Think of the Catskills not as one sprawling blanket of 5,892 square miles, but as a constellation of idyllic towns, each with its own distinctive factors—from farm-to-table taverns to tucked-away artisanal breweries, cozy inns, and well-curated markets. What really makes this corner of New York irresistible is the exodus of Brooklyn and Manhattan creatives who’ve transplanted their craft here: acclaimed food, boutique beer, wellness retreats—all framed by forested mountains and wide-open skies. Whether chasing a luxe resort along the Hudson or a quaint place in a tucked-away hamlet, you’ll almost always find yourself simultaneously recharged, well-fed, and quietly in love with the Catskills’ unassuming charm.
The landscape—just a two-hour drive north of Manhattan—has slowly shed its insider status to become a bucket-list stop for adventurers from every corner of the country, but there's still much to discover. Here’s your roadmap to veering off the beaten path in the Northern Catskills.
One of the Catskills’ draws—especially for the well-traveled—is not just miles of forest; it’s discovering a place that feels handpicked for you. Here, each stay can be wildly varied—from minimalist Scandinavian-style sanctuaries like Inness to sought-after destination resorts like Wildflower Farms, alongside rediscovered country inns that strike a balance between intimacy and white-glove service.
The Henson in Hendersonville is one of those places, housed in a 160-year-old building and reimagined by the team behind Wildair and Contra's wildly popular NYC restaurants. Inside, original wood-beam ceilings and maple-plank floors sit alongside vintage furnishings and contemporary art, creating interiors that feel both lived-in and comfortably modern. In winter, the cozy living room with a fireplace, library, and bar fosters a relaxed, slow-paced atmosphere; in summer, the hidden rooftop and walled garden feel like a private sanctuary.
The hotel’s sixteen rooms are just as unique: some have pitched ceilings and large windows framing mountain views, while others feature restored fireplaces or deep claw-foot tubs. Instead of a uniform corridor of identically decorated spaces, each suite resembles a friend’s lovingly renovated guest cottage. Mornings begin in a bright dining room with pastries, freshly brewed coffee, and juices before you grab your bespoke Catskills field guide—a custom-curated guide to tucked-away hikes, local breweries, and farmers markets—and head out for the day.
Trade your morning commute for a choice of a few very different wake-up calls: the quick, pulse-raising climb to Kaaterskill Falls, featuring its main attraction—a majestic 260-foot curtain of water, a hike up to Hunter Mountain's Fire Tower for more pictruesque views, or the Windham Path’s level meadow loop, a less strenuous stroll that frames the Catskill peaks.
With legs fully loosened, coast down to GardenHeir’s curated shop (also known for outfitting the store at Wildflower Farms in Gardiner), where stoneware planters, hand-loomed shackets, gardening clogs, tools, and independently owned clean beauty brands create a “souvenir” from the area that feels entirely sophisticated. Lunch is best enjoyed with a local beer: West Kill Brewing pours a bright, hay-flecked farmhouse ale on a deck that places you at treetop level while local bluegrass bands play below. If the afternoon calls for quiet, pick up a summer read or a local hiking guide at Briars and Brambles and retreat to the Hensons' garden or rooftop deck.
Don’t mistake Hensonville’s relaxed atmosphere for sleepy. The upper Catskills are in the midst of a quiet food renaissance, thanks to a steady migration of city-trained talent and hyper-local purveyors who treat mountain produce with the utmost respect. Your breakfast can start right next door at Para Casa, a postage-stamp pantry where strong cortados share counter space with homemade pastries and shelves of small-batch pantry goods. Then, a 20-minute drive lands you at the iconic Phoenicia Diner, where duck-fat hash browns and buckwheat pancakes prove the blue plate can still surprise and delight. Afternoons are best spent at West Kill Brewing: claim a perch on the treetop deck, nurse a saison, and graze through whatever inventive food truck has rolled in. For dinner, head home to Matilda at The Henson, where Jeremiah Stone and Fabián von Hauske Valtierra channel the region’s bounty into a dinner that rivals any in New York City: comté with country ham and blistered sourdough, confit tuna belly, wood-grilled oysters, and a Hudson Valley trout or grass-fed steak paired with the perfect wines and craft cocktails. Leave room for dessert—Matilda’s pastry team treats the sweet course with just as much care. You’ll soon understand why locals keep their favorite addresses close—and why the rest of us just keep finding excuses to come back.
