Outdoor Weekend Getaway in Woodstock and the Catskills

  • Distance from Boston: 104 miles
  • Best time: Year Round
  • Best for: RomanticArts and CultureOutdoor

Say "Woodstock" and the legendary Summer of Love concert (actually held in a field in nearby Bethel, New York) immediately springs to mind. Visit the town of Woodstock, one of the Catskill Mountains best-known enclaves, and you'll be able to enjoy not only remnants of the late-'60s hippie era, but also a thriving arts scene, a robust culinary revival, and access to outdoor activities from hiking and kayaking to skiing. Meanwhile, nearby Saugerties is transitioning from sleepy to chic with the addition of a new luxury hotels and restaurants headed by chefs who've relocated from New York. Summer and fall (when weekend concert series and arts festivals up the liveliness quotient) are optimal times to visit these Ulster County towns, but cozy inns and eateries serving hearty fare make even the colder months enjoyable. For an artsy, neo-retro weekend in the mountains, here are our favorite spots to eat, play, and stay. – By Donna Heiderstadt


Woodstock and Catskills Cheat Sheet

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1Get into the laidback Catskills vibe as you browse the eclectic shops and galleries along Tinker Street and Mill Hill Road in Woodstock, such as Loominus for luxe hand-woven chenille scarves and throws, Candlestock for unique beeswax candles and a peek at its forty-year-old "drip candle mountain," and the Woodstock Artists Association Gallery & Museum.

2Head to the Creekside Grille at the Woodstock Golf Club to enjoy sunset cocktails overlooking the greens and a babbling creek.

3Walk across the street to the yellow clapboard farmhouse that's now Cucina, where the modern Italian menu of fresh seasonal ingredients can be enjoyed on the atmospheric porch in summer or next to a roaring fire in winter. Dishes may include a warm asparagus, snap pea, endive, and avocado salad with truffle vinaigrette or pork tenderloin with sage, prosciutto, and semolina gnocchi.


1Enjoy breakfast at Café Mezzaluna in Saugerties, a vibrant "bistro Latino" filled with artwork and music, where great coffee complements morning specialties such as strawberry-banana pancakes. If kayaking or hiking, order sandwiches to-go to tide you over during your activities. Alternatively, in Woodstock, you can enjoy excellent coffee and generously sized breakfast burritos and more at Bread Alone.

2Take advantage of the gorgeous natural surroundings. In summer or fall, hike 1-mile trail to Kaaterskill Falls, the highest two-tiered cascade in New York, or kayak the Hudson River with Atlantic Kayak Tours, which offers paddles for beginners to experts. In winter or early spring, cross-country ski at Mountain Trails Cross Country Ski Center in Tannersville, where you can traverse 22 miles of groomed trails, or downhill ski at nearby Belleayre (fifty-five trails and eight lifts) or Hunter (fifty-five trails and eleven lifts) mountains. Both ski areas also offer summer adventures, including mountain biking at Belleayre and ziplining at Hunter.

3Slip in another moment of rural reverie with a 75- or 90-minute warm stone massage, using heated basalt river rocks and Native American traditions, at the River Rock Health Spa.

4For dinner, reserve a table at Joshua's Cafe, where the Mediterranean-influenced menu (Greek, Moroccan, Middle Eastern) is not only flavorful, but also offers plenty of vegetarian options.

5Woodstock offers an array of performance and exhibition venues, and depending on your artistic or musical interests, you can check out the schedules at the following: Woodstock Byrdcliffe Guild, where you can enjoy contemporary art exhibits and classical music performances; the Bearsville Theater, for indie and alternative music; and the Woodstock Playhouse, for summerstock musical theater. If you're visiting in late spring, join the festivities at Mountain Jam, the annual four-day rock extravaganza.

6Wander over to the Woodstock's retro Colony Cafe, with its circa 1929 ballroom, for one last cocktail and/or dessert. Tip: It's cash only.


1Relax and people-watch over Sunday brunch at Woodstock's streamside The Bear Cafe, where chef Eric Mann serves up an array of classics, from eggs benedict to Hudson Valley duck confit.

2Browse for antiques at the Saugerties Antiques Center (220 Main St., 845-246-8234), which has twenty vendors under one roof, or at the Antiques Barn in New Paltz.

3For one last stop, don't miss cozy gastropub The Dutch Ale House to sample from fifteen craft beers on tap alongside casual grub like a bacon, egg, and cheese burger with a side of fries.

Where to Stay

If you're on a budget but still want a cozy, upscale ambience, book one of the smaller rooms at The Woodstock Inn on the Millstream (rooms from $143/night). It may look like a motel from the outside, but inside, the eighteen rooms are full of elegant, antique charm—plus there's air conditioning, cable TV, and free Wi-Fi.

In Saugerties, the luxury boutique Diamond Mills Hotel & Tavern (rooms from $250/night) is the Catskills' sleekest property. Set atop the scenic falls of Esopus Creek, its thirty rooms offer contemporary elegance with a soothing palette of pale blue and taupe, king-sized beds with fine linens, and iPod docking stations.

When to Go

The Catskills, and Ulster County in particular, is a year-round destination.

The fall harvest period is a great time to go pumpkin or apple picking or to enjoy the Taste of New Paltz food festival (mid-September) and the Hudson Valley Garlic Festival (late September).

Winter is all about the slopes (the area has three ski mountains: Belleayre, Hunter and Windham). Cut-your-own Christmas tree farms and holiday markets add a festive touch.

Spring blossoms with picturesque babbling brooks, wildflowers, and the heady revelry at the annual TAP New York Craft Beer & Fine Food Festival (last weekend in April) at Hunter Mountain.

How to Get There

By car from New York City: Neighboring Woodstock and Saugerties are 90 minutes from New York City. Take the New York State Thruway (Interstate 87) North to Exit 19 Kingston. Head west on Route 28 toward Pine Hill. After 6 miles turn right onto Route 375 and drive 3 miles to Woodstock. Saugerties is fifteen minutes east along Route 212.

By bus: While it's advisable to travel by car to best explore the towns, you can also get to Woodstock from the Port Authority Bus Terminal on Adirondack Trailways. The trip takes two and a half hours.

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