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.

Adobe Stock | Photo by Louis Dallara

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 entertainments 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. Tag us @HudsonValleyMag on Instagram if you visit!

- Advertisement -

9 a.m. – Savor breakfast at Maggie’s Krooked Café

Maggie’s has been a local staple for more than 30 years, and her organic breakfasts are as creative (and as healthy) as you’ll find in the area. Garden-fresh omelets, prodigious pancakes, and a tofu scramble for vegetarians make this a perfect place to fuel up for a long day. Maggie herself is a fantastic source of information and can give you any tip you’re looking for.

6000 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. The Antique Annex and Tannersville Antiques are historic buildings piled to the rafters with vintage finds, while Say What is a reliably interesting gallery. Come prepared with reusable bags in hand and comfortable shoes on your feet for a fun morning popping from one shop to the next.

- Partner Content -

11:30 a.m. – Pick up coffee and donuts at Twin Peaks

Continue down Main Street until you hit one the best recent additions to town. Opened in 2014 by two local couples, Twin Peaks serves up house-roasted coffee and fresh-made donuts in a comfy, unpretentious location. Choose creative flavors like Samoa (like the cookie) or Key Lime Pie, or even just the classics (cinnamon sugar is a favorite), and then watch them made in front of you on the Donut Robot. Save room.

5950 Main St, Tannersville

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

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.

6067 Main St, Tannersville


View this post on Instagram


A post shared by Marcus Robinson (@epicblu)

- Advertisement -

1:30 p.m. – Take a hike (Rip Van Winkle Lake or Huckleberry Ledge)

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, and serious work has been done to make the Tannersville-Hathaway trail system better for mountain bikers. For those looking for slightly simpler strolls, we recommend the newly refurbished Rip Van Winkle Lake or the muddier but more rewarding Huckleberry Ledge, which overlooks the Platteclove and one of the woolliest drives in the Catskills.

4:30 p.m. – Have a wine tasting at Hudson-Chatham Winery in Tannersville

Cool off in the summer or warm up in the winter with a tasting at this community favorite spot on Main Street. This outpost of Hudson-Chatham Winery hosts special holiday deals (for Valentine’s Day, expect a pairing of Hudson Valley chocolates with ideal wines) and stock vintages both local and international.

6036 Main St, Tannersville

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

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 in Tannersville

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 $150, with private king-size cabins from $300. Full breakfast is included with every room.

57 Rd 23C, Tannersville

Related: How to Spend 24 Hours in Piermont

Our Digital Partners

Learn how to become a digital partner ...

The Big Sip, the Hudson Valley's premier wine and spirits fest, is October 7-8!