New York’s Sullivan Catskills:

Charming Small Towns Full of Big Experiences

Just 90 minutes from New York City, the Sullivan Catskills is a legendary destination known for its warm, friendly hospitality. Over nearly 1,000 square miles, this picturesque county is a collection of charming small towns full of adventure, extraordinary cuisine, arts and culture, and outstanding accommodations. 

The Main Streets are framed by historic former hotels, mercantiles, apothecaries, taverns, firehouses, boarding houses turned art and antique galleries, acclaimed restaurants, intriguing small shops, studios, and bookstores. Relive calmer days when the world moved slower with the simpler rhythms of rural hamlet life. Relax, browse, and visit the farmers’ markets and country fairs.  Hike through seasonal splendor, paddle a kayak, fish world-class streams, and read a book by the fire in a bakery. World Atlas once rated the river town of Narrowsburg as one of the top 12 small towns in the U.S. Don’t miss Barryville, Callicoon, Jeffersonville, Livingston Manor, Mountaindale, Roscoe, or Wurtsboro.

These small towns are “inn” places. Why go west when you can stay east at an authentic ranch experience that Beth Dutton would love? The Robb Report named White Lake’s Driftwood Ranch— a working horse and cattle ranch with horseback riding, hiking, fishing, and four luxury suites— number 19 of the 50 Most Hotly Anticipated Luxury Hotel Openings for 2025. And the restaurant at Livingston Manor’s The Debruce received a 2024 semifinalist nod from the James Beard Foundation.

Big song and dance. The 1969 Woodstock Music and Arts Fair (held in Bethel) wasn’t small. But it was a town with stores, food, and entertainment. The site has been transformed into Bethel Woods Center for the Arts. You can visit the site, hear the echoes, and then stay for the big-name concerts at the Pavilion (Dave Matthews Band, Luke Bryan, and Avril Lavigne are among the early May-June shows in 2025). Enjoy professional theatre in a barn at Forestburgh Playhouse in the summer months. See an opera lakeside at the Delaware Valley Opera in Lake Huntington. Or hear a classical music festival on top of a mountain at the Shandelee Music Festival. And there are galleries galore, full of modern makers and artists. Want to try your hand? There are workshops and studios. You can throw a plate, try a tune, or tie a fly. If all the world is a stage, The Sullivan Catskills is in the spotlight. 

Dining with extraordinary service, style, and personality. Who are we to argue with the Michelin Guide to Hotels and Dining? They savored spectacular food in a cidery overlooking the Delaware River Valley and a restored small hotel with a wedding barn. You can, too. From Linguinette to D’Oro Supreme, it’s all Catskill-icious freshness, variety, and flavor. There’s also a Diner Trail, the Good Taste Craft Beverage Trail, and farm markets. 

Gateways to big adventures There’s a legendary Monster in these mountains. It’s green, and it lives next to a casino. People like you come from all over the world to challenge it with clubs. It’s the Monster Golf Course at Resorts World Casino in Monticello. Elsewhere, you can hook a monster trout in the legendary Beaverkill River or Willowemoc Creek. Raft the Delaware River and hike in the forests— dozens of trails suit all fitness levels. Track down the 70+ colorful doves on the Sullivan Catskills Dove Trail, a tribute to the 50th anniversary of the Woodstock festival. 

New York’s Sullivan Catskills is the best of all worlds for relaxation and recreation—small and friendly, big on fun and entertainment choices. All are easy to reach and just a short drive apart. You’ll leave refreshed in no small way for a weekend escape or extended stay. And that’s a big deal.