7 Charming Small Towns in the Catskills—With Retro Diners, Wood-fired Hot Tubs, and New York’s Most Beautiful Waterfall

Livingston Manor

Livingston Manor has that “‘cool but not trying too hard’ vibe—it’s artsy, outdoorsy, and delicious all at once,” says Lisa Karvellas, co-founder of Cedar Lakes Estate in nearby Port Jervis. She suggests grabbing local goods at Main Street Farm, a pint at Catskill Brewery, and wood-fired pizza under the string lights at The Kaatskeller—or making the drive to Brushland Eating House in Bovina, which she calls “cozy, beautiful, and unforgettable.”

Carly Fisher, author of “Easy Weekend Getaways in the Hudson Valley & Catskills,” adds that the hamlet delivers “the best of all worlds”: cute boutiques like Nest and Homestedt, a wine bar (Sunshine Colony), breweries (Catskill, Upward), and even a nearby James Beard–nominated restaurant (The DeBruce), all while being minutes from the Catskill and Delaware Rivers and Willowemoc Wild Forest. That means you can spend one day hiking Frick Pond Loop or fly-fishing with the pros at Dette Flies and the next strolling Main Street with a coffee and shopping for artisanal goods.

Cooperstown

According to Dawn Gertner, head concierge at The Otesaga Resort Hotel, Cooperstown more than lives up to its nickname, “America’s Most Perfect Village.” “Though the population is small, you’ll find it brimming with history and small-town charm,” she says. The National Baseball Hall of Fame and Museum anchors Main Street, which is dotted with mom-and-pop restaurants and shops like Doubleday Cafe, Stagecoach Coffee, Baseballism, and Tin Bin Alley, while the Fenimore Art Museum and Fenimore Farm & Country Village offer a deeper dive into the region’s culture. Gertner also points visitors to local favorites, like the bustling farmers market or brunch at 1909, the Otesaga’s lakeside restaurant, where sweeping water views make the experience as memorable as the food.

Windham

Nicknamed the “Gem of the Catskills,” Windham has been welcoming visitors since 1798, and today it strikes the right balance between small-town hospitality and mountain adventure. At its heart is the Windham Mountain Club, which boasts outdoor sports, eateries, a spa and fitness center, a boutique, and much more. While very much a playground for skiers in winter and hikers or mountain bikers the rest of the year, it offers a layer of luxury that turns heads across the Catskills. Just outside town, the Windham Path winds through meadows and woodlands, while a short drive away, the dramatic two-tiered Kaaterskill Falls—at 260 feet, the tallest cascading waterfall in New York—is a must-see.

For a more intimate, family-run experience, head to Bearpen Mountain Sports, where you’ll find cross-country skiing, fat-tire biking, and tubing once the snow piles high. Downtown centers on Route 23, better known as Main Street, where cafés, galleries, and mom-and-pop shops give Windham its hometown warmth. That said, my favorite part of staying here was checking into Eastwind: a boutique retreat with Scandinavian-inspired rooms, suites, and A-frame Lushnas (glamping-style cabins). Here, breakfast baskets are delivered directly to guests’ doorsteps, and the freestanding dry saunas offer a restorative retreat after a day outdoors.

Callicoon

Callicoon may be small, but it punches above its weight with a mix of heritage and fresh energy. On Sundays, I always make time for the farmers market—one of the best in the Catskills—before wandering Lower Main Street, where shops like The Farmhouse Project and Lee Hartwell Antiques sit alongside cozy spots like The Creek House Grill and Peppino’s. When I stayed at Callicoon Hills, the 23-acre property felt like the town in miniature form: a historic boarding house reimagined as a boutique retreat, with 65 guest rooms and hillside A-frame cabins. Evenings around the fire pits and in the tavern had a social, almost summer-camp vibe that made it easy to settle in.

Just up the road, Seminary Hill is a working orchard and cidery with a gorgeous timber-frame tasting room that boasts pristine views of the Delaware River and beyond. Callicoon’s beverage scene continues to impress, with other must-visits like Catskill Provisions Distillery, known for its honey-based spirits and inviting tasting room, and the Callicoon Brewing Company offering craft beers, ciders, and pub grub overlooking the Delaware River.

Phoenicia

Right on the Esopus Creek in the heart of the Catskills, Phoenicia is equal parts artsy and outdoorsy. Breakfast here is practically a rite of passage. You’ll find folks from across the region lining up at Phoenicia Diner on Route 28, a popular spot for its retro-cool vibes and farm-to-table comfort fare, such as fluffy omelets and egg skillets.

Alternatively, for a less-crowded pick, make a beeline for Bettina Café & Market. Right on Main Street, this centrally located haunt serves crowd-pleasers like pancakes, egg sandwiches, and warm pastries in a homey space. Post-breakfast, peruse eclectic galleries and vintage shops like Varga Gallery and Mystery Spot Antiques. Ultimately, though, the outdoors are Phoenicia’s main stage for everything from tubing down the Esopus to catching alfresco performances at The Phoenicia Playhouse and hiking in nearby Woodland Valley.

Big Indian

Big Indian is a true mountain hideaway, framed by rolling peaks and crisscrossed by trails that make it a natural base for hiking, especially in the fall when the foliage is at full blaze. Even the lodging here leans into the rugged setting. The 200-acre Urban Cowboy Lodge & Resort comprises the rustic-chic Lodge and several other standalone houses and cabins. The entire property combines vintage design with a playful, communal vibe—think clawfoot tubs by the window, wood-fired hot tubs, and nightly hangs in the bar.

Eastwind Oliverea Valley, by contrast, feels more Scandinavian. Its clean-lined suites and luxury A-frame cabins offer curated simplicity, fire pits, and sweeping views—the ideal setting to unplug. At the heart of the property is Dandelion, an all-day bar and restaurant serving everything from iced coffee to orange wine, along with farm-to-table fare (if it’s in season, don’t miss the ramp pesto, which has quickly become one of my all-time favorite pasta dishes).

Woodstock

Although the legendary 1969 festival actually took place in Bethel, the town of Woodstock had long been a creative haven—and that bohemian spirit is alive and well today. When I visited, most mornings began with a croissant and cappuccino from local haunts like Bread Alone Bakery. From there, we’d either lace up for the Overlook Mountain Trail, which winds past the haunting ruins of the 19th-century Overlook Mountain House, or stay local with a stroll down Tinker Street.

For the latter, that meant frequent stops at Candlestock—the candle shop famous for its whimsical, six-foot-tall “Drip Candle Mountain” and handmade beeswax creations—before flipping through vinyl at the Woodstock Music Shop. Of course, this is just the tip of the iceberg. With cafés, boutiques, and galleries all within walking distance—plus venues like the Woodstock Artists Association & Museum and the storied Bearsville Theater carrying on the town’s artistic legacy—it’s pretty much impossible to be bored here.