Weekend Getaway from NYC in Winter: Top Reviews

New York ‘The Big Apple’ City ranks quite high on the lists of many travelers lists for the holiday season, and it’s not surprising. Between twinkling holiday markets, the smell of crackling profiteroles, and Rockefeller Center’s Christmas tree, there’s so much to do and see here. However, there are times we felt like getting away from the city during winter, and this goes for locals too. Luckily, there are many a winter weekend getaway from NYC in winter due to the city’s unique location. Whether we wanted to head south to the rolling, undulating scenery of Virginia or north to the stunning and cozy Adirondacks, we had destination options galore to get out of NYC during wintertime.

Not just that, but we could choose destinations depending on how far we’d like to travel, whether by road, rail, or even flight, the climate we prefered, and our favorite kind of activities. Plus, the very reasons that drew considerable crowds to NYC are often the impetus for people to enjoy weekend getaways from it. Here’s a guide to visiting the best destinations close to New York City for a wintertime getaway.

Philadelphia, Pennsylvania

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We begin with one of the best year-round escapes from NYC, Philadelphia, which sits just 95 mi (153 km) southwest of Manhattan. That being said, “The City of Brotherly Love” gives the Big Apple a run for its money when it comes to winter. During snow season, check out sights like Deck the Hall Light Show at Dilworth Park’s Wintergarden, the Holiday Light Show at Shady Brook Farm, and the Electrical Spectacle at Franklin Square.

Beyond the lights and the sights, a trip to Athens of America is incomplete without enjoying a good cheesesteak: tourists love Geno’s or Pat’s, while local favorites include Campo’s Deli or John’s Roast Pork. Aside from its fame as a high-end culinary destination, did you know that Philadelphia’s City Hall’s Reading Terminal Market is the oldest farmers’ market in America? Yep.

If you’re traveling with the kids, stay at The Logan, Curio Collection by Hilton, one of the best family hotels in Philadelphia. The plush hotel has excellent and spacious modern rooms, a rooftop terrace, a steakhouse, and a full-service spa, a steakhouse, and a rooftop terrace.

Bermuda, British Overseas Territory

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Plot twist: Weekend getaways don’t just need to be a drive away, do they? We’re talking about Bermuda, baby! Despite not being within driving distance, it’s actually a shorter commute from NYC than many places on this list, with a two-hour flight landing you in this subtropical paradise.

Winter in Bermuda is very different as compared to the other destinations on this list. It’s all about drinking rum Swizzels and other cocktails, swimming in the crystal-clear waters of the North Atlantic Ocean and basking in the sun. There were a ton of other interesting activities we indulged in, like visiting natural wonders like the Blue Hole Park. We even made our own scent at the Lili Bermuda Perfumery!

Combine history and luxurious island living at the Cambridge Beaches Resort & Spa, a 100-year-plus property. It retains much of its original architectural touches, but added modernity in the form of a full-service spa, many sports courts, outdoor and indoor pools, four private beaches and modern sea-facing rooms.

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Nantucket, Massachusetts

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It’s a seven-hour drive and ferry ride away, but it’s worth it. We’re talking about Nantucket, Massachusetts, which is also an 80-minute flight away if you don’t want to drive and ride the ferry.

However, no matter how you arrive, this pure slice of Americana is all about relaxation and rejuvenation, even in winter. One of the most popular things to do is the Christmas Stroll event, which is an entire weekend of fun events, Santa’s arrival by boat, caroling, and holiday markets. As we walked around town, we got to admire the stunning holiday decorations on the Instagram-worthy shingled homes. What’s more, we also got to explore some sights that are year-round, like the Whaling Museum and the lovely beaches. When we wanted to get out of town, we headed to the three lighthouses along the coast, each of which are special and unique.

The cherry on top of our serene Nantucket vacation was staying at one of Nantucket’s best boutique hotels, the White Elephant Hotel. Elegantly appointed sea-facing rooms aside, the hotel also has a fabulous fine dining restaurant, a harborside terrace, and the White Elephant Spa.

Litchfield County, Connecticut

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If you’re a “Gilmore Girls” fan, then you’ll definitely recognize the bucolic Litchfield County of Connecticut, which is where the fictional town of Star’s Hollow was based. However, the vibe of the town wasn’t just onscreen magic; many of the county’s small hamlets are almost too idyllic to be real, and they’re all worth exploring.

Besides all that quintessential New England feeling, the towns all have their own specialties. For instance, Bantam has Arethusa dining spots and Kent is known for its art galleries. Also, whatever you do, do not miss digging into the rightfully famous ice-cream of Arethusa Farm Dairy. Also, since this is New England, there are multiple options for winter sports. We went cross-country skiing at the 400-acre-plus Black Rock State Park and Mohawk Mountain for tubing and skiing. The tranquil Litchfield County sits in the northwestern part of the state, bordering New York, can be reached in around 2.5 hours from NYC along I-684 and Route 7.

It’s no doubt that the only place to stay in this part of Connecticut is the Mayflower Inn & Spa, Auberge Resorts Collection. This spectacular English country house-turned-four-star hotel boasts drop-dead gorgeous rooms with four-poster beds, sleek mod-cons, and luxurious spa-like bathrooms. Moreover, the hotel also has one of the best spas on the East Coast, making it one of the most romantic hotels in Connecticut.

Boston, Massachusetts

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Escaping one city could also mean heading to another city, like we did when we escaped from NYC to Boston, a.k.a. Beantown, a.k.a. the Cradle of Liberty. Since we’re outright history buffs, we were more than happy to make the four-hour journey north to exploring one of the most patriotic places in the United States. We walked down the famed “Freedom Trail,” starting with the statue of George Washington at the Boston Common and ending at the world’s oldest commissioned warship, the USS Constitution. The Isabella Stewart Gardner Museum was another fantastic destination, as was the Institute of Contemporary Art.

There’s something for sports fans also in Boston: you can catch a thrilling Red Sox game at Fenway Park. Are you a true culture vulture? Head to Faneuil Hall Marketplace, one of the top USA attractions for tourists.

Since we were on a historical winter vacation in Boston, we decided to stay at The Bostonian Boston. One of Boston’s historic hotels, it’s also the city’s first historic hotel and also one of its most sought-after ones. Its location aside, the hotel boasts modern rooms, a 24-hour fitness center, concierge services, a restaurant and a bar, and even on-site spa services.

Montreal, Canada

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Are we really including a place from a whole other country as a weekend getaway from New York City? Yes, we are! Folks probably forget that Montreal is a quick six-hour drive from NYC, allowing you to immerse yourself in not just another country, but also culture and cuisine. The culinary capital of the country and one of the most visited Canadian cities, Montreal actually opens up in wintertime. In fact, the winter season kicks off with Christmas markets, like the huge Christmas Village at Atwater Market. Secondly, there are many, many festivals you can attend, like the Igloofest and the multi-week Montréal en Lumière.

What’s more, winter is maple syrup season, which means you can savor many treats centered around Quebec’s sweetest natural resource. Plus, there are a whole lot of comfort foods like Joe beef, poutine, and more. Wintertime waterfront scenes are another forte, whether you want to revitalize at the winter hot spa Bota Bota or walk along old-Montreal port. Did we mention there’s skiing and ice skating for adventurous vacationers on the Mont-Royal? Yep.

If you want to indulge, we’d highly recommend Fairmont the Queen Elizabeth in Downtown Montreal. One of Montreal’s best hotels, it’s also the city’s first luxury hotel and the place of John Lennon-Yoko Ono’s famous 1969 bed-in. Despite the refurbished digs, the hotel still drips in midcentury glamor, from the hallways to the restaurant and common areas.

The Poconos, Pennsylvania

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The stretch of historic towns and lakes that make up the Poconos might be most famous for being a summer destination. However, the region takes on a different, radiant glow during wintertime, complete with skiing and other snowy pursuits. Some of the best ski resorts in the Poconos, like Blue Mountain and Camelback resorts, boast more than 185 trails for tubing, sledding, snowboarding, and skiing. In fact, Camelback has the largest snow-tubing park in the country, while Blue Mountain is home to the highest vertical drop (1,082 ft) in the state.

If you prefer more laidback activities, there are also dog sled tours and horse-drawn sleigh rides. Don’t miss strolling through the lovely towns like Jim Thorpe and soaking in the lovely Victorian homes-turned-galleries and shops. The best bit? This famed resort region is just over 2.5 hours from NYC via the I-80 West.

So, where to stay in the Poconos? We highly recommend The Lodge at Woodloch in Hawley, one of the most romantic hotels in the Poconos. Especially cozy during winter, this romantic destination boasts a ton of amenities like a heated outdoor pool, couples’ massages and winter spa treatments, a romantic restaurant, equally amorous digs, and even a Snow Room!

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Woodstock, Vermont

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Five hours from NYC lies the magical 18th-century-founded Vermont shire town of Woodstock, which is centered round an English green and flanked by whitewashed homes. Does it feel manicured? Yes, but in a natural, pretty way which was even prettier when swathed in pristine snow. We visited during the wintertime Wassail Weekend, the annual December celebrations with a parade and many other activities, like tree lighting. Moreover, Woodstock is also home to some of the finest, oldest general stores in the country, like the FH Gillingham & Sons. We picked up many local goodies like handicrafts, jams, and jellies. They even sell Vermont’s finest elixir, maple syrup!

There are a few unmissable things on the outer fringes of the town too, like the dairy-producing Billings Farm & Museum, Farmhouse Pottery, and the Rockefeller National Historical Park. Do you love winter adventures? Look beyond the name and head to the Suicide Six skiing and snowboarding area. While there is no dearth of swish resorts in the region, we loved staying at the bolt hole that is the Lincoln Inn & Restaurant at The Covered Bridge. Tucked on six acres of land, this secluded restaurant-inn had six rustic and unique rooms, along with a destination-worthy eatery.

Not for nothing is Woodstock one of the best places to visit and things to do in Vermont.

Lower Catskills, New York

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If you’re thinking why head to the rural NY in winter, think again. The Lower Catskills are far less rural than the northern reaches, with picture-perfect towns like Phoenicia and Andes turning wonderlands with a fresh covering of snow. In fact, Phoenicia is a summer favorite for Brooklynites, but during wintertime, it’s a fabulous destination with oodles of small-town charm. The same goes for Andes, which boasts a newfound artsy edge with tons of hip restaurants and galleries on the main drag, making it especially popular with hip NYC travelers.

That’s not all; the region has a plethora of outdoorsy pursuits, too. This included the premier skiing destination in the region, Hunter Mountain, which has a stunning 1,600-foot vertical drop and miles and miles of skiing trails. What’s more, there’s also the 700,000-acre-huge Catskill Park, which is prime territory for snowmobiling. With the region being a less-than-three-hour drive from NYC, we’d planned a lunchtime arrival and headed straight to the bustling Phoenicia Diner, where we gorged on patty melt on rye.

We were fascinated by Piaule Catskill, one of the region’s newer properties and also one of its chicest. This “landscape hotel” featured private, ultra-modern, and mind you, luxurious cabins tucked into the woods. It also had lots of wellness experiences like massages, forest bathing, and reiki sessions, as well as a spa and a restaurant.

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Kennebunkport, Maine

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The seaside Kennebunkport is a popular summer destination, but it also happens to be where the best fall foliage in Maine is. Not just that, but the town’s distinct charm actually emerges when the weather turns cold, with coastal Maine’s rugged beauty coming to the fore. During winter, the town transforms into a wonderland, with spectacular cross-country skiing trails, like the 20 mi (32 km) of trails at the 600-acre-huge working dairy that is Harris Farm. If you think it’s too cold to walk on the beach, then bundle up, but don’t miss it. Heck, we even saw enthusiastic and dedicated surfers taking on the icy waters when the thick winter swells came in. The best bit? Kennebunkport is a five-hour drive from NYC, with the route mostly being along the I-95.

While there are many year-round perches and grand, historic hotels in the town, we loved staying at the Inn at English Meadows, one of the best B&B in Kennebunkport, Maine. This elegant yet historic B&B boasted a fantastic culinary experience, including breakfasts and evening receptions. Not just that, but also the 12 rooms and suites were dreamy to the hilt, with huge windows, seating areas, and even gas fireplaces. Sigh.

Lake Placid, New York

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We’d only ever heard of the horror movie until we visited Lake Placid. However, it was love at first sight with the stunning town, a two-time home to the Winter Olympics and a year-round outdoor destination. Located five hours from the Big Apple, this place is all about a dazzling array of outdoor winter activities. Think outdoor and indoor ice skating, winter hiking through the High Falls Gorge, skiing/snowboarding on the 25 mi (40 km) of terrain on the slopes of Whiteface Mountain, and speed skating. Of course, there are also events such as the Adirondack Winter Invitational for college hockey players.

When we’d had our fill of ice and snow, we’d stroll down Main Street to stock up on scented lotions and candles or grab a delicious lunch of pulled pork, ribs, and brisket. On days we didn’t want to eat breakfast at our accommodations, the Breakfast Club was the place to be. We’d make our way through hearty decadent French toast fondues, breakfast sandwiches, and all sorts of egg dishes.

There was no dearth of stunning resorts and B&Bs in the region, but we particularly loved the
Mirror Lake Inn Resort & Spa. One of Upstate New York’s best boutique hotels, it sat just five minutes from downtown Lake Placid. The stunning hotel boasted elegant lake-view digs with four-poster beds, fireplaces, and private balconies. Besides a slew of organized activities – think everything from sunset cruises and guided snowshoe hikes to yoga classes – the resort also had a lovely pool, three restaurants, and a decadent full-service spa.

What winter destination cities are three hours or less from NYC?

A majority of the places on this list are less than three hours from NYC, including Litchfield County, the Poconos, Woodstock, Lake Placid, and Philadelphia as well.

What is a good road trip from New York?

While there are many excellent road trips, our favorite is Lake Placid, which is a five-hour drive away.

Where is the best skiing in Christmas near NYC?

Some of the best places are Camelback in the Poconos, Pennsylvania and Belleayre and Hunter Mountain in the Catskills.