall Sky Rides • Bristol Mountain Ski Resort
11am-4:30pm • Tabora Cookie & Wine Pairings • Tabora Farm & Winery
Noon-4pm • Bloody Mary Bar • Krooked Tusker Distillery
1pm • Guided Wine Tour • Lakewood Vineyards
1-6pm • The British Sunday Roast & Brit Car Sunday Social • Seneca Lake Brewing Company
2-5pm • Live Music with PJ Elliot • Krooked Tusker Distillery
5:30-8:30pm • Haunted Stroll • Sonnenberg Gardens, Canandaigua
Thank you for reading another issue of Water & Wine Weekly! I hope you have an awesome autumn weekend!
Claudia
Curating your experience in Penn Yan, New York
