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?!
Whether you’re looking for an adventurous getaway, a “#1 ski town in the US“, or a quaint New England town to stroll – 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 this winter. 🌟 You’ll find an indoor and outdoor activities list 📝 for each location – all the work is done for you! 😍❄️
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.
🌟Activities for each destination include….
- Festive woods walks with lights ✨
- Ice Castles 🏰🧊
- Santa’s Village 🎄
- Magical train rides 🚂
- A village with 13 ski areas ⛷
So pack your favorite wool sweater, a good book, and maybe your pup that will be walking the trails with you and cuddling by the fire! 🧤
Enjoy the simple pleasures of a Northeast town in winter; sipping hot cocoa by a roaring fire, snowshoeing through snowy fields, or strolling through quaint ski towns. (📸 dog-friendly VRBO in Manchester, Vermont w/mountain views!)
The Most Charming Winter Destinations in New England
1. Southern Berkshires, Massachusetts: Stockbridge, Great Barrington, & Lenox
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
After living and exploring here for years, I’ve learned first hand that this destination in southern New England is chock full of festive winter activities. Hence my post 👉 33 festive and fun winter activities in the Berkshires
These tiny towns are just minutes from each other so you can explore Great Barrington, Stockbridge, and Lenox, too, no matter where you choose to stay in.
Indoor Winter Activities 🖼🎄
- Historic Holiday Mansions Tour
- Berkshire Museum (Festival of Trees!) or Norman Rockwell Museum
- Kripalu Yoga Center, Canyon Ranch Spa, or Miraval Resort and Spa
- Chocolate Springs Cafe (named top 10 chocolate maker in US!)
🎿 Outdoor Winter Activities 🥾
- Magical NightWood The Mount
- WinterLights at historic mansion Naumkeag (end of Nov – Jan)
- Choose a hike in the Berkshires!
- Ski or snowboard at Ski Butternut or Catamount Ski
2. Manchester, Vermont
Why it’s on the list: Can you say charming?! This village in southern Vermont 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.
Here’s a post I wrote all about it ➡️✨ Winter Weekend Guide for Manchester, VT✨ so you can plan the perfect trip and pick out everything from where you’ll stay to where to eat. (so many choices!)
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.
Indoor Winter Activities 🖼🎄
- Museum of the Creative Process
- The American Museum of Fly Fishing
- Tour Hildene, the Lincoln Family Home
- Shires’ Holiday Inn Tours
🎿 Outdoor Winter Activities 🥾
- Spots to hike or snowshoe in Manchester
- Ski/ride at Stratton Mountain Resort or Bromley Mountain
3. Woodstock, Vermont
Why it’s on the list: “When you visit Woodstock, you’ll uncover a place that’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 Woodstock’s village, inspiring visitors to discover the creative treasures that lay waiting.” ~woodstockvt.com
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 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.
🎄 Indoor Winter Activities 🖼🎄
- World-renowned Spa at Woodstock Inn & Resort
- American Precision Museum
- Marsh-Billings-Rockefeller National Historical Park Tours
- Ice skate at Union Arena
🎿 Outdoor Winter Activities 🥾
- A Forest of Lights, Magical Forest Canopy Walk
- Annual Wassail Weekend; a celebration of the sights, sounds, and spirit of winter
- Multiple scenic hikes in Woodstock
- Snowshoe or nordic skiing, or downhill skiing Saskadena Six Ski Area
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!
If planning a trip to Litchfield, here’s a link to a post I wrote about the best inns to stay in Litchfield County!
🎄 Indoor Winter Activities 🖼🎄
- Litchfield Distillery
- the nation’s first law school at Tapping Reeve House and Litchfield Law School
- 🧖 The Spa at Litchfield Hills
🎿 Outdoor Winter Activities 🥾
- Walk, snowshoe, or cross-country ski at White Memorial Conservation Center
- Ski or snowboard at Mohawk Mountain
- Choose a hike in Litchfield
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
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!
🎄 Indoor Winter Activities 🖼🎄
- Kent Coffee & Chocolate
- Visit Kent Falls Brewing Co
- Connecticut Antique Machinery Association Museum
🎿 Outdoor Winter Activities 🥾
- Ski Mohawk Mountain
- Kent Falls State Park, CT’s tallest waterfall!
- Hike Connecticut’s Appalachian Trail
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 (6288’) since 1869. Up to Mount Washington, that is!
🎄 Indoor Winter Activities 🖼🎄
- Visit RiverWalk Resort at Loon Mountain
- Visit Santa’s Village
- Living Shores Aquarium
- Visit, stay, or eat at the historic and famous Omni Mount Washington Resort
🎿 Outdoor Winter Activities 🥾
- Winter train ride up the tallest mountain in the Northeast on The Cog
- Franconia Village Cross Country Ski Center
- Ski, tubing, or “Snow-Go’ at Loon Mountain
- Explore the Ice Castles
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 is also a town named a top 20 getaway in New England by Travel + Leisure Magazine
Running list of White Mountain holiday activities here.
🎄 Indoor Winter Activities 🖼🎄
- Shop tax-free at the Settler’s Green Outlet Village; local hand-craft, antique and gift shops!
- Drive the famous Kancamagus Scenic Highway
- Visit Mount Washington Observatory Weather Discovery Center
- Live music, dining, and more at Cranmore Mountain Lodge
🎿 Outdoor Winter Activities 🥾
- All aboard the Conway Scenic Railroad for Santa’s Holiday Express or the Snow Train
- Take a horse-drawn sleigh ride!
- See the frozen Diana’s Baths Waterfalls, 1.3 miles (Easy)
- Tubing, 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.
| 🎄 Indoor Winter Activites 🖼🎄 | 🎿 Outdoor Winter Activities 🥾 |
| 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 Spa | See 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 here | The famous 3.5 mile Newport Cliff Walk |
| Check out the unique shops along cobblestone Thames Street | Other 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.
| 🎄 Indoor Winter Activites 🖼🎄 | 🎿 Outdoor Winter Activities 🥾 |
| Visit Mass MoCA (museum of contemporary art) | Hike Mount Greylock, the tallest mountain in Massachusetts! |
| Visit The Clark Art Institute | Project Snowshoe (snowshoe outside The Clark museum’s 140 serene acres!) |
| Visit Bright Ideas Brewing | Hike the Cascades Trail to a beautiful waterfall, 2.2 mi (Easy) |
| Images Cinema; an independent 501c3 movie theater | Cross-country ski or snowshoe at Stump Sprouts Cross Country Ski Center |
| Catch a show at Berkshire Theater Group | Ski Berkshire East |
10. Portland and Freeport, Maine
MarthaStewart.com named this area one of “The Most Charming Small Towns to Visit During the Christmas Season”. She says, “There’s simply no better place to do your Christmas shopping than in Freeport, Maine.”
Food lovers will delight in a winter getaway to Portland, Maine, where you can indulge in the town’s thriving culinary scene. From lighthouse exploration to ice skating and cross-country skiing, there’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.
| 🎄 Indoor Winter Activites 🖼🎄 | 🎿 Outdoor Winter Activities 🥾 |
| All aboard! Polar Express Train Ride | Attend the Sparkle Celebration; Maine’s most popular holiday celebration (first half of December) |
| Portland Museum of Art | Ski at Sunday River |
| Visit one of Portland’s numerous historic landmarks and Ports | Moose watching tours or guided hikes with Northeast Whitewater |
| Visit Southworth Planetarium | Back Cove; Portland’s very own outdoor exercise rink |
| All other indoor activities listed here | Baxter 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. 😍
