The Catskill Mountains offer more than just stunning landscapes and outdoor adventures. Nestled throughout this region of upstate New York are delightful small towns with unique character and rich history. These communities blend artistic cultures, preserved architecture, and welcoming atmospheres. Just a few hours from New York City, these towns provide perfect escapes from urban life without sacrificing comfort or culture. Each destination offers its own specialties while sharing the relaxed mountain lifestyle that makes the Catskills special.
Woodstock
This iconic town earned fame from the 1969 music festival (which actually happened in Bethel), but maintains its own artistic legacy. Gallery-lined streets feature local artwork, while musicians perform in cafes and on street corners. The Woodstock Artists Association and Museum showcases regional talent spanning decades. Hiking trails like Overlook Mountain provide spectacular views after moderate climbs. The town center buzzes with independent shops, farm-to-table restaurants, and a weekly drum circle that continues the free-spirited tradition.
Phoenicia
This tiny hamlet along the Esopus Creek serves as a gateway to outdoor adventure. Tubing down the creek provides summer fun, while nearby hiking trails offer experiences for all skill levels. The Phoenicia Diner, housed in a retro building, draws visitors for elevated comfort food using local ingredients. The town’s main street features antique shops, a old-time general store, and cozy bookshops. Train enthusiasts enjoy the Catskill Mountain Railroad, which runs scenic trips through the surrounding countryside.
Tannersville
Known as “The Painted Village in the Sky,” Tannersville features vibrantly colored Victorian buildings along its main street. This once-sleepy town has transformed through a revitalization project that brought artists and entrepreneurs. Outdoor enthusiasts appreciate its proximity to Hunter Mountain’s skiing and hiking trails. The Deer Mountain Inn offers fine dining in a historic lodge setting. Local shops sell everything from antiques to locally produced maple syrup. The Mountain Top Arboretum provides beautiful gardens with native plant species and walking paths through various ecosystems.
Narrowsburg
Perched dramatically above the Delaware River, this tiny town delivers big on charm. Eagle watching draws nature enthusiasts during winter months when the birds fish in the unfrozen river. The Narrowsburg Union houses galleries, workspaces, and a small theater in a repurposed school building. Main Street shops offer curated vintage collections, handmade ceramics, and unique home goods. Foodies appreciate the surprising culinary scene featuring farm-to-table restaurants and an annual honey festival. The river provides opportunities for canoeing, kayaking, and fishing.
Saugerties
This historic town where the Esopus Creek meets the Hudson River blends working waterfront with artistic community. The Saugerties Lighthouse, accessible by a half-mile trail, offers overnight stays in a restored 1869 landmark. Opus 40, a sprawling bluestone sculpture park, showcases one man’s 37-year artistic vision. The downtown area features well-preserved 19th-century architecture housing independent shops and restaurants. Horse lovers visit for HITS (Horse Shows in the Sun), which brings equestrian competitions throughout summer months.
Delhi
This college town maintains its agricultural roots while embracing new energy from SUNY Delhi students. The well-preserved downtown features Victorian architecture alongside modern farm-to-table restaurants. The West Branch Delaware River runs through town, offering fishing spots and scenic walking paths. Local farmers markets showcase regional produce, artisanal cheeses, and handcrafted goods. Hollow works brewery serves craft beers in a renovated historic building. The Delaware County Fair, held each August, continues agricultural traditions with livestock competitions, tractor pulls, and homemade preserves contests.
Andes
This tiny hamlet has transformed from farming community to arts destination while maintaining its rural charm. Antique shops and galleries occupy former dairy farm buildings along Main Street. The Andes Hotel, operating since 1850, serves comfort food classics with modern twists. Outdoor enthusiasts enjoy proximity to hiking trails and the pristine Pepacton Reservoir for kayaking. Community events like farmers markets and summer street festivals bring locals and visitors together. The surrounding mountains provide spectacular fall foliage views and winter landscapes.
Margaretville
Located along the East Branch of the Delaware River, this friendly town serves as a regional hub for several smaller communities. The historic Binnekill Square features shops selling local crafts, books, and specialty foods. The Catskill Recreation Center offers a modern swimming pool and fitness facilities unexpected in such a small town. Outdoor activities include fishing, hiking, and skiing at nearby Belleayre Mountain. The Open Eye Theater presents professional productions in an intimate setting. Local restaurants emphasize farm-to-table dining with ingredients from surrounding valleys.
Roxbury
This storybook town features remarkably preserved Victorian architecture thanks to the wealth of the former Delaware & Ulster Railroad. The Roxbury Arts Group occupies a converted Gothic church, hosting performances and exhibitions throughout the year. The Roxbury Motel offers whimsical themed rooms inspired by different decades, drawing visitors seeking unique accommodations. Outdoor adventures include fishing in the clear streams and hiking nearby trails. The town’s pride comes through in well-maintained gardens and historic markers explaining local history. Community events include summer concerts and harvest festivals.
Hunter
While best known for Hunter Mountain ski resort, this village offers year-round charm beyond winter sports. The Mountain Creek Falls provides a dramatic backdrop visible from several points in town. Kaaterskill Falls, the state’s highest two-tier waterfall, lies just outside town limits. Summer brings mountain biking, zip-lining, and hiking opportunities on the same slopes used for skiing. The Catskill Mountain Foundation hosts performances ranging from classical music to modern dance. Small restaurants serve hearty meals perfect after a day of outdoor adventures.
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