Home ยป Top 10 New England Winter Getaways & Activities For Each

Top 10 New England Winter Getaways & Activities For Each

Do you love charming New England towns & streets, festive cafes decorated with lights, and beautiful snowshoe or ski trails?!

If you’re looking for an adventurous getaway, a “#1 ski town in the US“, or just want to stroll quaint New England streets and shops – you’ll find it all on this New England winter getaway list!

I put my decades of living and exploring in New England into this post so you can find the perfect escape and best New England getaway this winter!

And don’t just take my word for it! These towns have repeatedly shown up in lists of favorites from Travel + Leisure, Smithsonian Magazine, and Martha Stewart of which I note for each one.

In addition to a list of the best New England winter towns, you’ll also find a list of indoor and outdoor activities for each location. Sample activities include:

  • Festive woods walks decorated with lights โœจ
  • Ice Castles ๐Ÿฐ๐ŸงŠ
  • Santa’s Village ๐ŸŽ„
  • Magical train rides to the top of the mountain in the Northeast! ๐Ÿš‚
  • A village that has 13 ski areas within a 30-minute drive โ›ท

๐Ÿ—บ Location: Included in this post are magical New England towns way up north and southern gems in case you want to keep your drive short or not experience as much snow or cold.

So pack your favorite wool sweater, a good book, and maybe your pup that will be trodding the trails with you and cuddling by the fire!

๐Ÿ†Overall Awards- A Quick Listโ„๏ธ


๐Ÿ…Best for skiing: North Conway, NH

๐Ÿ…Best for a relaxing winter getaway: Stockbridge, MA

๐Ÿ…Best for a little of everything: (ski, shop, hike, snowshoe): Woodstock, VT
๐Ÿ…Best outdoors & artsy destination: Williamstown, MA
main street great barrington decorated for christmas time
Love the quaint downtown on Great Barrington (town in the Berkshires) during the holidays! ๐ŸŽ„

Known for its picturesque towns and villages, right out of a Thomas Kinkade puzzle ๐Ÿ˜ there are lots of New England towns to choose from for a quintessential relaxing winter getaway.

The following locations are great options to enjoy the simple pleasures of a Northeast town in winter; sipping hot cocoa by a roaring fire, admiring or snowshoeing through snowy fields, or strolling through quaint ski towns. Be as active or relaxed as you want to be!

The Best Most Charming Winter Destinations in New England

1. The Southern Berkshires: Stockbridge, Great Barrington, & Lenox, Massachusetts

Why it’s on the list:While eastern Massachusetts serves as the economic engine of the state, those in search of captivating rural beauty should make their way to the Berkshires on the Western edge.” ~forbes.com

Forbes knows, and I know, too, after living and exploring here for four years.

With more than 100 world-class cultural attractions, superior outdoor recreation (hiking, skiing, snowboarding), and a famous farm-to-table food scene, no southern New England winter getaway that’s better than the Berkshires.

This destination in southern New England is chock full of festive winter activities. (So many that I made a whole separate post detailing 33 festive and fun winter activities in the Berkshires!)

With so much to do packed into tiny towns that are just minutes from each other so you can explore Great Barrington, Stockbridge, and Lenox, too! (Stockbridge is in the middle of GB and Lenox.)

๐ŸŽ„ Indoor Winter Activites ๐Ÿ–ผ๐ŸŽ„๐ŸŽฟ Outdoor Winter Activities ๐Ÿฅพ
Historic Holiday Mansions Tour (December only) Magical NightWood at Edith Wharton’s historic home, The Mount
Visit Berkshire Museum (if during December see their Festival of Trees!) WinterLights at historic mansion Naumkeag (end of Nov – Jan)
Take a class, weekend course, or retreat at Kripalu Yoga Center, the largest retreat center in North America! See my best hikes in the Berkshires list here!
Visit a world-class spa at Canyon Ranch or Miraval Resort and Spa (both in Lenox)Hike the popular Monument Mountain in Great Barrington, 2.4 mi (Moderate)
World-renowned Norman Rockwell Museum in StockbridgeBash Bish Falls the tallest waterfall in MA
Visit the can’t-miss Chocolate Springs Cafe in Lenox (named a top 10 chocolate maker in the US!)Ski or snowboard at Ski Butternut in Great Barrington or nearby Catamount Ski

2. Manchester, Vermont

Why it’s on the list: Can you say cute and quaint?! A beautiful southern VT location that offers skiing, amazing hikes and trails, lots of shopping and streets for strolling, and historic sites to visit.

Experience the romance, beauty, and quaintness of Manchester! Manchester is a town in southern Vermont that’s packed with top-rated places to eat, shop, explore, and unwind.

I love that this town is only 2.5 hours away from me in central Connecticut but you still get that quintessential Vermont feel without a 4-hour drive.

Here’s a post I wrote about a pet-friendly Airbnb/Vrbo stay I love that’s right near Manchester! With the most amazing mountain views. ๐Ÿ˜ฑโ›ฐ

Manchester, Vermont is the ideal location to take in the magic of the snowy winter season and especially during the holidays if you can go in December. The Shiresโ€™ Holiday Inn Tours, a favorite of many residents and tourists, are self-guided tours through some of the best lodging establishments in Vermont all decked out in their holiday best. ๐ŸŽ„๐ŸŽ„

And if you’re feeling in the mood to adventure, I loved the hike up to Lye Brook Falls hiding right in the center of Manchester.

Top Winter Activities in Manchester, Vermont:

๐ŸŽ„ Indoor Winter Activites ๐Ÿ–ผ๐ŸŽ„๐ŸŽฟ Outdoor Winter Activities ๐Ÿฅพ
Museum of the Creative ProcessLye Brook Falls Trail, 4.5 miles (Moderate)
Manchester Music FestivalProspect Rock Trail, 3.1 miles (Moderate)
The American Museum of Fly FishingEquinox Pond Trail, 2.5 miles (Easy)
Tour Hildene, the Lincoln Family HomeEquinox Mountain & Lookout Rock, 6.3 miles (Hard)
Green Mountain Academy
for Lifelong Learning
(take a class!)
Ski at Bromley Mountain (15 min away)
Ski/ride at Stratton Mountain Resort (27 min away)
Click here for full list of Skiing and Riding Resorts

3. Woodstock, Vermont

Why it’s on the list: “When you visit Woodstock, youโ€™ll uncover a place thatโ€™s brimming with rural heritage and tranquil beauty that flows through a small-town community. Local farmers, artists, craftspeople, and purveyors capture the spirit of Woodstockโ€™s village, inspiring visitors to discover the creative treasures that lay waiting.” ~woodstockvt.com

A classic Vermont town that must be on our list! Located a bit further north than Manchester and east of Killington, Woodstock is home to the only national park in Vermont and three historic covered bridges.

This town feels untouched by modern civilization. Aside from the small downtown with the cutest shops, restaurants, galleries, and cafes to walk around – you won’t find (or at least I didn’t) a big box or chain store here.

And if you’re celebrating something special or want the ultimate Woodstock experience, check out the Woodstock Inn & Resort. It has its own cross-country/nordic ski center with 27 miles of groomed trails for cross-country skiing and snowshoeing. (Availability & prices here). (Be sure to pop in and see it even if you don’t stay there! ๐Ÿ™‚ They have a full spa as well.)

๐ŸŽ„ Indoor Winter Activites ๐Ÿ–ผ๐ŸŽ„๐ŸŽฟ Outdoor Winter Activities ๐Ÿฅพ
World-renowned Spa at Woodstock Inn & ResortA Forest of Lights, Experience the magic of a Forest Canopy Walk as you take in the lights of the season. Campfire, hot chocolate, & snacks!
American Precision Museum or stroll around the cutest downtown shopping areaAnnual Wassail Weekend; a celebration of the sights,
sounds, and spirit of winter
(beginning of December)
The Vermont Institute of Natural ScienceMultiple scenic hikes nearby (click here for my post
on 6 different hikes in/near Woodstock!)
Marsh-Billings-Rockefeller National Historical Park ToursWalk, hike, snowshoe, or cross-country ski
at Marsh-Billings-Rockefeller National Historical Park
All nordic skiing & snow shoeing locations here
Ice skate at Union ArenaSki or snowboard at Saskadena Six Ski Area
or at Killington Ski Resort

4. Litchfield, Connecticut

Why it’s on the list: Designated as a National Historic Landmark District in 1968, Litchfield is a well-preserved example of a typical late 18th-century New England village. There’s so much to do packed into this quaint New England town I wrote a post about 31 fun things to do in Litchfield!

Litchfield was named a top 20 getaway in New England by Travel + Leisure Magazine: “A small town that more than carries its weight on the history, charm, and scenic beauty fronts.

This picture-book spot in rural western Connecticut (birthplace of Revolutionary leader Ethan Allen and abolitionist Harriet Beecher Stowe) has an oak-shaded town green and hundreds of historic buildings.” ~travelandleisure.com

I lived here for several years. It’s truly a quintessential New England town that becomes extra cozy and charming in winter!

Between the town green established in 1720, the meetinghouse from 1829 and the shops and highly rated restaurants casting glows from their windows as the sunsets – how could you not want to see it all covered in snow! Or at least see it with holiday decorations and twinkling lights.

Be sure to walk down North Street, across from the green, with its mega historic homes (homes of Revolutionary War Colonels). It was my favorite place to walk when I lived here, wondering about the lives and decor within one of these old, historic mansions. The whole town is very walkable!

If planning a trip to Litchfield, here’s a link to a post I wrote about the best inns to stay in Litchfield County!

๐ŸŽ„ Indoor Winter Activites ๐Ÿ–ผ๐ŸŽ„๐ŸŽฟ Outdoor Winter Activities ๐Ÿฅพ
Visit the Litchfield Historical Society, one of the 7 art galleries, or the Litchfield DistilleryWalk, snowshoe, or cross-country ski at White Memorial Conservation Center; 4,000 acres of preserves, much of it nestled against Bantam Lake, with 40 miles of trails
Visit the nation’s first law school at Tapping Reeve House and Litchfield Law SchoolHike up to Prospect Mountain, 2.3 miles (Moderate)
Hike up to Mount Tom Tower via a 1.3-mile trail (Moderate)
Hike to Apple Hill Observation Deck, 1 mile (Easy)
Pamper yourself at The Spa at Litchfield HillsSki or snowboard at Mohawk Mountain
Catch a show at the historic (non-profit film and arts center) Bantam CinemaWalk the trails in one of CT’s prettiest state parks; Topsmead State Forest

5. Kent, Connecticut

Why it’s on the list: “A superb balance of old and new, quaint and chic, old-fashioned and avante garde. Owner-operated shops offer stylish and eclectic goods from home and abroad. Restaurants that serve inventive dishes from local ingredients.

Galleries feature quality contemporary and classic art. From the rolling river with its historic covered bridge to Kent Falls to the Appalachian Trail and hills made for biking, Kent offers varied of outdoor activities.” ~ctvisit.com

Another Connecticut gem to visit this winter! I would choose Kent if you’d like an active trip with lots of hiking, snowshoeing, or skiing.

If you’d like to plan a trip to Kent, check out my post about the best inns to stay in Litchfield County or my post about 24 fun activities in Kent!

๐ŸŽ„ Indoor Winter Activites ๐Ÿ–ผ๐ŸŽ„๐ŸŽฟ Outdoor Winter Activities ๐Ÿฅพ
Visit Kenise Barnes Fine Art GalleryHike part of the Appalachian Trail (7 hikes to choose from here)
Visit Kent Falls Brewing CoShort walk to Kent Falls at Kent Falls State Park, CT’s tallest waterfall!
Kent Coffee & ChocolateHike up to Caleb’s Peak via Fuller Pond, 4.4 mi (Moderate)
 Gallery at the Kent Art Association or Eric Sloane Museum and Kent FurnaceHike one of the trails at the beautiful Macedonia Brook State Park, (3 to choose from here)
Connecticut Antique Machinery Association MuseumSki Mohawk Mountain

6. Lincoln, New Hampshire

Nestled in the heart of the White Mountains, Lincoln, New Hampshire is a quaint town that offers an adventurous and active winter getaway.

If you are looking for either a serious ski destination or one where you can work up a sweat cross-country skiing or snowshoeing, then Lincoln is the winter getaway for you.

Or maybe you want to sit all aboard on the first-in-the-world mountain-climbing cog railway! The Cog has been making its dramatic three-hour round trip to the summit of the highest peak in the Northeast (6288โ€™) since 1869. Up to Mount Washington, that is!

๐ŸŽ„ Indoor Winter Activites ๐Ÿ–ผ๐ŸŽ„๐ŸŽฟ Outdoor Winter Activities ๐Ÿฅพ
Visit Santa’s VillageExplore the Ice Castles
Visit Loon Mountain ResortHike/snowshoe Franconia Notch State Park
Living Shores AquariumSki, tubing, or “Snow-Go’ at Loon Mountain
Visit, stay, or eat at the historic and famous Omni Mount Washington Resort (it’s worth a walk-through!)Franconia Village Cross Country Ski Center
Take New Hampshire’s longest scenic gondola ride to the summit of Loon PeakWinter train ride up the tallest mountain in the Northeast on The Cog

For a luxurious stay, consider the Loon Mountain RiverWalk, which features a spa, winery tasting room, and an on-site restaurant.

7. Jackson and North Conway, New Hampshire

North Conway was named the #1 Ski Town in the United States with thirteen ski areas located within a thirty-minute drive of the village. And also one of the Top 10 Best Small Towns in America for Adventure by readers of USA Today! It must be included on any top New England winter destinations list.

It is also a town named a top 20 getaway in New England by Travel + Leisure Magazine:

“These sister towns in New Hampshireโ€™s pretty Mount Washington Valley make a popular getaway, thanks to their waterfall hikes, scenic drives, small-town shopping (Schartner Farms has a drive-up, honor-system jam stand โ€” how cute is that?), and big-box outlets. 

On the highway between the two towns is Sunrise Shack, an old-school drive-in-restaurant turned roadside staple for truly enormous breakfasts.” ~travelandleisure.com

Running list of White Mountain holiday activities here.

๐ŸŽ„ Indoor Winter Activites ๐Ÿ–ผ๐ŸŽ„๐ŸŽฟ Outdoor Winter Activities ๐Ÿฅพ
Shop tax-free at the Settler’s Green Outlet Village; local hand-craft, antique and gift shops!All aboard the Conway Scenic Railroad for Santaโ€™s Holiday Express or the Snow Train
Drive the famous Kancamagus Scenic Highway with its super scenic viewsDiana’s Baths Waterfalls, 1.3 miles (Easy)
Visit Mount Washington Observatory Weather Discovery CenterVisit Echo Lake State Park, hike up to Cathedral Ledge, all trails listed here
Visit one of the 10+ art galleries listed hereTake a horse-drawn sleigh ride!
Live music, dining, and more at Cranmoore ResortTubing, skiing, skating, snowboarding, ziplines, and snowmobiles. All winter activities listed here

8. Newport, Rhode Island

Another New England town that made Travel + Leisure’s best weekend getaways in New England list!

Newport, Rhode Island, is a historic coastal town that boasts magnificent Gilded Age mansions and a stunning waterfront.

“Think cobblestone streets lined with the glow of white lights, the glitter and gold of Gilded Age mansions bedecked with dozens of Christmas trees and thousands of poinsettias, and warm, quaint shops with candlelit windows. Truth be told, enchanting doesn’t quite begin to explain it.” discovernewport.org

During the winter season, the town takes on a magical atmosphere, with the mansions and their halls decked out in lights! Winter is a great time to take advantage of everything Newport has to offer with way fewer crowds.

๐ŸŽ„ Indoor Winter Activites ๐Ÿ–ผ๐ŸŽ„๐ŸŽฟ Outdoor Winter Activities ๐Ÿฅพ
Holidays at the Newport Mansions (til Jan 1st!)Leisurely stroll through Norman Bird Sanctuary; a private nonprofit wildlife refuge and environmental education center
Visit The Bodhi Spa; New England’s Premier Hydrotherapy SpaSee scenic views (without a climb!) at Sachuest Point National Wildlife Refuge
Tour the Newport Mansions or historic sites (even after the Xmas lights)East Bay Bike Path; weaves through coves, marshes, parks and bridges
Museums & art galleries listed hereThe famous 3.5 mile Newport Cliff Walk
Check out the unique shops along cobblestone Thames StreetOther hikes or walks listed here!

9. Williamstown, Massachusetts

Called “One of the loveliest communities in New England” by the New York Times, Williamstown is a college town in the northern Berkshires.

Williamstown deserves a spot on this list separate from the southern Berkshire towns in number 1. An hour further north, it has its a plethora of indoor and outdoor activities to fill up a winter weekend and more.

๐ŸŽ„ Indoor Winter Activites ๐Ÿ–ผ๐ŸŽ„๐ŸŽฟ Outdoor Winter Activities ๐Ÿฅพ
Visit Mass MoCA (museum of contemporary art)Hike Mount Greylock, the tallest mountain in Massachusetts!
Visit The Clark Art InstituteProject Snowshoe (snowshoe outside The Clark museum’s 140 serene acres!)
Visit Bright Ideas BrewingHike the Cascades Trail to a beautiful waterfall, 2.2 mi (Easy)
Images Cinema; an independent 501c3 movie theaterCross-country ski or snowshoe at Stump Sprouts Cross Country Ski Center
Catch a show at Berkshire Theater GroupSki Berkshire East

10. Portland and Freeport, Maine

MarthaStewart.com named this area one of โ€œThe Most Charming Small Towns to Visit During the Christmas Seasonโ€. She says, โ€œThereโ€™s simply no better place to do your Christmas shopping than in Freeport, Maine.โ€

Food lovers will delight in a winter getaway to Portland, Maine, where you can indulge in the townโ€™s thriving culinary scene. From lighthouse exploration to ice skating and cross-country skiing, thereโ€™s no shortage of adventures to be had in this charming coastal city.

Portland is also home to a vibrant arts and culture scene, with numerous galleries, museums, and theaters to explore.

๐ŸŽ„ Indoor Winter Activites ๐Ÿ–ผ๐ŸŽ„๐ŸŽฟ Outdoor Winter Activities ๐Ÿฅพ
All aboard! Polar Express Train RideAttend the Sparkle Celebration; Maineโ€™s most popular holiday celebration (first half of December)
Portland Museum of ArtSki at Sunday River
Visit one of Portland’s numerous historic landmarks and PortsMoose watching tours or guided hikes with Northeast Whitewater
Visit Southworth PlanetariumBack Cove; Portlandโ€™s very own outdoor exercise rink
All other indoor activities listed hereBaxter Woods; Portland’s largest forest

I hope you enjoyed this list of the best winter winter getaways in New England!

There’s truly a winter getaway for everyone here; charming towns to romantic escapes, thrilling winter sports or adventurous winter vacations.

The in and outdoor activities will leave you with not much time to sit and sip your hot cocoa! But you can choose to do more or less depending on how active you want to be on your winter vacation.

Frequently Asked Questions

What to pack for a New England winter getaway?

You’ll want to pack the essentials so you can stay warm and comfortable and not dread walking around outside or leaving your cozy inn!

I have a whole post detailing what to wear when walking or hiking in cold weather. Use that to pack the essentials if you’re planning on being outside a lot on your trip.

Here’s a list of a few essentials:

  • Waterproof boots (especially if you plan to snowshoe or hike!)

  • Fleece or wool hat

  • Winter jacket
  • Fleece lined mittens

  • Sunscreen (the winter sun can be strong especially if reflecting on the snow!)

What is the best thing about winter in New England?

Growing up and living here all of my life, I think the best thing about New England winter is its charm and wide range of activities! From world-class mountains for skiing in Vermont and New Hampshire to visiting the Newport Mansions.

Just strolling and admiring the quaint downtown villages decorated in lights is one of my favorite things about winter vacations in New England.

I also love warming up by snowshoeing or cross-country skiing and then enjoying a hot meal, latte, or hot chocolate at one of the amazing restaurants in the area!

Where can New Yorkers vacation in the winter?

Residents of NYC may prefer to head to southern areas like Litchfield County in CT or southern Vermont (Manchester).

Where can I find the best adventure-filled winter getaways in New England?

As mentioned in this list the best winter getaways in New England are primarily in:

  • the Berkshires in Massachusetts (Stockbridge and Williamstown)
  • Litchfield County in Connecticut (Kent and Litchfield)
  • Woodstock, Vermont
  • Portland or Freeport, Maine
  • White Mountain towns like Lincoln or North Conway, New Hampshire
  • Newport, Rhode Island

What are some romantic winter escapes in New England?

I think the most romantic winter spots in New England would be Woodstock, Vermont, and Litchfield, Connecticut! Get a room at an inn with a fireplace and you’ll be all set. ๐Ÿ˜

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