In the age of micro-adventures, quick weekend getaways and unforgettable Instagram moments, voyagers are finding new inspiration in relatively unknown places. To discover your own unique small town adventure, look no further than the Catskill Mountains. Spanning four of New York’s most beautiful counties, the region’s wild lands are dotted with small, Americana towns perfect for your next vacation.
Guide to Small Towns in the Catskills
1. Windham
Established over 200 years ago in 1798, Windham is one of the oldest towns in the region. Often called the “gem of the Catskills,” Windham’s quaint and charming downtown will take your breath away. Take a walk down the historic main street to shop boutique stores, or choose a more active day on mountain bike and hiking trails or the golf course. When hunger strikes, find mouth-watering refreshments at locally-owned Catskills restaurants with world-class ratings. Despite being small, the town is well-versed in hospitality, offering a wide selection of bed and breakfasts, inns and resorts many with direct views of Windham Mountain.2. Catskill
Along the banks of the Hudson River, Catskill is a Greene County town steeped in history. Home to Thomas Cole, the founder of the Hudson River School of Art and widely considered the father of American art, Catskill is a cultural hub year round. From small downtown galleries to the Thomas Cole National Historic Site, you will find stunning works by up-and-coming artists as well as timeless legends. Experience for yourself the view that has inspired artists for years atop the Hudson River Skywalk. A mile-long pedestrian bridge spanning the Hudson, the Skywalk provides stunning views of the river and surrounding valley and connects Cole’s homestead and Olana, home of famed Hudson River School painter Frederic Church.3. New Paltz
If you’re in the mood for somewhere hip and happening, make your way to New Paltz, a small Catskills college town that abuts the rugged Shawangunk Ridge. From scenic hikes with spectacular views to renowned rock climbing at the ‘Gunks and breathtaking lakes, New Paltz is a gateway to natural wonders. It’s also a place where art and culture flourish alongside bucolic farm fields and bountiful orchards. Spend a day exploring in Mohonk Preserve or Minnewaska State Park, then drop down into town for a locally-sourced meal and a fresh brew from a local brewery or cider house. If nature’s not your game, no worries. New Paltz’s Main Street has plenty of shops, coffee houses, restaurants and performance venues to discover. Of the towns in this list, New Palz is probably the quickets to reach from NYC.4. Woodstock
While the small town of Woodstock has become synonymous with the world-famous 1969 festival, it wasn’t the original site of the peace, love, and music event that made history. It is, however, the perfect place for a relaxing weekend. Home to Byrdcliffe Art Colony, the nation’s oldest arts and crafts colony, the town has welcomed artists and musicians with open arms for over a century. Live music events are a staple in Woodstock. Surrounding the village green at the center of town you will find unique shops selling handmade crafts from local and visiting artisans. Whether you’re looking for creative inspiration, or just a one-of-a-kind stay, Woodstock is a small town you don’t want to miss.5. Bethel
The Woodstock Music Festival’s true home was Yasgur’s farm in Bethel, NY. Located in Sullivan County, less than 50 miles south of the festival’s namesake town, Bethel has been forever shaped by the events that took place in 1969. Learn all about the Woodstock festival and its lasting legacy at Bethel Woods Center for the Arts. You can walk the hallowed grounds where musical magic happened, visit the museum and catch a live performance at one of their outdoor or indoor stages. 6. Roscoe Known as Trout Town USA. Roscoe is famous for its ultimate angling opportunities. But there are plenty of other happenings that will provide a well-rounded upstate New York experience to visitors of this southwestern Catskills town. Dine at the Rockland House for an unforgettable meal prepared by acclaimed chefs. Enjoy a pint at the Roscoe Beer Company’s Store Front, a former firehouse turned brewery. Or sample award-winning Bootlegger New York Craft Vodka at Do Good Spirits, open every day, all year on Union Street. Sleep along the shores of Beaverkill River at a campground or stay at one of several nearby inns, motels or other lodgings. From Alpaca farms to fishing trips, and galleries, there is something for everyone to do and see in Roscoe.7. Roxbury
What was once a small farm town is now a vibrant community and must-see destination in Delaware County. Much of Roxbury’s beauty lies in its history, boasting landmarks like Roxbury Barn, a 167-year-old mountain estate, and Woodchuck Lodge, built in the 1860s, owned by naturalist-essayist John Burroughs, and named a National Historic Landmark in 1962. Roxbury is home to Plattekill Mountain, a family-friendly, laid back ski mountain that is one of the few remaining privately-owned operations in the country. Creativity is part of the town’s pulse with the Roxbury Arts Group offering performances, exhibitions, workshops and classes for adults and children. Creative flair is alive and well at the Roxbury Contemporary Catskill Lodging, a boutique motel experience offering wildly decorated theme rooms. If nothing else, make the trip to Roxbury just to stay in the motel’s Archaeologist’s Digs Cottage.8. Margaretville
For a sophisticated small town stay in the Catskills, visit Margaretville. There, you will eat, drink, and sleep like a king or queen. Dine at Trattoria Locale, a family-owned Italian restaurant with daily and seasonal specials inspired by the local farmers’ market. Or, stop into the Binnekill Tavern, a Margaretville landmark and quintessential mountain tavern focused on Swiss-German cuisine. Choose from a wide variety of lodgings, including the rustic-elegant Hanah Mountain Resort and Country Club or log-framed Whispering Pines Lodge,. For a truly soul-cleansing retreat, stay at the Blue Deer Center, which offers workshops and holistic retreats based upon ancestral traditions that help to connect participants to the natural world.
