Top Catskills Small Towns for Hiking, Charming Hotels, and Breweries

Fact checked by

Jillian Dara

Look, things change. We didn’t need a pandemic to tell us that the Catskills have evolved with the times. Harried city dwellers rushing to the Borscht Belt have accelerated the region’s renaissance, which was already on the precipice of a revival.

Nonetheless, that old truism that the more things change, the more they stay the same never rings louder than in the storied Cats. Take locals of Fallsburg, for instance, who still aren’t over the recent shuttering of Frankie & Johnny’s Nardi’s Italian Restaurant after four decades of heaping comfort food platters. While there’s nothing we can do to quell the blow, we can tell you that there’s just something about the air up here, the slant of the morning light, even the echoes of tennis balls reverberating in the cradle of cordilleras, that make all these transformations work. All of that has stayed the same in these hallowed hills.

Yes, there’s a dizzying slate of incredible new restaurants, hotels, and experiences in these parts (and we’ll happily point you in the right direction). But at the end of the day, what makes the towns below worth journeying to are the very gulps of mountainous ether and endless green landscapes that have been here for time immemorial. Here, the very best small towns in the Catskills to visit.

Monticello

With all due respect to Thomas Jefferson and his Charlottesville Estate, New York’s Monticello sets the bar really high — and we’re not just talking about the towering, age-old peaks of the Catskills’ verdant ranges. Here, visitors can chase adrenaline highs at the Monticello Motor Club, big wins at Resorts World Catskills (a great place to stay and kiddos will love the adjacent Kartrite Resort & Indoor Waterpark), and chakra euphoria at the Ayurvedic luxury health resort Yo1.

For a private getaway, set up shop at Red Cottage Inc.’s Crosslands two-bedroom home, one of our favorite abodes in their curated portfolio of chi-chi vacation rentals, this one with a fireplace, swimming pond with a dock, hot tub, fire pits, gas barbecue grill, and more.

Roscoe

This Sullivan County hub gives off serious ’50s summer camp energy. While there’s a dizzying array of camping options in “Trout Town USA,” our vote is the unique Roscoe Campsite, where you can channel your inner pioneer person and sleep in a covered Conestoga wagon. Or, for another one-of-a-kind digs, venture to Buck Brook Alpacas, which operates an Airbnb listing on the farm where you can walk, feed, and pet the alpacas to your heart’s content. Either way, reward yourself for roughing it in nature with a tipple at Roscoe Beer Co. or Navy veteran-founded Do Good Spirits, or a crock of French onion soup and a panini at Roscoe Diner.

Round Top

For something off the beaten path — for now — try Round Top (and the adjacent hamlet of Purling) in Greene County. Expect German-American spirit and grub galore with properties such as Riedlbauer’s Resort, The Bavarian Manor Country Inn and Restaurant, and Crystal Brook Mountain Brauhaus. If you prefer to relegate your Bavarian fix to mealtimes only, try lodging at Winter Clove Inn or the Glen Falls House.

The Great Northern Catskills region abounds with natural splendor. Biking enthusiasts will rejoice in “Roundtopia,” a network of first-rate mountain biking trails. Hikers can hit up East Kill Falls for a 7.2-mile trek brimming with breathtaking views, or form sylvan memories at Whip-O-Will Campsites. Adirondack chair sitters will be pleased to melt the day away with a book or a sketchpad sans sweat by plopping down at Glen Falls, a swimming hole with a waterfall view on-site at the eponymous resort. For some indoorsy fun, skate the night away at Cairo Purling Roller Rink, a 1950s-era gem that will make you want to return to the city, well, never.

Bethel

Once upon a time, there was this not-so-little-thing called Woodstock. Bethel is home to the National Historic Site of the 1969 Woodstock Festival. The town is also known for Bethel Woods Center for the Arts (which has drawn acts as diverse as the Dave Matthews Band, the New York Philharmonic, Crosby, Stills, Nash & Young, and Santana).

When hunger strikes, mosey on over to the Dancing Cat Saloon, where Catskill Distilling Company is also located. In the winter, the enchanting Peace, Love & Lights show is a good itinerary swap for patio hangs and live music sessions at the ol’ Dancin’ Cat. Traveling with a group? Come nightfall, check out Red Cottage’s The Homestead on picturesque Kauneonga Lake (also known as White Lake), a 14-bedroom lakefront compound with a fireplace, kayak and water toys, fire pit, and a modern chef’s kitchen. The rental company’s Journey’s End and Deer Meadows are two other stellar and smaller options in the town of Bethel.

Fallsburg

Nothing plucks at your heartstrings like a good Main Street? Then head to Fallsburg’s hamlet of Hurleyville, an under-the-radar jewel of Sullivan County. There, you can fuel up at the award-winning Pickled Owl restaurant, check out Fiber on Main yarn store, and experience Hurleyville Arts Centre (new to the Centre is Tango Cafe, a restaurant from celebrated chef Tom Valenti, best known for his days as executive chef at Le Cirque and his former restaurant Oxbow Tavern in Manhattan). Other worthwhile pit stops include the recently opened La Salumina charcuterie shop and Fortress Bikes for bike and snowshoe rentals. Speaking of which, when you’re ready to bike, hike, or snowshoe the trails, you’ve found your perfect match in the O&W Rail Trail which passes through storybook villages like Woodridge and Mountaindale (after a walk along soul-restoring and aptly named Pleasure Lake, drive on Davos Road to Witchey Handmade Herbal Apothecary for some gifts for the folks back at home).

Margaretville

Another idyllic stroll on Main Street awaits, this time in Delaware County. Pop into apothecary Species by the Thousands for a candle, aromatherapy oils, or jewelry before continuing your apothecary tour onto Honeybee Herbs where you’ll want to stock up on jars of their herbal tea blends, raw honey, and a motley assortment of tinctures. Once you’ve worked up an appetite, try quintessential mountain town haunt Binnekill Tavern, coffee and pastry haunt Café Marguerite (the smoked salmon on an everything croissant is always a good idea), family-owned Trattoria Locale for delectable Italian fare, and recently opened, health-focused eatery Lucky Sparrow Kitchen. Pro tip: Place a family-style catering order to bring on a day of hiking at nearby spots like Dry Brook Ridge Trail, Kelly Hollow Loop, or Huckleberry Loop.

When it’s time to seek salvation for your sapped calf muscles, stay at Belle Ayre House, an inviting and meticulously restored three-bedroom farmhouse; Groovy Chalet for easy access to hiking trails and skiing; the Homestead Farm Resort (est. 1819); or Hanah Mountain Resort & Country Club if you seek a more traditional hotel experience. If you can, reserve a workshop or retreat at the Blue Deer Center, a nonprofit that creates programs around ancestral wisdom and healing principles before your time in Margaretville is complete.

Roxbury

First stop: The Watershed, “Roxbury’s front porch,” which has visitors covered from morning coffee to last-call cocktails. Properly caffeinated, head to Plattekill Mountain for some skiing, snowboarding, mountain biking, or a scenic chairlift ride in this beautiful pocket of the Western Catskills. Located in Delaware County, Roxbury also boasts historic Kirkside Park, a one-time estate turned into an 11-acre public park and an ideal spot for a seasonal picnic. When it’s time for sustenance, head to The Fierce Grizzly, which doles out elevated continental cuisine in a former tin shop.

For your home away from home, Bellfire in the Catskills on Bellfire Farm offers an off-grid tented experience or a tiny home with a six-foot skylight and 11-foot windows in the living area. There are also rooms to rent in the farmhouse. More stellar lodging options include The Roxbury Motel and The Roxbury at Stratton Falls, both offering themed rooms with whimsical design.

Catskill

This remote town in Greene County is home to some of the hottest craft beverage spots in the state, such as Subversive Malting Brewing and Left Bank Ciders. For shopping enthusiasts, a winning Main Street entices with independently owned shops and restaurants like New York Restaurant, featuring Polish and American hits with vegan and gluten-free dishes thrown into the mix. Other Main Street standouts include Willa’s (two words: cinnamon buns) and Citiot, a hybrid coffee shop and art/gift store.

When you’re ready to call it a night, meander on over to the recently opened Piaule Catskill, which has 24 guest cabins on forested grounds, an on-site restaurant and bar, spa and wellness center, and countless hiking trails. Before you skip town, visit Thomas Cole National Historic Site, where the famed artist who founded the Hudson River School of American painting lived and worked.

Windham

Pack your gym clothes and/or ski gear: between Windham Mountain, Windham Mountain Bike Park, and the Windham Path, there’s no shortage of opportunities for active fun from fly-fishing to skiing in this tiny town in Greene County. Alternately, swap adrenaline for resveratrol at The Vineyard at Windham, a four-acre oenophile’s paradise with wonderful views of its namesake mountain.

We’re swooning for the Scandinavian-inspired Lushna Suites at the Eastwind Hotel & Bar; they’re glamping cabins that come outfitted with a lofted queen bed with an A-frame window, full-size sofa bed, writer’s nook, bathroom with a windowed shower, deck with patio furniture, fire pit, outdoor shower, and hammock. Or, set your sights on the Union & Post boutique hotel and restaurant, a design-forward oasis from the hustle and bustle of urban living.

Livingston Manor

There’s good reason we named Livingston Manor one of the best small towns in New York. Talk about an interesting town doing interesting things — it’s a bit like a real-life Schitt’s Creek — so much so that it’s converting tourists into new residents. One of the key players in re-imagining this mountain town is Sims Foster of Foster Supply Hospitality. FSH is behind The Arnold House (share their smoked trout dip with someone you love after a long drive up from the city) and The DeBruce, a bucolic boutique hotel and veritable epicurean oasis. Sims has also redeveloped old motels into handsomely preserved properties. The Catskill Project is also worth keeping your eyes on, a carbon-neutral and completely regenerative housing community perched on 90 acres in this once sleepy river valley town.

Development bonanza aside, tourists should be sure to visit The Catskill Fly Fishing Center & Museum, an anglers’ heaven; Upward Brewing, where two friends and many a Craigslist find resulted in one of the most stunning breweries in the area (don’t miss the black pilsner); and Sullivan County-based The Outside Institute, a naturalist program with private walks, foraging excursions, botanical mixology classes, and more.