The Catskill Mountains region, two hours north of New York City and west of the Hudson River, has long been a getaway for urban dwellers. It inspired landscape painters from the Hudson River School artists in the mid-1800s, and as the 20th century dawned, it became a refuge from crowded New York City. The sanitariums later gave rise to lavish resorts that became known as the “Borscht Belt.”
Now, young folks and families show up for a vacation and decide to stay for the quality of life. People see opportunity in working-class and post-hippie enclaves like Woodstock. This has helped to spark fresh ideas in food, hospitality and wine.
Some of the area’s best eating and drinking occurs at a new breed of design-friendly motels, hotels and inns set along dark country roads nestled in small towns. Here’s an overview of where to drink wine, beer and cider around the Catskills.
Livingston Manor is the birthplace of American fly-fishing. Despite its popularity with outdoor sports fans, the Upper Delaware Valley area of the Catskills suffered decades of economic decay.
Today, the area is in the midst of a mini-boom in tourism, thanks in part to Kirsten Harlow Foster and her husband, Sims Foster, co-founders of Foster Supply Hospitality. With roots in Livingston, they left New York City to reimagine historic buildings as inns and restaurants. The couple’s current portfolio is comprised of The Arnold House and The DeBruce in Livingston Manor, The North Branch Inn in North Branch and Nine River Road in Callicoon. They also have additional projects in development.
Of these, The DeBruce is true destination dining. A room at the creekside hotel scores guests a table in its glass-walled dining room. Executive Chef Aksel Theilkuhl’s nine-course seasonal menu, complete with wine pairings, is one of the finest experiences of hyperlocal food in the Catskills.
Just beyond downtown Livingston Manor, the tavern at The Arnold House pours Finger Lakes wines like Dr. Konstantin Frank alongside Old World classics. The North Branch Inn, one village over, rotates through mostly American stock that includes great value Gruet Brut from New Mexico by the glass.
A small community west of Livingston Manor, Roscoe harbors The Red Rose Motel & Tavern. Rooms incorporate reclaimed wooden beds and vintage collegiate touches like pennants emblazoned with “Catskills Mts.” The adjacent tavern stocks local ciders and New York wine.
Continue about 20 minutes west to Eminence Road Farm Winery. The small winemaking team works out of a converted cow barn, and it uses natural winemaking methods on sustainably farmed vinifera grapes sourced from the Finger Lakes region. Tastings are by appointment.
To the northeast lies Andes, a quiet town applauded for its cute main street and antique shops. But the latest reason to visit is Wayside Cider. Alex Wilson keeps one foot in NYC, though he spends more time here now that his artisan cidery, set in a restored barn, has become more popular. Along with dishes liked smoked trout, lamb chili and lamb kebabs, Wayside serves local craft beers and regional wines.
If you stay overnight, book a dinner at Brushland Eating House. The owners, Brooklyn transplants, have received international press for Brushland’s farm fare. The wine list pulls from the Catskills’ own Eminence Road to far-flung Sardinia and the Canary Islands. If you need something offbeat to bring back to your room, stop at their Delhi wine shop Dixie’s.
Skiers and snowboarders know the Northeast for winter sports. At Hunter Mountain, Scribner’s Catskill Lodge offers a modern vibe. The restaurant Prospect excels at tender handmade pastas, Hudson Valley beef and seasonal vegetables served with New York and international wines.
Hunter Mountain doesn’t have a town per se, so nearby Tannersville serves the role. Hudson-Chatham Winery has a tasting room with local cheeses, charcuterie and tapas. Owners Carlo and Dominique DeVito is one of the biggest proponents of wine made with vinifera and hybrid grapes like Baco Noir.
Just south of the mountain, tucked into a one-way in, one-way-out valley is the Spruceton Inn. A Brooklyn couple escaped to the woods to restore a dilapidated motel, begins the premise. Guests come for hiking, weak cell towers and to shoot the breeze over a glass of Pot de Vin wine at the bar, or across the street at West Kill Brewing.
Perhaps the most famous town along the eastern fringes of the Catskills is Woodstock. Originally an artist colony, it later became a haven for musicians and hippies. Now, young and middle-aged searchers arrive to practice art, yoga and launch hotels and restaurants.
SILVIA has filled that latter niche. With its sharp exterior painted classic black, chef Doris Choi and husband Niall Grant prepare refined seasonal fare out of a wood-fired grill with a Korean twist. The cozy bar pours great cocktails alongside a natural-leaning, small-producer wine program.
The newest spot for wine in town, Early Terrible offers moody vintage ambience set inside a rustic wooden barn, which creates a steampunk-in-the-woods vibe. During the day, the adjacent structure up the hill, The Mud Club, sells wood-fired Montreal bagels and pulls the best espresso in town.
In 2016, cicerone Megan Reynolds opened R&R Taproom on the edge of town. But her passion for funky wild American sours led her to the raw wine movement. The result: the first place for natural wine in Woodstock. Her list, a work in progress, has a dozen selections and recently included a Grüner Veltliner from Austrian biodynamic producer Jurtschitsch and a Sardinian Vermentino. Each wine provides an easy foray into natural wine for those new to the category.
Known for its ambitious cocktail program, A&P Bar’s wine list stands out for selections like Klein Constantia’s Sauvignon Blanc from South Africa. The three-level restaurant, which was formerly an A&P grocery store, also offers a full menu of comfort food.
The new Woodstock Way Hotel blends sustainable design with the village’s musical legacy. Bob Dylan once holed up not far from its doors. The front desk can provide schedules for concerts and shows, but that’s if guests can pull themselves away from record players in their minimalist rooms.
Head to the outdoorsy community of Phoenicia. The small town, popular with tourists for tubing along the Esopus Creek, is a mixed haunt of bikers, Brooklynites and fly fishers. Woodstock Brewing does serve wine, but its owners have a soft spot for local cider and offer a rotation of beers with names like Alpha Particle and Context & Memory, alongside their standard brews.
In the same area, The Pines, open Thursday to Sunday, offers brunch by day and a tightly edited wine list and dinner menu by night. Live music on the weekend and a couple of simple, breezy guestrooms keep the buzz going at the bar well after dinner.
Though not technically in the Catskills, this historic Hudson River town is considered a gateway to the region. The main bus line for commuters and weekenders, Trailways, connects visitors with locations west from Kingston. The town is light on lodging, but the Forsyth B&B is the most contemporary choice with rooms that blend vintage pieces and modern design.
For dinner, Boitson’s has a pleasant patio to explore its all-tap wine list. Nearby, the garden-to-table Wilde Beest, which opened last summer, boasts the town’s most exciting wine program. Selections skew heavily toward sustainable, organic and biodynamic producers.
Don’t miss an afternoon glass of wine, cider or beer at Rough Draft. An all-day brews and books spot that includes pour-over coffees, it sits on Kingston’s famous four corners. It’s the only intersection in America where all four intact buildings were built pre-Revolutionary War.
Finally, Brunette was the first wine bar and natural program in Kingston. Imbued with a charming Parisian ambiance, owners pour what they like to drink, which happens to be minimal-intervention wines.
Down the block, Kingston Wine Co. is the go-to bottle shop, whether you need cloudy and funky or fined and filtered classics. Its stock includes lots of local labels, wines in cans and biodynamic stuff from France.
Last Updated: May 5, 2023