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Trip Ideas

Trip Matchmaker: Find Your Perfect Upstate NY Getaway

Whether you’re a nature lover or an antique hunter, adventurous foodie or adrenaline junkie, there’s an upstate New York town that’s just right for you. Leigh Crandall shares seven ideal weekend itineraries for all types of travelers

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For Road Tripping Friends: Woodstock & Phoenicia

Woodstock has retained the funky vibe that made it famous in the 1960s. Spend an afternoon on the main drag, Tinker Street, browsing the boutiques and galleries—one of our favorite stops is the Woodstock Artists Association & Museum, where you'll find exhibits dedicated to work by area artists. Check into the recently opened Hotel Dylan, a hip 11-room boutique with fun in-room extras like Crosley record players and an assortment of vinyl, beach reads and games like Trivial Pursuit. For dinner, head just up the road to Italian restaurant Cucina, a lively local favorite housed in a former farmhouse. After dark, cozy up in an Adirondack chair around one of the Dylan’s fire pits. The next day, get an early start and drive up Route 28 to Phoenicia for a breakfast of biscuits and gravy at the town’s well-loved diner. Work off your meal with a hike to Kaaterskill Falls, a picture perfect two-drop waterfall, then meander your way south, saving time to pop into some of the 14 wineries along the Shawangunk Wine Trail.

Check Prices for Hotel Dylan in Woodstock, NY

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For History Buffs: Hyde Park & Rhinebeck

If the words “George Washington slept here” appeal, then your home base for this weekend is the circa 1766 Beekman Arms in Rhinebeck, America’s oldest operating inn, where Washington did indeed stay (as did Alexander Hamilton, Franklin Roosevelt and, more recently, the majority of Chelsea Clinton’s wedding guests during her 2010 nuptials). This region is particularly well known for its historic mansions—in Rhinebeck the Queen Anne-style Wilderstein Historic Estate offers a peek into the lives of Gilded Age aristocracy, while Hyde Park is home to the sprawling Vanderbilt Mansion and The Home of FDR. For dinner, make a reservation at American Bounty, the award-winning restaurant at the Culinary Institute of America in Hyde Park, which celebrates its 30th anniversary this year. End your night with a pint at the cozy Liberty Public House back in historic Rhinebeck, housed in the circa 1860 Starr Institute.

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For the Sportsman: Millbrook & Saugerties

Begin your trip with a visit to Orvis Sandanona in Millbrook, one of the top game lodges in the country. Opt for a round on their 20-stand sporting clay course or sign up for their day-long fly-fishing or wingshooting schools. Next, head north to Diamond Mills in nearby Saugerties, a former paper mill turned hotel positioned right on Esopus Creek Falls, visible from each room’s private balcony. Rent a pair of wheels from Revolution Bicycles on Main Street and take a self-guided tour along the Saugerties Historic Village Bike Route, which takes peddlers past sights like the circa 1869 Saugerties Lighthouse and Carnegie Library Building. Or, see the sites from the water with I Paddle New York, which offers tours of the Esopus Bend Nature Preserve and more via kayak. For a photo-worthy hike, rise early and hit the trails of Falling Waters Preserve, which takes visitors along the banks of the Hudson. When hunger strikes, head to Miss Lucy’s Kitchen for farm-to-table comfort food like Hudson Valley duck and house smoked BBQ ribs.

Check Prices for Diamond Mills Hotel & Tavern in Saugerties, NY

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For Art Lovers: Beacon & New Windsor

New Windsor is home to Storm King Arts Center, an outdoor sculpture park where the landscape is every bit as beautiful as the artwork positioned across its 500 acres. First time visitors should opt for the free tram ride, which offers a 30-minute overview of the park’s permanent collection. Or explore the park on your own via bike. The center offers bike rentals on a first come, first served basis for $8 per hour, and rentals include a map of the bike routes, which crisscross the park’s hills, fields and woodlands. Next, head northeast across the Hudson to the riverside town of Beacon, where you’ll find Dia:Beacon, a museum housed in a former Nabisco box printing factory that now displays work from modern artists like Richard Serra, Blinky Palermo and Agnes Martin. The town also hosts Second Saturdays each month, when galleries and shops along Main Street stay open until 9 pm. Spend the night at the Roundhouse at Beacon Falls, a boutique sleep situated along Fishkill Creek. Dine at the hotel’s Swift restaurant for seasonal, local fare paired with a stunning view of Beacon Falls.

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Photo by Jen Munkvold

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For Food Fans: Milton, Pound Ridge & Pocantico Hills

Start you weekend with a stay at Buttermilk Falls Inn & Spa, a 75-acre estate situated along the Hudson River in Milton. Unwind at their spa, where ingredients from the inn’s garden and beehives are repurposed into massage and wrap treatments. Stroll their working farm in the afternoon, then make a dinner reservation at Buttermilk’s Henry at the Farm restaurant where the farm's fruits, vegetables and herbs are fashioned into New American dishes. The next day, drive south to the Inn at Pound Ridge by celeb chef Jean-George Vongerichten, where brunch dishes like Croque M (Niman Ranch ham, comté and Gruyere cheese) are served in a converted 1833 inn. End the trip with a visit to the Stone Barns Center for Agriculture, an 80-acre nonprofit farm center in Pocantico Hills. Visitors are free to stroll through the pastures and barnyards where you’ll see sheep, turkeys and chickens, wander the woodlands to visit the Berkshire pigs’ paddocks and chat with the farm’s workers. Much of the produce and livestock raised on the farm is used at the center’s Blue Hill at Stone Barns, one of the region’s top restaurants. Reservations are tough to get, but if you arrive right when the doors open at 1pm on Sunday, you’ll be able to grab a seat at the walk-ins only bar where an abbreviated tasting menu is offered for lunch.

Check Prices for Buttermilk Falls Inn in Hamilton, NY

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For Antique Hunters: Hudson

Hudson’s Warren Street is a treasure trove for travelers who love the hunt for antique furniture, vintage clothes, jewelry and collectibles. First-time visitors can start with a stop at the Hudson Antique Dealers Association for a lay of the land, which includes over 60 businesses in the area. If you prefer the action of an auction, check the calendar of Stair Auctioneers & Appraisers, which hosts monthly events for items with values under $2,000. For breakfast on Saturdays, stroll the Hudson Farmer’s Market on the corner of 6th and Columbia featuring baked goods and produce from the region’s farmers and food producers. A best bet for dinner is Fish & Game, where farm-to-table fare is served in a beautifully renovated 19th century blacksmith’s shop. For a drink, visit the Spotty Dog Books & Ale, which is part bookstore, part bar. Rest up at The Hudson Milliner, a cozy guesthouse right on Warren Street, where guest rooms are decorated with a whimsical mix of industrial furniture and antiques.

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For Families: Lake Placid

The site of both the 1932 and 1980 Olympic Games, Lake Placid now hosts a wide range of athletic activities open to the public. Go ice skating at the Olympic Center, wind your way down the track in a bobsled or try your hand at the wheeled luge. It’s also worth a visit to the Olympic Ski Jump Complex to watch the next generation of athletes in training. During the winter, dog sledding is offered at Mirror Lake as is tubing and tobogganing. Save time to hike the gorges of Ausable Chasm in nearby Keeseville, which can be explored by river raft or on foot. Check the calendar at the Lake Placid Center for the Arts for kid-friendly performances throughout the year and, for a sweet treat, visit the 1950s-themed ice cream parlor Emma’s for maple cream soft serve.