8 Cozy Winter Weekend Getaways from NYC

8 Cozy Winter Weekend Getaways from NYC

  • Jordan Hoch
  • 01/10/24

New York City during the holidays is aglitter with mesmerizing window displays and decor, some of the country’s best seasonal dance and theater shows, and—as anyone who lives here is well aware—lots (and lots) of tourists. As the crowds descend upon Rockefeller Center to see the Christmas tree or swarm Union Square for their holiday shopping, we don’t blame New Yorkers for pushing aside visions of sugar plums to make room for dreams of getting out of town until after the New Year.

Luckily, NYC is well-situated for many a winter weekend getaway, whether you’re craving snow-filled paradises for winter sports, charming Connecticut hamlets, or wellness meccas in western Massachusetts. We’ve combed the entire radius surrounding the Big Apple to find the absolute top-notch spots that are perfect for a quick trip away from the hustle and bustle. Just make sure you have your snow boots, flannels, and … a car. Remember those?

Read on for eight of the best cozy winter weekend getaways from New York City.

Lake Placid, New York

As a two-time home to the Winter Olympics (in 1932 and 1980), it’s hard to argue that Lake Placid isn’t the East Coast champion for snow sports. And, with the Lake Placid Olympic Center newly remodeled and reopened, this winter is an especially auspicious time to visit. Activities at the facilities include indoor and outdoor ice skating, speed skating sessions, as well as events like the Adirondack Winter Invitational for college hockey players.

But, the Center is far from the only winter sports hub in town here. The nearby Whiteface Mountain has over 90 trails spanning 25 miles and covering three peaks and is especially notable for boasting the greatest vertical drop on the East Coast. And, if that’s not enough for adrenaline junkies, you can also rocket down tracks at the Lake Placid Bobsled Experience or (in warmer months) tackle the longest mountain coaster in the USA, the heart-pumping Cliffside Coaster. After you’ve had your fill of snow and ice, you can stroll Main Street to pick up new ski gear or stock up on gorgeously scented candles and lotions from Pure Placid. We love the Mount Marcy, scented with citrus, basil, and sandalwood.

A straight shot up I-87 followed by a 40-mile stretch on NY 73W, Lake Placid is about a five-hour drive north of New York City. If you're looking to stretch your legs along the way, Saratoga Springs is an excellent stopping point: grab a hearty brunch of breakfast sandwiches stuffed with smoked applewood bacon at The Merc before you finish your drive.

Where to stay: There are few places more magical in winter than Lake Placid Lodge, a quintessential Adirondack property that features rooms with large stone fireplaces, beds made out of tree branches, and stunning views of the namesake lake. For even more privacy, you can also book one of the secluded, cozy cabins just a short walk from the main lodge. Winter activities on-site include ice skating, cross-country skiing, and snow bonfires with s’mores. Nearby Whiteface Lodge is ideal for families, thanks to year-round indoor and outdoor pools, a surround-sound movie theater, a family game room, and nightly campfires.

Kennebunkport, Maine

Most people consider this seaside getaway a summer-only destination, but Kennebunkport’s distinct charm reveals itself when the weather hardens and coastal Maine’s rugged beauty comes sharply into focus. Plus, you can head inland for spectacular cross-country skiing around the town. There are more than 20 miles of trails on the 600 acres at Harris Farm, for example, a working dairy farm that opens up its lands to outdoorsy types each winter. Don’t discount a walk on the beach either, or even a surf in the icy waters when thick winter swells fed by nor’easters beckon dedicated surfers.

It’s about a five-hour drive from NYC, mostly along I-95, but you can–and should–break up the trip with a stop in Seabrook, New Hampshire for steamed whole lobsters at Brown’s Lobster Pound.

Where to stay: The Boathouse Waterfront Hotel is the best perch year-round: as the name implies, it’s situated on the harborside of the Kennebunk River and is just steps from the town’s cute and quirky shops. In nearby Kennebunk, The Grand Hotel, an elegant, three-story building set atop Chase Hill, includes views of bustling Dock Square in the center of town. Don’t miss the on-site art gallery and its rotating selection of paintings made both by local and international artists. And those looking for both an elevated and pampering experience should make a beeline for White Barn Inn, Auberge Resorts Collection. The historic inn and private cottages feature details like fresh flowers and Prima Fleur toiletries, while the larger suites boast deep soaking tubs and—the ultimate winter indulgence—gas fireplaces.

Litchfield County, Connecticut

Gilmore Girls fans will no doubt recognize this bucolic area of Connecticut—the fictional town of Star’s Hollow was based on real-life Washington Depot. But that Rockwellian vibe wasn’t just movie magic: Many of the small hamlets here seem almost too idyllic to be real, and all are worth exploring. Imbued with that quintessential New England feel, the different towns pride themselves on their specialties. Hit up New Preston for home furnishings (we love J. Seitz & Co.); Kent for its art galleries like Kenise Barnes Fine Art and Ober Gallery; and tiny Bantam for its collection of beloved Arethusa dining spots. Plan a dinner at Arethusa al tavolo (the menu changes frequently, but do order the parsnip-date soup if you can). Whatever you do, save room for Arethusa Farm Dairy’s rightfully famous ice cream.

Since this is New England, options for winter sports abound, including Mohawk Mountain for skiing and tubing, and the 400-plus acre Black Rock State Park for cross-country skiing. Afterward, pop into Arethusa a Mano to refuel with coffee and pastries.

This tranquil stretch of Connecticut can be reached in approximately two-and-a-half hours from New York City. Take the Hutchinson River Parkway to I-684 followed by Route 7, which meanders through much of the county. Litchfield encompasses much of the northwestern part of the state, where it borders New York.

Where to stay: The most sought-after property in the region is the Mayflower Inn & Spa, Auberge Resorts Collection, a spectacular English country house featuring rooms with four-poster beds and oriental rugs. (The entire property was given a facelift a few years back by celebrated interior designer Celerie Kemble.) And while its spa has historically been one of the most beloved on the East Coast, the hotel’s partnership with THE WELL has upped the wow factor and pampering significantly (we love the signature Integrated Detox treatment). But, if you’ve ever wanted to sleep in a helicopter hangar or a treehouse, make sure to visit the wacky, but luxurious cottages at Winvian Farm. The restaurant is also worth a trip, alone: Almost all the food served in the 18th-century dining room is grown in one of three on-site greenhouses or harvested from the property’s three acres of organic gardens.

Rhinebeck, New York

Few upstate New York locales are as postcard-perfect as Rhinebeck: The Hudson Valley town’s main streets are lined with spectacular home design stores, unique boutiques selling everything from children’s toys to craft beer, and, most notably, a wealth of destination-worthy restaurants. Book a table at The Amsterdam for the best locally sourced, New American food in the Hudson Valley; Bia for innovative takes on Irish (double your order of the brown bread); and Cinnamon for Indian dishes like a murgh shahi korma as elevated and nuanced as anything you’d find in Manhattan. Music lovers will also appreciate the proximity to Bard College, home of the Fisher Center for the Performing Arts. Housed in a stunning building designed by starchitect Frank Gehry, it's worth checking out one of the many stellar classical performances.

This charming hamlet in Dutchess County is about a two-hour drive from New York City. The prettiest route up is via the winding Taconic State Parkway; don’t skip the Taste NY Market at Todd Hill as you pass through Poughkeepsie. Situated in the middle of the parkway, it’s hard to miss, all the better for stocking up on an excellent array of New York-made goods like fresh apple cider, yogurts, and jams.

Where to stay: Rhinebeck boasts the oldest continually operating inn in the country, The Beekman Arms. The property’s front lawn was actually a training ground for the Fourth Regiment of the Continental Army, who performed drills on the expansive space in preparation for the American Revolution. The historic rooms here (some are in the original inn building from 1766) are cozy with thick quilts and four-poster beds, and—fun fact—all also boast a decanter of sherry. For something more modern, check out Mirbeau Inn & Spa, a wellness-focused hotel housed in a building inspired by a classic French château. Even if you don’t book a room here, it’s worth checking out the spa, whose wide array of services includes mineral baths, massages, and seasonal treatments like body scrubs with sugar and orange peel to ward off dry winter skin.

The Poconos, Pennsylvania

This stretch of lakes and historic towns may be most famous for its plethora of summertime activities, but its location also lends itself to family-friendly skiing and other wintertime pursuits. There are over 185 trails for skiing, sledding, and tubing in the area, at spots like Camelback Mountain (home to America’s largest snow-tubing park); or Blue Mountain Resort, which has Pennsylvania’s highest vertical drop of 1,082 feet, and 40 trails of varying difficulty to please both skiers and snowboarders. But if you prefer less rigorous outdoor activities, The Poconos has you covered: Book a horse-drawn sleigh ride through Happy Trails Stables or an exhilarating dog sled tour with Arctic Paws. Or skip all the activities and simply stroll through the lovely Victorian homes converted to shops and galleries in the quaint town of Jim Thorpe.

This famed resort region is about two-and-a-half hours from New York City, reached via I-80W. You can make a pitstop at the Delaware Water Gap, right on the border of New Jersey and Pennsylvania—it has over 100 miles of scenic roadways.

Where to stay: The Lodge at Woodloch is especially cozy this time of year; winter spa treatments like the seasonal body polish with coffee soothes dry skin in need of hydration. But if you want to lean fully into the season, make sure to sample the resort’s Snow Room for a chilly blast that’s not for the faint-hearted. A more family-friendly option is Skytop Lodge, a member of the Historic Hotels of America nestled in 5,500 acres of forest. Winter activities include ice fishing, tubing, and snowshoeing.

Lower Catskills, New York

The southern Catskills are far less rural than its northern reaches, and towns like Andes and Phoenicia embody a newfound artsy edge via galleries and hip restaurants—making them particularly appealing to New York City travelers.

Andes is notable for its tightly edited collection of boutiques, including the wondrous mix of antiques and unique finds at The Tin Horn and vintage duds with a Catskills appeal at Clementine Vintage Clothing. The area is home to numerous outdoorsy pursuits, too, whether that’s the slopes of Hunter Mountain a few miles back along Route 28, or within Catskill Park's 700,000-plus acres—much of which is prime territory for snowmobiling. When you get peckish, swing by Wayside Cider, a brewhouse and restaurant that relishes in being the town’s social center on weekends.

This area is just under a three-hour drive from New York, and taking I-87 to Route 28 gives way to spectacular countryside views for miles. Plan a lunchtime arrival so you have an excuse to order the patty melt on rye at the bustling Phoenicia Diner.

Where to stay: Four artists from Brooklyn commandeered the 1940s-era motel in Phoenicia back in 2013 and rebooted it as The Graham & Co. Some of the 20 mod-rustic rooms designed with reclaimed wood and cowhide rugs have kitchenettes for a DIY-meal option. One of the newer properties in the area is also one of the chicest. Piaule Catskill brands itself as a “landscape hotel”: modern, private cabins tucked into the woods, with plenty of wellness experiences like reiki sessions, forest bathing, and massages.

Woodstock, Vermont

Centered on an English town green that’s surrounded by whitewashed houses, this manicured settlement is even prettier when blanketed in a few inches of pristine snow. Center and Elm Streets are lined with independent shops and restaurants, like the Vermont Eclectic Company, which sells T-shirts with graphic decals, all designed by Vermont-based artists (take a photo with the giant fiberglass chicken on the shop floor for the ‘gram). Also nearby is FH Gillingham & Sons, an enormous old-school general store stocked with plenty of Vermont’s finest elixir, maple syrup. And don’t miss Farmhouse Pottery on the outskirts of town—located in a former Bible bindery, the space sells everything from classic pie dishes to espresso cups and offers wheel workshops and clay dates for crafty types.

It’s less than a five-hour drive from New York to this charming southern Vermont town, via I-91 through Connecticut and the Berkshires. Detour to Brattleboro as you drive north for a quick photo pitstop: The picturesque town is home to the wooden 19th century Creamery Bridge, listed on the National Register of Historic Places.

Where to stay: There is nowhere more iconic (or photogenic) in town than the famed, white clapboard Woodstock Inn & Resort. Known as “Vermont’s Most Beautiful Address,” experiences at the hotel range from a 10,000 square-foot LEED-certified spa; a seasonally open 18-hole golf course designed by Robert Trent Jones, Sr.; and a partnership with New England Falconry for up-close sessions with birds of prey. Other top boltholes include Lincoln Inn & Restaurant at The Covered Bridge, which is nestled on a six-acre parcel of land and has half a dozen cozy rooms. Or, for the ultimate luxury stay, nearby Twin Farms provides easy access to private ski slopes, ice fishing, and fat-tire biking trails, plus uniquely designed cottages decorated with museum-quality art.

The Berkshires, Massachusetts

Though the area might be justifiably known for its superb leaf-peeping each fall, an arguably better time to visit is winter when the snow-covered hills turn into some of the best ski slopes in Massachusetts. Start by conquering the huge range of terrain at Catamount Mountain Resort, ideal for families with members of varying abilities. Butternut is another family-friendly, must-ski hub that offers ski and snowboard lessons for kids ages four and up, while there are 45 different runs (25 lit for night skiing) at Jiminy Peak in the Taconic Mountains. Not a downhill skier? No worries: Set out for Canterbury Farms’ meditative cross-country ski trails instead.

The Berkshires are also home to two of the region’s most lauded art museums: The Clark and MASS MoCA. The former, located in the art-centric hub of Williamstown (home to the famed Williamstown Theatre Festival, as well), carries an impressive collection of Renaissance to early 20th-century European and American paintings; at the latter, more modern and contemporary offerings are on view.

The most picturesque route for the drive up to western Massachusetts (around three hours) is via the Taconic Parkway, which slices through the Eastern edge of New York before taking you across state lines into Massachusetts’ Berkshires. One of the prettiest places to stretch your legs en route is Millbrook, home to rolling farms and the excellent Millbrook Antique Mall. Grab smoked salmon BLTs to go at Babette’s Kitchen after snagging a rare book or vintage earrings.

Where to stay: For an ultra-luxe wellness retreat, look into Miraval which opened its third property near Lenox three years ago. The sprawling campus is anchored by an enormous spa, of course, but the food is another lure: The all-inclusive rates allow you to graze its mindful eating menu on a whim, whether that’s made-to-order smoothies at breakfast or lobster ravioli at dinner. Day passes are available and allow guests access to all the wellness classes and spa, and also include meals. A quirkier option nearby is 33 Main, an eight-room inn owned and operated by local homeware designer Annie Selke. Cannily, Selke intended it to be as much a showroom as a hotel—many of the rooms’ items (sheets, towels, rugs) are available for purchase.

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