Is there anything cozier than sitting in front of a wood-burning fireplace as the snow falls outside? Sipping hot chocolate (or a hot toddy!) after a day enjoying winter sports? These idyllic scenes are not just the stuff of holiday movies but can be found within a day’s drive of Boston or New York City. There are world class ski resorts, historic inns, and exciting cities with much to offer the winter visitor. I’ve lived in New England most of my life and, though I have my favorite destinations, I’m always happy to explore. I reached out to some of the top travel writers for their suggestions for fun and romantic winter getaways in the Northeast. Read along with me to find a new snowy spot to enjoy.
Welcome to my corner of the U.S.!
Winter in the U.S. Northeast
Note: Though the Northeastern region of the United States extends all the way across Pennsylvania to the Ohio border, I’ve limited my focus to New England and New York. The destinations in this post can be reached in a days’ drive from Boston or NYC.
Winter weather in the Northeast is variable.
- Temperatures and precipitation vary widely with elevation. Expect colder weather and more snow in the mountains. Pack the essentials for a winter getaway to be prepared for all conditions.
- December can be mild with many days when you’ll only need a light jacket.
- January and February are cold, with January being the snowiest month throughout the region.
- In March and April there will be the occasional mild day but skiing and snow sports are still great in the mountains.
Examples of Average High and Low Temperatures (°F) Source: NOAA
| December | January | February | March | |
| Boston, Massachusetts | 42° / 28° | 37° / 22° | 39° / 24° | 46° / 31° |
| New York City, New York | 44° / 31° | 39° / 26° | 43° / 29° | 52° / 36° |
| Portland, Maine | 37° / 20° | 31° / 13° | 31° / 13° | 42° / 25° |
| Stowe, Vermont | 23° / 8° | 17° / 2° | 19° / 4° | 27° / 13° |
The Northeast is unusual in having a wide variety of opportunities within a small region. Most people know about the summer beaches and autumn foliage destinations, but even in the winter there’s much to do.
If you’re traveling as a family, there are outdoor recreation opportunities and indoor waterparks. Look for the ☃️ designation of family specific destinations.
Couples can enjoy lazy days (and those storied fireplaces) at most of these destination. But look for the ❤️ designation for especially romantic getaways. (Travel and Leisure lists Newport, Kennebunkport, and Stowe among New England’s Most Romantic Towns)
Skiers and snow sports enthusiasts probably already know about many of the amazing ski towns in the Northeast. The White Mountains of New Hampshire, the Green Mountains of Vermont, the Berkshires in Massachusetts, and the Adirondacks of New York are all part of the Appalachian Mountain range. Read on to discover our favorite snow sports destinations ⛷!
Everyone will enjoy the theaters, museums, and great restaurants of the Northeastern cities and intriguing small towns.
Winter Getaways in Northern New England – Maine, New Hampshire, and Vermont
Burlington, Vermont
Suggested by Emily from Emily Embarks
Perfect for travelers of every age, Burlington, Vermont makes for the ultimate winter getaway from Boston. Known for its laid-back vibe and stunning scenery, Burlington offers a range of winter activities from skiing and snowboarding at the nearby Stowe Mountain Resort, to ice skating on the frozen Lake Champlain.
But there’s more to Burlington than just its outdoor offerings. You can explore Church Street Marketplace for local artisanal products, cozy cafes, live music, and boutique shopping (Saratoga Olive Oil Co. and Lake Champlain Chocolates are fantastic for picking up souvenirs that you can eat!) or even take to the mountains (particularly Mount Mansfield – the highest in Vermont) with snowshoes!
The best part? Burlington has its very own international airport, so you don’t have to make the 3.5-hour, 216-mile drive from Boston!
If you want to make your way through the windy, yet undoubtedly scenic, I-89, you can rent a car right from Boston Logan International Airport. Burlington also makes for a fantastic stopping point on any trip to Canada if you were looking to explore beyond the nation’s borders. But, it is recommended to brush up on your French before making the journey as you’ll find many of the locals in this part of the state are actually from Quebec!
Kennebunkport, Maine
Kennebunkport, Maine is one of my favorite destinations at any time of year! We spent almost half the year in Kennebunk as I was growing up, and though I loved the summer and fall, the winter was magical. The Atlantic beaches are even more beautiful in the winter months and perfect for a (bundled up!) walk or run. There are places to enjoy cross-country skiing and skating. And now you can even enjoy horse-drawn sleigh rides through the snow at Rockin’ Horse Stables!
After your day out, spend the evening in Dock Square, embracing the peace a coating of snow brings to this usually bustling spot. Enjoy some shopping before having dinner at Allison’s Restaurant (my favorite). If you’re in the mood for wine tastings, head to Old Vines Wine Bar in Kennebunk for tapas and tastings. Check their website for live music events.
❤️Named one of New England’s most romantic towns, Kennebunkport is a perfect destination for a romantic winter getaway. In February Kennebunkport celebrates Paint the Town Red. There are ice bars, wine and cheese tastings, candlelight dinners and more for couples to enjoy.
There are so many beautiful options for accommodations in Kennebunkport, but if I were going there this winter, I’d book a room at the Kennebunkport Captain’s Collection.
Kennebunkport is just 90 miles from Boston. If you’re coming from outside of NE, fly into Portland Airport and rent a car for the 22-mile ride to Kennebunkport.
North Conway, New Hampshire
Suggested by Sam at New England Wanderlust
North Conway in the White Mountains region of New Hampshire is often regarded as one of the top ski towns in North America, and is the ultimate destination for couples or families that are looking for lots of opportunities to play in the snow. And since it’s only a 2.5-hour drive from Boston, it’s easy to do in just a weekend.
⛷With over 10 ski resorts within driving distance of North Conway, skiers and snowboarders will have no shortage of slopes to explore. Cranmore Mountain Resort is just a 5-minute drive from the village of North Conway, and is a wonderful mountain for everyone from first-timers to pros.
If you don’t ski, North Conway has you covered, and you’ll have your choice of every outdoor winter activity you can think of including snowmobiling, sleigh rides, ice skating and dog sledding. But one fun activity to consider is spending the afternoon on the Snow Train with Conway Scenic Railway. Leaving from the historic rail station in the heart of the village, this train ride takes you through the mountains up to the Attitash Resort, where you can either hop off for a day of snow tubing or skiing, or head right back down to the village.
After a day of embracing winter weather, enjoy the après ski atmosphere in one of the restaurants. An especially cozy place to check out is Tuckerman Brewing, which has an outdoor beer garden that’s open in the winter. Cozy up by one of their fire pits with a local brew and delicious pizza to end your day.
Portland, Maine
Suggested by Brittany from Travel by Brit
If you’re looking for a chilly yet beautiful winter trip from Boston, look no further than Portland, Maine! Portland is well-known for its rugged rocky coastlines, lobster rolls, and breathtaking lighthouses, but this city has so much more to offer—especially during the winter!
Winter is an ideal time to visit Portland, Maine if you’re traveling on a budget since it’s the off-season, and you’ll find great hotel deals. Plus, Portland is only a 118-mile drive from Boston, so it won’t take long to get here at all. This coastal city is an ideal destination for adventurous couples or solo travelers, especially during the winter. Outside the city, you can go cross-country skiing or snowshoeing or soak up the snowy views at the famous Portland Head Light.
If you’re looking for something to do to stay warm, there are plenty of fun indoor things to do in Portland, Maine, to keep you busy. You can go on a self-guided brewery tour to Allagash Brewing Company, Foundation Brewing Company, and other local craft breweries throughout the city. You can also explore the boutique shops and local eateries in Old Port or grab a bite to eat at Duckfat or Eventide Oyster Co.—two of the most popular restaurants in Portland. Or you can even go on a guided food tour to sample all the best bites in the city!
Portsmouth, New Hampshire
Suggested by Christine from Live Love Run Travel
Portsmouth, New Hampshire, is one of the best winter getaways from Boston. At just an hour away, you can make take a day trip to Portsmouth from Boston or even a longer weekend getaway to explore more of the city.
Portsmouth is a great place for couples or adults in the winter. If the weather is nice, take a stroll around Market Square to enjoy the shops and restaurants in the area. Eat a meal at the nearby River House restaurant with views overlooking the water and a heated and enclosed patio.
You can also take a trip out to Four Tree Island for a great view of Memorial Bridge and drive through the beautiful islands of New Castle to admire the New England architecture of the stunning homes in the area.
If you like museums, check out the USS Albacore Museum which is open daily. You can take a tour through the former research submarine to learn its history.
If you are feeling a little more adventurous, take a drive out to Wallis Sands Beach where you can watch the waves crash and relax in the salty air even if it’s much too cold for a swim.
The Hotel Portsmouth is a great hotel if you plan to stay overnight. Built in 1881 as a private home, it offers spacious rooms and a delicious breakfast to start your day. With several common areas, you’ll have room to relax and be in walking distance of Market Square.
Stowe, Vermont
Suggested by Heather Kasvinsky from This Noshtalgic Life
If you’re looking for a scenic winter getaway, Stowe, Vermont should be at the top of your list. As only a 3-hour drive from Boston, Stowe is an easy destination to travel to for families and couples alike!
⛷From its world-famous skiing and snowboarding opportunities to its charming small-town atmosphere, Stowe has something for everyone. As the town often experiences temperatures well below freezing, the winter months may be one of its most beautiful periods, followed closed behind by the fall season.
Be sure to head to Laughing Moon Chocolates for a sweet treat. This locally owned and operated shop is known for its delicious handmade chocolates. From classic flavors like milk and dark chocolate to more unique options like lavender and honey, you will leave smiling with a bagful of gifts for friends and family.
A visit to Trapp Family Lodge is a must if even just to see the beauty of this Austrian-inspired hotel established by the famous von Trapp family. The cross-country ski center at Trapp’s is world-class and skiing the trails is a must for any serious nordic adventurer!
Even if skiing or snowboarding isn’t your thing, Stowe is definitely still worth a visit. Plus, it has one of the best aprés-ski scenes on the east coast that you can enjoy.
There are also plenty of other activities to enjoy in town, including shopping, wine and cheese tasting, fine dining, horse-drawn carriage rides, and exploring the natural beauty of the area. In addition, with so many cozy accommodation options, you’ll be glad you made the trip!
Winter Getaways in Massachusetts and Southern New England
The Berkshire Mountains in western Massachusetts are lovely in all seasons, but are especially good for snow sports in the winter. There are many charming small towns to visit but our favorites for winter getaways in Massachusetts are Stockbridge and North Adams.
Stockbridge, Massachusetts
Stockbridge is a classic New England Town; the kind of town you would see in Norman Rockwell’s paintings. And that’s no coincidence as Stockbridge is where the artist lived and where today you’ll find the Norman Rockwell Museum.
This museum alone is well worth the trip, but there’s many other attractions in the Stockbridge area. There are wonderful shops and galleries to explore on Main Street. There’s cross country skiing and ice fishing on the Stockbridge Bowl. And for the skiers there are the nearby mountains.
Stockbridge makes a good home base for exploring the Berkshires. Book a room at the historic Red Lion Inn, visit the museums, and then head out to enjoy the surrounding area.
- Our favorite mountain for beginner skiers and snowboarders is Butternut Basin in Great Barrington, just 15 minutes south of Stockbridge. Ski Butternut features gentle, well-groomed slopes perfect for young families. Snowboarders will enjoy the unique terrain park in the resort.
- 15 minutes north of Stockbridge is the beautiful town of Lenox, Massachusetts. Take a scenic drive to Lenox to see the famed mansions and historic homes. Enjoy lunch at one of the restaurants specializing in healthy, locally grown food. Note: Lenox is home to Canyon Ranch Wellness Spa. Look into a stay there if you’re interested.
Stockbridge is 131 miles from Boston and 145 miles from New York City.
North Adams, Massachusetts
Suggested by Emily Pollakowski, New York family photographer
A bit further north from Stockbridge is the charming town of North Adams, Massachusetts. Tucked into the northwest corner of Massachusetts, North Adams makes a great base for exploring the Berkshires as well as the mountains of southern Vermont.
Art lovers come to North Adams to visit the Massachusetts Museum of Contemporary Art (Mass MoCA), one of the largest centers of visual and performing arts in the U.S. The museum complex was once an old mill, the Arnold Print Works factory buildings. Mass MoCA has repurposed this complex into a spectacular light-filled three floors of contemporary art.
☃️This is a wonderful museum for everyone, young and old, and the perfect place to let little ones burn off some energy on a rainy day. The expansive spaces allow kids to run and explore, the interactive music and art rooms are a delight for kids who want to be hands-on, and the art that surrounds you — from the paintings and sculptures, to the walls themselves — opens a door for children to talk about art and find creative ways to express themselves.
For the outdoorsy travelers, there are options all around North Adams. Jiminy Peak is a half hour drive, with great trails for skiing and snowboarding. Best of all, Jiminy Peak now gets 100% of its electrical power from renewable sources! The Appalachian Trail also runs through North Adams, as do many other hiking and biking trails and parks.
Home to the Massachusetts College of Liberal Arts and one town over from Williamstown, home to Williams College, North Adams has a flourishing dining and entertainment scene for college students and parents alike. Just beyond the front door of Mass MoCA, you’ll find Bright Ideas Brewing, a modern craft brewery with indoor and outdoor seating. A little further downtown, you’ll find PUBLICeat+drink, a lively spot for inspired American comfort food, craft beer & cocktails. Just make sure you get there early — this one fills up quickly and people tend to linger. And with Mac + Cheese served with pancetta, smoked gouda and roasted tomato, who wouldn’t linger?
❤️North Adams is a lovely spot for a winter getaway from Boston or from NYC! Stay in one of the cozy rooms at the Porches Inn at Mass MoCA. The Inn’s tagline – Where Art Meets Whimsy – is reflected in each distinctive row house. Plus, there’s a heated outdoor pool, hot tub and sauna to help you unwind after a long day of skiing or exploring. If you’re lucky, you’ll schedule your stay while there’s a performance at Studio 9, an intimate state of the art recording studio and performance venue located on the Inn’s property. Whether enjoying a romantic getaway or a family ski weekend, this cozy boutique inn is a great choice in North Adams.
Essex, Connecticut
Nestled on the Connecticut River just a few miles for Long Island Sound is the historic town of Essex Connecticut. This is a lovely place to stay to enjoy Connecticut in the winter months.
The Connecticut River Museum in Essex features a family-friendly train show from Novermber through February, as well as other exhibits on the history of the Connecticut River.
☃️At Christmas time the famed Essex Steam Train is transformed to the North Pole Express. Kids will delight in this 90-minute adventure. Tickets sell out early so plan ahead! Not visiting with kids? This year Essex Station celebrates New Year’s Eve with a Roaring 20s Murder Mystery Gala!
Venturing away from Essex you can enjoy a walk on Old Saybrook’s waterfront, a visit to Mystic Aquarium or head to the Mohegan Sun Casino and Resort, one of Southern New England’s most popular casinos.
Stay at the historic Griswold Inn. This hotel opened in 1776 and has been continuously operating since! The inn has kept up with the times and is a lovely spot for a romantic getaway. Enjoy Griswold’s Wine Bar and Bistro, or venture out for dinner to another historic spot, the Copper Beach Inn.
Hyannis, Massachusetts
Cape Cod is known for summer and autumn attractions, but many don’t realize how lovely it is in the winter. The crowds of summer are gone and the Cape quiets. This is the perfect time to enjoy the beauty of the empty seashore, snow-covered salt marshes, and the coziness of a Cape Cod town.
Just 70 miles from Boston is the town of Hyannis. Unlike some of the towns in the outer cape, Hyannis is a vibrant year-round town. Stroll down Main Street to enjoy shopping and some great little restaurants. This is where the John F. Kennedy Hyannis Museum is located, so stop in for a visit to learn more about the 35th President and the legacy of the Kennedy family in Hyannis. (open Thursday – Sunday)
☃️ If you’re traveling with the kids, book a room at the Cape Codder in Hyannis. Its indoor pool and water park is an oasis on a wintry day. Take a tour of the Cape Cod Potato Chip factory, and visit the oldest aquarium in the U.S., the Woods Hole Aquarium. If you visit while the weather is mild, you can enjoy walking or cycling the Cape Cod Rail Trail.
❤️ If you’re looking for a quieter more romantic winter getaway, drive a bit beyond Hyannis to the Chatham Bars Inn. This historic New England Inn overlooks Chatham Harbor and the Atlantic Ocean. Consider booking the spa retreat package which includes 2 nights’ stay and $600* toward spa services. A perfect romantic winter getaway!
Hyannis is just over an hour drive from Boston but if you don’t want to drive, book the Plymouth and Brockton bus from Boston.
Fitchburg, Massachusetts
☃️We’re including this small town in northern Worcester county as a family favorite destination to escape the cold and snow. Fitchburg is where you’ll find Great Wolf Lodge, legendary for its indoor waterpark. But that’s not all the lodge has to offer. Your family can enjoy Magiquest, an interactive adventure game, and lots of other activities and crafts. A weekend at Great Wolf Lodge will be fun for all the family.
But don’t spend all your time at the lodge. Venture out to explore the Fitchburg Art Museum or head to nearby Wachusett Mountain for skiing and snowboarding. End the day at the Wachusett Brewing Company, a craft brewery in Westminster, Massachusetts.
Fitchburg is less than 50 miles from Boston. This would make a good stop on the way from Logan Airport to the northern ski resorts.
Newport, Rhode Island
Suggested by Amanda from My Vintage Map
Newport, Rhode Island is a perfect winter destination from Boston and is especially fun for couples and families with older children. This charming coastal town is only 72 miles south of Boston, or roughly 1.5 hours by car.
Tourists flock to Newport in the spring, summer, and fall, which means it’s a lot busier during those seasons. If you visit during the winter, you can still enjoy the same popular attractions while avoiding the crowds.
The best thing to do in Newport is visit one of the historic mansions—The Breakers is the most famous. If you grab one of the audio headsets near the entrance, you’ll learn all about the Vanderbilt family and the way they lived during the Gilded Age.
Close to the mansion is the Cliff Walk, a 3.5-mile paved trail that runs along the Atlantic Ocean and offers stunning views the entire way. If you bundle up well, you can still enjoy this scenic walk in the winter!
During your visit, it’s also worth touring downtown Newport and browsing the galleries, boutiques, and souvenir shops. The White Horse Tavern is the oldest operating restaurant in the United States and would make for a memorable meal in town.
Hotel Viking is on the list of Historic Hotels of America and is an easy walk from the town center. Another perk of visiting Newport in the winter is this hotel will be significantly cheaper than during other times of the year.
Boston, Massachusetts
For many of us suburbanites the best winter getaways in Massachusetts are in Boston. It’s a short trip into the city but a world away from our day to day. There is shopping, and theaters, and fabulous restaurants in the North End to try. If we’re feeling cultured, we spend the day at one of Boston’s outstanding museums, and enjoy a concert at Symphony Hall in the evening. But if we’d prefer a sporty weekend, we tour Boston’s historic Fenway Park and skate on the Frog Pond on Boston Common.
There’s something for everyone in Boston. In the winter the Boston Celtics and Bruins attract large crowds. Check well ahead if you want tickets, but if they’re sold out, watch the game at Boston’s Cheers or another of Boston’s neighborhood pubs.
❤️For a romantic weekend getaway we’d recommend booking the Fireplace Experience package at the Lenox Hotel. How often can you stay at a legendary hotel with a wood-burning fireplace in your room?
Other fun things to do on a winter trip to Boston: Explore picturesque Beacon Hill, have lunch at the Parker House (home of the Boston creme pie), enjoy afternoon tea at the Boston Public Library, or experience First Night.
Winter Getaway Destinations in New York
New York City, New York
Suggested by Kelly of Travel New York Now
Looking for one of the best winter getaways from Boston? If so then you can’t beat NYC.
Not only is it a short, 4-hour train ride from Penn Station to Boston but NYC is overflowing with incredible winter activities for you to enjoy.
Start your trip off by heading to Rolf’s German restaurant. While you’re here you can admire the stunning Christmas bulbs and decor before grabbing a holiday-inspired cocktail from the bar.
Next, grab some chocolate babka from the Breads Bakery kiosk in Bryant Park before going ice skating on the rink here. You can also try your hand at curling and shop among the park’s incredible holiday-inspired vendors before heading to Brookfield Plaza to admire the colorful luminaries dangling from the ceiling of the palm tree-filled atrium.
☃️You can also go for an ice skate outside while overlooking the river before checking out the giant Christmas tree at Rockefeller Center which is one of the best things to do in NYC with kids.
And if you’re not a fan of the cold you can always warm up while watching a Broadway show or while admiring the Butterfly Conservatory at the American Natural History Museum.
Whatever you do though just don’t leave the city without grabbing a delicious cup of steaming hot chocolate from Mariebelle.
Because regardless of whether you’re traveling to NY alone, as part of a couple, or as a family, it is the perfect destination for you.
Lake Placid, New York
Lake Placid holds a special place in winter sports history. This small town in the Adirondack Mountains has hosted the Winter Olympics twice, in 1932 and again in 1980. Only nine other cities have hosted more than once and most are big cities – London, Paris, Tokyo, Los Angeles, and Beijing. The fact that a small town was chosen for two Olympics gives you an idea of the suitability of the area for winter sports.
The legacy continues in Lake Placid with world class athletes still training on the speed skating oval, the ski jumping complex, and Whiteface Mountain. There’s a fascinating Olympic museum well worth a visit.
Once inspired head out to enjoy winter sports yourself. There are two cross-country ski centers, ice skating on Mirror Lake and even a bobsled experience for visitors to try.
⛷ But the majority of winter sports enthusiasts come for Whiteface Mountain. Skiers and snowboarders can find some of the best skiing on the east coast. Whiteface Mountain boasts the greatest vertical drop east of the Rocky Mountains.
For a full resort experience book a room at the Mirror Lake Inn & Spa. Book ahead for a romantic getaway. You can ski in the morning and relax afterwards with a couples massage at the full-service spa.
Lake Placid is about 5 hours from Boston or NYC by car, but don’t let that deter you. You can travel to Lake Placid by Amtrak train or by bus. And if you’re coming from outside the Northeast, you can fly to a closer major airport and rent a car, or fly directly to the Adirondack Regional Airport.
I’m looking forward to several weekends away this winter season. We find enjoying outdoor activities and exploring our region makes the winter go quickly. Hope you found some winter getaways in the Northeast that appeal to you. See you there!
*price at time of publication.
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Amy, a writer and researcher on responsible bucket list travel, is your reliable source for insightful travel advice. With a career background in libraries, and a degree in biology, Amy's approach to travel is rooted in meticulous planning and a commitment to eco-conscious and accessible adventures.
Amy’s dedication to sustainable travel practices, including efficient packing techniques, ensures that every adventure leaves a positive impact on both the environment and the traveler's well-being. Trust Amy to guide you towards meaningful and eco-friendly travel, making the most of your retirement years.
A lifelong New England resident, Amy is also the source for insider tips on travel in the Northeastern U.S.
Oh I so wish I could be there in a heart beat, every one of these looks so appealing. I always think of New York at this time of the year as my ultimate winter destination. You have shown me so much more. I have an Aunt in Connecticut I must visit in Winter!
I have heard a lot about Rhode island. It sounds worth every penny. Thank you for sharing.
Out of all these places, I’ve only visited NYC. I would love to explore these cute, charming New England destinations!
I haven’t visited any of these during the winter, but they so iconic and perfect!
With this dreary early winter weather I’ve been kind of dreading it. However, to see all these fun things to do in places not too far from me makes me more excited to get out and enjoy. I especially want to visit New Hampshire this winter.
What a long list to choose from! Even hard to decide what could be my first choice. Maybe Stowe, Vermont. I am so tempted with wintery picture. Thanks for sharing!
Great list! I grew up on the CT/MA border and I still have never been to most of these places (winter was always “hide from the snow inside” time), but I’d love to explore the area more as an adult. I do remember doing the essex train as a kid and thinking it was awesome.