What to Do in Tannersville: A 24-Hour Guide to the Upstate Town

The Greene County village is a must for retro eats, vintage shopping, and a heap of Hudson Valley history in the Catskills.

There’s something otherworldly about Tannersville. Otherwise known as “The Painted Village in the Sky,” the Greene County town draws in visitors with landscapes that resemble something out of a Thomas Cole painting. With outdoor entertainment ranging from snowshoeing and ice-fishing to hiking, biking, and camping, the area is a dream for Hudson Valley adventurers. Of course, it’s quite the hidden gem for antique hunters and foodies as well, thanks to its surprising slew of historic restaurants and shops in town.

Intrigued? You should be. Take a browse through our day trip guide, then get planning your own venture to the village.

9 a.m. Savor breakfast at Bear and Fox Provisions

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Start your day at this cozy cafe on Main Street where you’ll find freshly baked goodies, hearty sandwiches, and steaming coffee. Bear and Fox Provisions is all about pre-ski caffeine boosts and post-hike relaxation, and the warm and inviting spot also has gifts to shop on your way out like Catskills-themed gear, greeting cards, and artisanal mugs and candles.

5932 Main St, Tannersville

10:30 a.m. Shop for antiques and art on Main Street

Recent years have seen a substantial revitalization on Main Street, with The Hunter Foundation refurbishing buildings now occupied by a good many antiques businesses and art galleries. Tannersville Antiques is a historic building piled to the rafters with vintage finds, making it the largest antiques shop in the greater Catskills area, while Rustic Mountain is a home goods store that specializes in hickory furniture and other vintage décor items. Come prepared with reusable bags in hand and comfortable shoes on your feet for a fun morning popping from one shop to the next.

11:30 a.m. Pick up something sweet at Shandaken Bake


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This relatively new bakery is now a staple in Tannersville, serving up pastries, pies, tarts, cakes, and tea snacks on the weekends. Stop in to browse Shandaken Bake’s beautiful display case packed with mini key lime pies, raspberry shortbread cookies, and savory biscuits before picking the perfect treat to keep you fueled through mid-morning.

6036 Main St, Tannersville

12:30 p.m. Munch on lunch at Mama’s Boy Burgers

This vintage location serves high-class versions of your typical fast food burgers, with great vegetarian options and custard milkshakes that might remind you of Shake Shack. With an outdoor window, this is a great to-go option in summer for when you want to see more of the Western Catskills, and the perfect place to grab a hearty bite to warm up in the colder months.

6067 Main St, Tannersville

1:30 p.m. Take a hike in the mountains


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Tannersville sits toward the center of one of the greatest areas for outdoor activities in the Northeast. Experienced hikers can scale the Devil’s Path, which is regarded as one of the most challenging hikes on the east coast, and serious work has been done to make the Tannersville-Hathaway trail system better for mountain bikers. For those looking for a slightly simpler stroll, we recommend the Escarpment Trail to Kaaterskill Falls, which is a 2.3-mile out-and-back trail just outside of town that might end with some muddy shoes but will definitely have great views.

4:30 p.m. Head to happy hour at Slopes Bar & Restaurant

Before sitting down for dinner in town, check out Slopes for a refreshing drink after a long day. The après ski-centered bar and restaurant welcomes skiers and snowboarders from Hunter Mountain, as well as sports fans who are trying to catch the game with a pint. Play a round of pool with an ice-cold IPA in hand, or hang out at the bar with a margarita, even if it’s not quite five o’clock yet.

6002 Main St, Tannersville

6:30 p.m. – Enjoy food and live music at Last Chance


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The oldest restaurant in town is going strong these days, with a massive tavern space that serves hundreds of beers and whiskeys as well as a locally-derived menu of American staples, with plentiful gluten-free and vegetarian options. It hosts music on weekends year-round, with a mixture of country and Americana as well as jazz, indie rock, and more experimental sounds that might make you want to grab a couple drinks and sit awhile.

6009 Main St, Tannersville

9:30 p.m. – Rest your eyes at Hotel Mountain Brook

This high-class place was refurbished with help from the Hunter Foundation, which transformed the 1940s motel into a wood-paneled Adirondack-style lodge. Its fully appointed rooms with antiques, fireplaces, and views start at $189, with private king-size cabins from $349. Full breakfast is included with every room.

57 Rd 23C, Tannersville

Related: What to Do in Windham: A 24-Hour Guide to the Greene County Retreat

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