Follow the Delaware River north, past the Jersey border, past the Poconos and the Water Gap, and in about three hours, you’ll arrive in Callicoon, at the foot of New York’s Catskill Mountains.
The region has been an iconic American resort destination since the late 19th century, most famously during its Borscht Belt heyday, when Jewish families filled sprawling summer resorts to play tennis, lounge by the pool, and stir up trouble with dirty dancers. Riding the popularity of the neighboring Hudson Valley, the Catskills’ recent revival offers easy access to nature without requiring you to rough it. Think vintage shopping, natural wine, and cedar saunas between snowy walks through the woods.
The Catskills are huge (about 6,000 square miles), so for the purposes of this getaway, you’ll focus on the Western Catskills, which rise from the Delaware River and are less rugged than their eastern counterparts. Nothing on this itinerary is more than 30 minutes apart. Start the car.
Stay: Kenoza Hall
There are more than a dozen cool places to stay in the Western Catskills, four of which come from locals Kirsten Harlow Foster and Sims Foster of Foster Supply Hospitality. Their properties blend the idiosyncratic architecture and fine craftsmanship of historical buildings with the luxury finishes and playful amenities you want on a weekend escape.
At Kenoza Hall, perched above the lake of the same name, rooms are split between the Victorian inn and a cluster of cottages with front porches, gas stoves, and arched armoires. Inside, there are plenty of cozy corners for reading or cocktails as snow falls outside. Don’t miss the spa, with its pebble-floored relaxation room and cedar barrel sauna.
📍 5762 Route 52, Kenoza Lake, N.Y. 12750
Shop: Downtown Callicoon
Hugging the New York side of the Delaware River, the riverside village of Callicoon has evolved from its past lives (hunting grounds, timber town) into an artsy retail refuge for Catskills visitors. Browse groovy lamps at Callicoon Vintage, elevated tableware at Spruce Home Goods, hand-dyed yarn at Wool Worth, and more at the new and old boutiques along Lower Main Street. Tucked behind Callicoon Caffé, at the Shell gas station of all places, is an excellent photo op: the Callicoon Bridge spanning the Delaware.
📍 Lower Main Street, Callicoon, N.Y. 12723
Eat: Annie’s Ruff Cut
Rightly famous for its roast beef, Annie’s Ruff Cut in nearby Cochecton might consider a name change to Annie’s Exquisitely Cut. The beef is sliced paper-thin, piled high in cold sandwiches or served open-faced and drenched in warm gravy. The vibe is classic country tavern: old wood, beer swag, and locals mildly surprised you found the place.
📍 90 Forman Rd., Cochecton, N.Y. 12726
Snack: North Branch Cider Mill
Warm apple cider, cinnamony cider doughnuts, and the smell of a smoldering wood stove pull you into North Branch Cider Mill, a rust-red outpost along the North Branch Callicoon Creek. This historic operation has been around since 1942 (and under new ownership since 2022) and while they’re not pressing their own apples yet, it makes an atmospheric stop for a snack and shop along the old-timey general store-style shelves: New York maple syrup, sweet dill pickles, candles, ceramics, and more.
📍 38 N. Branch Callicoon Center Rd., North Branch, N.Y. 12766
Watch: Callicoon Theater
A block off Callicoon’s main commercial drag, the Callicoon Theater hides a 35-seat, barrel-ceilinged auditorium behind its art deco façade. Catching a first-run movie here is worth it for the architecture alone. Dating to 1948, it’s the oldest movie theater in Sullivan County.
📍 30 Upper Main St., Callicoon, N.Y. 12723
View: Catskills Art Space
Though the Catskills cachet is a relatively recent phenomenon, its status as an arts haven goes back decades, with the founding of Catskills Art Space in 1971. Housed in a converted theater in the cute downtown of Livingston Manor, half an hour northeast of Callicoon, since 2007, the dynamic gallery features a mix of up-and-comers and heavy hitters — Sol LeWitt and James Turrell both have site-specific exhibits here through 2027.
📍 48 Main St., Livingston Manor, N.Y. 12758
Dine: The DeBruce
Another stylish Foster Supply property, the DeBruce sits in the scenic Willowemoc Valley, about 10 minutes east of downtown Livingston Manor. You could stay here — original wood doors and claw-foot tubs make a compelling case — but the award-winning tasting menu is the real draw. In the tranquil, forest-view dining room, bergamot scents a matsutake raviolo, and coal-baked pears meet scallops and parsnips. Cross the storybook bridge over the Willowemoc River to arrive, and if you have time, explore the five miles of trails that wind through the woods behind the property before dinner.
📍 982 DeBruce Rd., Livingston Manor, N.Y. 12758
