Unearth The Voyage
Nestled just a few hours north of New York City, the Catskills Mountains hide some of the most charming small towns in the Northeast. Whether you’re chasing brilliant autumn leaves, carving fresh powder on ski slopes, or floating down crystal-clear rivers, these villages offer year-round adventures wrapped in historic charm. Each town has its own personality, from artsy enclaves and fly-fishing meccas to colorful Victorian streets and cozy ski bases—making the region perfect for weekend getaways or longer escapes into nature.
1. Woodstock (Ulster County) — The Creative Capital
Long before anyone associated its name with a famous music festival, Woodstock earned its reputation as an authentic artists’ haven. The Byrdcliffe Arts Colony, established way back in 1902, still thrives today with rotating exhibitions, artist residencies, and beautifully preserved historic structures open to visitors.
Fun fact: that legendary 1969 concert actually happened sixty miles away in Bethel, but Woodstock’s creative energy inspired the festival’s name for good reason. Stroll Tinker Street to explore independent galleries showcasing everything from pottery to paintings, then catch a show at Kleinert-James or Byrdcliffe’s exhibition spaces. The town pulses with live music, quirky shops, and a bohemian spirit that feels timeless and welcoming all at once.
2. Phoenicia (Ulster County) — Tubing and Diner Culture
Forget lazy river floats—Phoenicia’s Esopus Creek delivers Class II white-water thrills that’ll get your heart racing. Local outfitters like Town Tinker rent tubes and shuttle you upstream for half-day adventures through rushing rapids and cool mountain water.
After you’ve dried off, head straight to the beloved Phoenicia Diner, where comfort food meets modern flair in a beautifully restored railcar setting. The tiny hamlet’s Main Street charm includes soft-serve ice cream stands perfect for hot summer afternoons. This spot thrives on its laid-back vibe, where tubing culture and good eats create the ultimate warm-weather escape without any pretense or fuss.
3. Tannersville (Greene County) — “Painted Village in the Sky”
Victorian storefronts burst with color along Tannersville’s Main Street, thanks to a town-wide initiative that transformed this mountain village into a kaleidoscope of painted facades. The nickname “Painted Village in the Sky” fits perfectly—national publications have celebrated its cheerful aesthetic and Instagram-worthy charm.
Positioned high in the Greene County mountains, Tannersville serves as an ideal launching point for exploring Kaaterskill Falls and the scenic trails around North-South Lake. Wander Main Street to discover murals, cozy cafés, and boutiques tucked inside those brilliantly painted buildings. Fall brings spectacular leaf-peeping opportunities, when the surrounding forests compete with the town’s vibrant architecture for your camera’s attention.
4. Hunter (Greene County) — Big Mountain, Tiny Town
Hunter Mountain stands tall with serious skiing credentials: 1,600 vertical feet, more than sixty trails, and aggressive snowmaking that extends the season when Mother Nature doesn’t cooperate. The resort dominates this tiny Greene County village, but the pairing of major mountain amenities with small-town atmosphere creates something special.
Winter transforms Hunter into a bustling ski hub, but don’t overlook the warmer months when scenic chairlift rides reveal breathtaking valley views and trailheads lead to hidden waterfalls. The village itself stays refreshingly low-key despite the resort’s popularity, offering aprés-ski spots and local eateries where you can swap trail stories with fellow adventurers after a long day on the slopes.
5. Windham (Greene County) — Four-Season Resort Town
Just down the road from Hunter, Windham offers its own compact ski-town charm with a walkable village core that feels welcoming year-round. Windham Mountain recently repositioned itself as an upscale four-season destination, stepping away from Ikon Pass access while raising season-pass prices to cultivate a more exclusive atmosphere.
The mountain still delivers excellent lift-served terrain for skiers and riders, plus expanding summer mountain biking trails that attract two-wheeled adventurers. Classic Main Street shops and restaurants give the village genuine character beyond the resort amenities. Whether you’re planning winter laps, summer trail rides, or autumn hikes through fiery foliage, Windham balances resort convenience with authentic mountain-town hospitality.
6. Livingston Manor (Sullivan County) — Catskills Fly-Fishing Hub
Upstream from Roscoe on the legendary Willowemoc Creek, Livingston Manor—affectionately called “The Manor”—blends world-class trout fishing with surprising modern touches. Craft breweries, design-forward inns, and farm-to-table restaurants have transformed this Sullivan County hamlet into more than just an angling destination.
The Catskill Fly Fishing Center & Museum preserves the region’s rich fishing heritage with exhibits and programs, while the Willowemoc itself provides gorgeous water for working your cast. Between fishing sessions, grab a pint at Catskill Brewery or explore the revitalized Main Street shops. The Manor proves you can honor tradition while embracing contemporary mountain-town culture, creating a perfect balance for anglers and non-anglers alike.
7. Roscoe (Sullivan County) — “Trout Town, USA”
Where the Beaver Kill meets the Willowemoc, Roscoe has earned every bit of its “Trout Town, USA” nickname. This confluence creates legendary fly-fishing water that draws anglers from around the globe, making early-morning pilgrimages to cast over rising trout in pristine Catskills streams.
The hamlet embraces its angling identity without pretension—local outfitters provide gear and guidance, public stream access points dot the area, and Stewart Avenue’s laid-back cafés fuel pre-dawn expeditions. Even if you’ve never held a fly rod, Roscoe’s quiet riverside charm and mountain scenery make it worth exploring. Coffee shops and casual eateries welcome visitors year-round, creating a peaceful base for Catskills adventures beyond the water’s edge.
8. Narrowsburg (Sullivan County) — River Town With an Artsy Core
Perched on a dramatic curve of the Delaware River, Narrowsburg surprises visitors with its indie arts scene anchored by the historic Tusten Theatre. This Sullivan County gem balances riverside recreation with cultural offerings, creating an unexpectedly sophisticated small-town experience.
Browse eclectic shops selling handmade goods and vintage finds, then catch a performance at the beautifully restored theater. Winter brings a special treat: bald eagles migrate to the Upper Delaware Scenic & Recreational River, and viewing sites right in town offer front-row seats to these majestic birds. Warm-weather months invite paddling, swimming, and riverside picnics. Narrowsburg’s combination of natural beauty and creative energy makes it stand out among Delaware River communities.
9. Callicoon (Sullivan County) — Vintage Main Street on the Delaware
Country Living magazine once spotlighted Callicoon’s compact Main Street, and one stroll explains why. This Sullivan County village preserves vintage charm through its boutiques, historic single-screen theater, and seasonal festivals that bring the community together along the Delaware River.
The rebuilt depot now serves as a visitor center, providing information for exploring the Upper Delaware’s paddling routes and winter eagle-watching opportunities. Farmers’ markets during warmer months showcase local produce and crafts, adding to the town’s authentic appeal. Callicoon feels refreshingly unhurried—a place where you can window-shop, catch an indie film, and watch the river roll by without anyone rushing you along. It’s small-town America at its most genuine and welcoming.
10. Margaretville (Delaware County) — Round Barn Market & Mountain Vibes
Saturday mornings from mid-May through November (plus holiday dates) mean one thing around Margaretville: the beloved Pakatakan Farmers’ Market at the historic Round Barn in nearby Halcottsville. This iconic structure hosts vendors selling everything from organic vegetables to artisan breads, creating a community gathering spot that locals and visitors cherish equally.
The village itself sits along the East Branch Delaware River, offering low-key access to hiking, skiing, and scenic mountain drives without crowds or commercialization. Main Street’s mom-and-pop shops and casual eateries maintain an authentic Catskills feel. Margaretville serves as an understated base camp where outdoor adventures and agricultural heritage blend naturally, perfect for travelers seeking genuine mountain-town experiences.
