In his 1918 travelogue The Catskills, author T. Morris Longstreth characterized the mountainous region as a place “meant for those who will look twice.” It’s an apt description of Callicoon, a small town along the old Borscht Belt—a once-bustling vacation area that at its height was home to 500-plus hotels. One of dozens of unassuming yet growing north-of-Manhattan towns that look similar on the surface, Callicoon offers a wealth of opportunities for deeper exploration.
Where to stay
So new it’s not even on Google Maps, the Boarding House lies at the edge of Route 97, overlooking the hamlet of Callicoon. This is the “downtown” portion of the eponymous town (population about 3,000), and you’d be forgiven for thinking you’ve stepped onto the set of an Industrial-era movie. An old hospital and its next-door nurses’ quarters have been transformed into a luxury hotel rooted in the tradition of the railroad boarding house, which was designed to feel like a cozy, inviting home away from home.
The interiors, designed by Homestedt, known for the Livingston Manor Fly Fishing Club, are inspired by the simplicity and clean lines of Shaker design. Functional and balanced, with lots of natural materials, neutral colors, and furniture sourced from regional antique shops, the Boarding House feels warm, lived-in, and serene.
The hotel has a total of 8 apartments and 17 bedrooms. (For now, only apartments are available for rent. The two third-floor apartments have a single bedroom apiece, so they function as individual suites.) Each apartment has a seating area, an efficiency kitchen, and a bathroom.
Some bedrooms have vintage clawfoot tubs set under a window or a skylight, for a sun- or moonlit soak. They also have plush mattresses topped with hand-sewn linen sheets and down pillows.
What you won’t find in these rooms? A single TV. That’s a good thing.
On the ground floor, there’s a relaxed shared living room, library nook, and porch. The basement contains a large communal kitchen, similar to those found in English country homes. Cook a meal on the vintage Elmira cookstove, and serve it family-style on the solid oak table—made from a tree felled at sister property Seminary Hill Orchard & Cidery.
Where to eat and drink
Just under a mile from the Boarding House, Seminary Hill sits atop a seven-acre orchard, the skyward-pointing steeple of a former Catholic school visible through the dense tree cover beyond. In the tasting room, sit near the windows for views of the Delaware River and acres of old-growth forest clustered along the New York–Pennsylvania border.
The world’s first Passive House–certified cidery, Seminary Hill grows 61 varieties of apples and pears using holistic management practices. The tasting room menu features local ingredients in dishes like black cherry tamarind ribs, seared broccoli, and grilled focaccia smothered with za’atar. Pair with one of five ciders, from crisp, sparkling Northern Spy to citrusy, moderately acidic Delaware Dry.
Did a state already flush with craft beverage producers really need another? Yes, if we’re talking about Catskill Provisions Distillery. Located in a repurposed firehouse, Catskill Provisions makes small-batch bourbon, whiskey, vodka, and gin. Do a tasting of six spirits, or kick back with a creative cocktail (top picks: the maple margarita and hibiscus gin and tonic) and snacks like jackfruit tacos, bacon marmalade sliders, and local cheeses and charcuterie.
Across the street, at a renovated railroad house, locals line up for Callicoon Brewing Company’s beer on tap and classic pub fare: burgers, nachos, sandwiches, and meatloaf.
On Lower Main Street, Callicoon Wine and Tapas Bar specializes in European-inspired small plates. Prefer to sip back in your room? Its shop sells organic wines categorized not by varietals but by attributes like lush, crisp, fruity, and bold.
For the best breakfast in town, go to Callicoon Caffè. This local-favorite diner, in an old gas station, serves delicious budget-friendly standards like waffles, omelets, and breakfast sandwiches.
Things to do in Callicoon
The outdoors is king in Callicoon, and the best way to experience it is by raft, kayak, or canoe along the Delaware River. Launch your own boat from one of several public access points, or contact Landers River Trips to secure everything you need for a day on the water.
Back on land, walk the 20-acre Stone Arch Bridge Historical Park, or sign up for a guided nature experience—forest bathing, plant walks, sustainable foraging, and more—with the Outside Institute.
Avid hikers will want to head an hour north into Balsam Lake Mountain Wild Forest. The park surrounds 22 miles of scenic trails, from easy to a strenuous 6.7-mile path with a 1,500-foot elevation gain.
The hamlet is strong on boutique shopping. Start at the Antique Center of Callicoon, three stories packed with furniture, lighting, Depression glass, and more. Then stop in airy Litt Home & Book for vintage and new furnishings, gifts, and books, or PAO! for handmade statement jewelry and vintage clothing. Spruce Home Goods is an unusual fusion of local and international foods and home goods. Don’t miss the rustic breads and locally made ceramics. The arts are well represented, especially at nearby Museum at Bethel Woods, adjacent to the historic site of the legendary 1969 Woodstock festival. Back in the hamlet, Rafter’s Tavern is a quirky pub, art gallery, and live music venue in one. Or settle in for a first-run film at the Callicoon Theater, a renovated 1948 Quonset hut upgraded with modern sound and projection. You can even rent the theater for private screenings.
For a fringe-ier experience, head to Damascus, less than two miles over the Pennsylvania border, to Willow Wisp Organic Farm. In its greenhouse theater, the “perfarmers” of Farm Arts Collective stage plays, workshops, and other performances that highlight connection to place and the intersection of art and ecology.
How to get there
Callicoon is two hours northwest of New York City and two and a half hours southwest of Albany. The closest MTA train stop, in Port Jervis, is nearly an hour’s ride from town.
It’s more efficient, and far prettier, to drive into Callicoon, over winding, forest-shrouded backroads and past centuries-old farms and bite-size downtowns lined in historic architecture.