Your Perfect Catskills Vacation: Where to Stay and What to See

Phoenicia Diner, Phoenicia, NY

The Phoenicia Diner has all the trappings of our most adored greasy spoons: swiveling chrome bar stools, Formica tables, linoleum flooring, paper placemats with local advertisements, and an all-day breakfast menu. Add a slightly hipster vibe à la Wes Anderson's Moonrise Kingdom to the whole dynamic, and we can't get enough. Fuel up for a day of exploration with "farm-to-counter" food like the grass-fed roast beef sandwich, topped with cheddar, caramelized onions, watercress, and house-made horseradish mayo.

Brushland Eating House, Bovina Center, NY

Bovina is as pastoral as American towns come—just look to the hamlet's bounty of rambling hills and farm stands, not to mention a frozen-in-time Main Street set against a striking Catskill Mountains backdrop. Roll up to Brushland, a combined restaurant and boutique stay (see: Above Brushland and Behind Brushland—both are Country Living cover-worthy), for the best meal around. Classic comfort foods like burgers, cast-iron chicken, pork schnitzel, and hand-rolled pasta are given a contemporary update and arrive plated on dainty, gold-rimmed porcelain.

Table on Ten, Bloomville, NY

Unfussy, farm-to-table dining is what Table on Ten does best. The part-café, part-Italianate–style inn plants its roots in Bloomville, a tiny upstate town with less than 250 people, and encourages socialization with communal picnic tables. Grab a seat out back under trees draped in string lights and order up one of their savory wood-fired pizzas (we're partial to the marinated fennel pie with preserved meyer lemon, feta, and parsley). Before you hit the road, support small businesses (and your belly's continued happiness) with a purchase of local coffee, syrup, raw honey, or granola from the onsite shop.

Peekamoose, Big Indian, NY

When Peekamoose owners Devin and Marybeth Mills converted an old farmhouse in Big Indian into humble country kitchen, they did so with quite a bit of know-how. That's because the pair had already cut their teeth in a few of NYC’s most impressive institutions (see: the Hudson River Club, Le Bernardin, Gramercy Tavern, etc.) It's all about the freshest ingredients at Peekamoose—"silly name, serious food"—whose daily revolving menu relies on local growers. Split a starter before digging into specialties like the wood-grilled pork tenderloin with rainbow Swiss chard, fennel confit, and grilled peach and watercress.

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Scribner's Catskill Lodge, Hunter, NY

A bespoke mountain lodge for the urban explorer, Scribner’s mixes a minimalistic aesthetic—vintage rugs, custom-built furniture, rustic-chic details—with 20 acres of mountainside for skiing or hiking (depending on the weather) right outside its front door. Planning on spending a night in? Dine on the cedar deck at onsite Prospect Restaurant and Bar, which serves local cuisine around a fire pit.

The DeWitt Oak Hill, Oak Hill, NY

Hugging the banks of Catskill Creek, eclectic DeWitt Oak Hill is a four-room inn brimming with antiques curated by proprietors Dorothée and Diane. Relax in the two-story great room—we suggest grabbing an art book and trying the Hollywood Regency curved velvet sofa on for size—or retire to your minimalist, individually decorated digs. Fancy the mid-century modern desk in your room or brass wall sconces in the hall? Almost every piece in the inn is for sale via French & Scouser, the duo’s vintage furniture business.

The North Branch Inn, North Branch, NY

Antique stores, farmers markets, and roaring bonfires are Sullivan County’s bread and butter. Make the North Branch Inn, an early 20th-century homestead, your base for a weekend spent in the countryside. Parlors are kept homey with cast-iron stoves, mid-century modern chairs and sofas, and eclectic accents (like rooster wallpaper, antique typewriters, and shag pillows), while 14 guest rooms spread across three buildings are just as country cozy with their clawfoot tubs, fluffy white duvets, and lots of natural light. It's easy to stay busy, what with all there is to do outside, but don’t miss out on the inn’s two-lane wooden bowling alley.

Hotel Dylan, Woodstock, NY

You'll find a distinct hippie-meets-hipster vibe at Hotel Dylan. Located in Woodstock, the 11-room boutique works in a funky aesthetic with yarn-bombed nightstands, bold area rugs, playfully patterned wallpapers, and Crosley record players (pick up your vinyl at the front desk). Design details aside, the property also pleases with its enviable address on Route 28, the gateway to the 700,000-acre Catskill Park and the base of Overlook Mountain and just a hop and a skip from Phoenicia and Saugerties.

RELATED: The Hamptons Has Nothing on These Bucolic Upstate New York Stays

HiLo, Catskill, NY

Café, bar, art gallery, performance space—HiLo, a Catskill village haunt that hosts intimate concerts, indie film nights, and art installations from up-and-coming local artists, is all of these things combined. It's worth swinging by during the day for a cold brew and pesto focaccia sandwich with egg and goat cheese, but make sure you circle back at night for artisanal house cocktails like the Rip van Drinkle (Bulleit bourbon, Ancho Reyes, and bitters on the rocks) and the Vow of Silence (tequila, chartreuse, Luxardo maraschino liqueur, and lime).

Union Grove Distillery, Arkville, NY

If spirits are more your thang than beer or wine, drop by "farm licensed" craft distillery Union Grove (named for a Catskills town now lost under the Pepacton Reservoir) for a taste of their house-made Vly Creek Vodka. The copper top bar in the spot’s tasting room and cocktail lounge is the perfect place to sip the 80-proof alcohol, distilled from apples, wheat, and pure Catskill Mountains water. Interested in the science of distilling? You can also join a tour to get a behind-the-scenes look at the production process.

The Bull & Garland, Hobart, NY

Husband-and-wife duo Oliver and Melissa Pycroft are to thank for this English-style pub and inn in Hobart, a tiny town (of less than 500) on the western edge of the Catskills, whose central Main Street location draws a fair amount of locals into its cozy converted house and atmospheric outdoor space. Adirondack chairs and picnic tables fill the backyard beer garden, which often hosts local musicians, while a drink menu with local IPAs and handcrafted cocktails (think honey and sage whisky sours, lavender gin mojitos, and peach margaritas) make challenging friends to a game of pétanque that much more fun.

Catskill Scenic Trail, Stamford, NY

One of the Catskill region's greatest allures is its breathtaking natural landscape. One of the best ways to take in the area’s fertile farmland and forests is during a leisurely hike, bike, or horseback ride along the Catskill Scenic Trail. The 26-mile recreational path runs through Bloomville, South Kortright, Stamford, Hobart, Grand Gorge, and Roxbury, so you can make as many pit stops for lunch and window shopping as you see fit.

Nest, Narrowsburg, NY

In 2006, Anna Bern—previous art director of W and design director of Vogue—took her style savvy to the Catskills and opened Nest, a lifestyle boutique, and Nest Inn, a converted 1850s farmhouse lodging. After perusing the hand-crafted treasures in the store (Moroccan pom pom blankets, handwoven caftans, and cast brass rings were just a few of the wares that caught our eye), we’re certain you won’t be going home empty-handed.

Shawangunk Mountains Scenic Byway, New Paltz, NY

Shawangunk Ridge, affectionately known as “The Gunks,” extends from New Jersey to the Catskills in a show of unexpected (for the area) biodiversity—think mixed-oak forests, pitch pine-blueberry peat swamps, and deep limestone caverns. You can cover 88 miles of the region during a ride along the Shawangunk Mountains Scenic Byway, which runs through the Rondout and Wallkill valleys, various historic sites (including early Dutch settlements), and more than 30,000 acres of nature reserves.

Opus 40 Sculpture Park & Museum, Saugerties, NY

If you’re already a fan of other upstate sculpture parks and modern art museums like Dia:Beacon and Storm King Art Center, then you’ll appreciate Opus 40 just as well. Established in 1938 by Harvey Fite, founder of the Bard College Fine Arts Department, the 70+ acre sculpture park and museum centers on his most monumental work—a labyrinthine bluestone quarry/sculpture known as Opus 40. The six-and-a-half-acre fitted stone structure traverses ramps and terraces, and parts of its pathway are even subterranean. Once you’ve taken it in, drop by the blacksmith shop and Quarryman’s Museum, which house the indigenous tools he used to fashion it all.

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With charming country inns, sweeping Adirondack views, mom-and-pop antique shops, quaint farm stands, and a whole lot of fresh air, the Catskills are as no-frills as a destination can be when it comes to fashion. Our look maximizes comfort—first and foremost—with a flouncy shirt dress that's complemented by laid-back bohemian additions like a silk bandana, faux-leather crossbody bag, and chunky clogs.