6 New England Winter Getaways

By Kelley Boymer
18 Jan 2022

What is more idyllic than a New England winter getaway? Straight out of a lifetime movie– your adventure may entail skiing the slopes, window shopping in small towns, or sipping a hot toddy by the fireside of a rustic B&B. The Northeast is a wonderful place to visit during the colder months. New England’s six states: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire and Maine each have plenty of unique and fun sights and activities. Whatever your magical winter vision may be, you can make it a reality with some of these New England winter getaways.

6 New England Winter Getaways

Vermont in snow - Click. Read. Love. 12.17.21

Woodstock, Vermont


So we may be a little biased, but Vermont is the best when it comes to quintessential New England winter getaways. Ski mountains, quaint towns dressed in twinkling lights and a fresh layer of snow. Hiking, snow-shoeing, nordic skiing, cozy rustic dining and lodging– what more could you ask for? Vermont is the outdoor adventure enthusiast’s playground. And what better small town to choose than our very own Woodstock, Vermont. It has a little bit of something for everyone– whether it be downhill skiing, nordic skiing, snowshoeing shopping, or dining that you desire. 

Check out Jess’s Woodstock Travel Guide for more details about where to stay, eat and what to do.

Other Vermont Getaways: 

Bethel, Maine

Looking for a similar Woodstock vibe but in a Maine setting, look no further than Bethel. Also known as, “this side of paradise” Bethel is more of a rustic take on the quaint small town thing that Woodstock has going on. Begin your getaway by checking in to the Bethel Inn and Resort (comparable to the Woodstock Inn) and set out to hit the slopes at the local family friendly ski mountain– Sunday River Ski Resort or Carter’s X-C Ski Center. If skiing isn’t your thing, start your day in Bethel hiking and exploring in Grafton State Park, then cruise on over to Sunday River Brewing Company for lunch and a beer. Whatever it is that you enjoy, Bethel offers a range of activities. 

WHAT TO DO in bethel during winter

Grafton State Park

Cross-country skiing, snowshoeing, snowmobiling and hiking– options are endless in Grafton State Park.

Sunday River Ski Resort

870 skiable acres, 135 trails & glades, 2,340 vertical feet and 18 lifts.  Sunday River is known for having reliable snow excellent with a variety of trails for beginners and experts.

Carter’s X-C Ski Center

Carter’s offers nordic skiing, fat biking and snowshoeing the whole family can enjoy– check their website for daily snow conditions.


Millbrook Tavern

Located in the Bethel Inn and Resort, this comfortable, casual, family friendly dining offers both indoor and *COVID friendly outdoor dining with fire pits and heated igloos. 

Sud’s Pub

If pub grub, pizza and beer is your thing– Sud’s is your spot.

Modern Barn

Featuring delicious American fare, Modern Barn is known for it’s excellent wine list and cozy atmosphere.

Butcher Burger Bethel

This butcher is doing their part using locally sourced ingredients and composting donating food waste to a local farm. At Butcher Burger Bethel you will find burgers, sandwiches, munchies and the best of Maine beer.

Sunday River Brewing Company

Good pub food and classic brewery vibes. A great place to stop after hitting the slopes.

where to stay in bethel during winter

Bethel Inn and Resort

A premier resort where you can get all the amenities for both luxury and adventure. Comparable to the Woodstock Inn, this resort includes 40 km of nordic ski trails, fat tire biking, horse drawn sleigh/wagon rides, skating, outdoor heated pool, health club, spa services, restaurants, and is just under 7 miles from Sunday River Ski Resort. It’s also dog friendly if you want to bring your pup along for the trek. 

Grand Summit Hotel & Jordan Hotel

Affordable options for a getaway that’s more about the adventure than the stay.

Jackson, New Hampshire

Nestled in the heart of the White Mountains, Jackson, New Hampshire is another beautiful resort town with all the amenities to make your outdoor getaway well worth your while. 

WHAT TO DO in Jackson, NH During Winter

Jackson Ski Touring Foundation

Offering over 50 trails and 100 km for both cross country skiing and snowshoeing.

Nestle Nook Farm

This gorgeous farm provides a little bit of everything from sleigh rides and ice skating to snowshoeing.

Wildcat Mountain

Known for it’s breathtaking views and incredible terrain, ski Wildcat!

where to EAT

J-Town Deli

Perfect for breakfast, lunch and dinner on the go!

Shannon Door

Traditional Irish pub fare and live music.


Classic, homestyle breakfast and lunch.

Red Fox Bar & Grille

Traditional American fare for both lunch and dinner with authentic wood fire grilling.

where to STAY in jackson, nh

Inn at Ellis River, The Snowflake Inn & The Inn at Thorn Hill Spa

For a more intimate, romantic getaway, snuggle up by the fireside and enjoy a jacuzzi tub at one of these charming inns.

Eagle Mountain House

This beautiful, historic hotel was voted the best cross country skiing in the east!

Newport, Rhode Island

What’s not to love about Rhode Island in the winter? There is something magical about the cobblestone streets, bustling shops, bars and pubs overlooking a rough rocky shore in the dead of winter that feels refreshing. If your choice of adventure is more of a shop, eat, drink kind of style, then Newport is exactly what you need in your life. 

Check out Jess’s Newport Travel Guide for hundreds of recommendations for where to stay, what to do, and where to eat in Newport with 3-day itineraries and tips from a local.

Boston, Massachusetts

Are you a country mouse looking for a change in scenery? Boston is a great, manageable city that can be both family friendly or provide a romantic getaway for two. Enjoy everything from broadway shows and shopping to fine dining and beautiful hotels. Another plus for Boston, you may find cheaper rates during the winter months.

what TO DO in boston, ma during winter

The Freedom Trail

Walk the Freedom Trail to learn about over 250 years of American History starting with the American Revolution and beyond. Pick a tour that interests you most along the 2.5 mile red line. This one caught our eye… Revolutionary Women

Museum of Fine Arts, The Boston Tea Party Ships & Museum & Boston Children’s Museum

Boston has a fantastic selection of museums whether it is art, history or amusement for the whole family that you are looking for.

Boston Common Frog Pond

There’s something magical about skating in the city and this is the perfect place to do it!

The Boston Opera House & Colonial Theatre

The best of theater and movies in the city!

The Prudential Center

Stay out of the cold and enjoy shopping and restaurants in the Prudential Center. Some favorite shops: Madewell, Paper Source, Sephora & Saks Fifth Avenue. 

TD Garden

Sports fans can head to TD to enjoy the excitement of a Celtics or Bruins game.

Old Town Trolley Tour

The Trolley Tour is a great way to see the best of Boston in a short amount of time. Not only do you have the opportunity to hop on and off at your leisure but you also get enjoy hearing stories about the different locations as you go.

Boston Seaport | Snowport & Frostbite Racing

Curling and Sailing in the Winter? Look no further than Boston Snowport and Frostbite Sailing. 

where to EAT

Galleria Umberto for pizza on the go or Carmelina’s for fresh Sicilian pasta and seafood with a Mediterranean twist

If it’s Italian food you desire, you can’t go wrong in Boston’s North End. Other noteworthy splurges in Italian dining- Sorrellina and Table Boston


New American described as “refined yet playful.”

O Ya

Contemporary Japanese striving for freshness, quality and variety.

Barcelona Wine Bar

Tapas bar inspired by Spanish and Mediterranean cuisine with one of the best Spanish wine bars in the country.


Mediterranean seafood in a sophisticated setting in Back Bay.

Atlantic Fish Company

Some of Boston’s best seafood in the Back Bay.

Ma Maison

Satisfying French cuisine, a boutique wine list and exciting cocktail menu.

where to STAY in boston, ma during winter

Omni Boston Hotel at the Seaport

Located in the center of the bustling Seaport District this hotel has a clean, modern appeal and includes restaurants, amenities and spa services.

Fairmont Copley Plaza

Eco-certified and centrally located in Boston’s historic Back Bay. Also home to OAK Long Bar and Kitchen.

The Lennox Hotel

The Lennox prides itself in local partnerships, hip vibe and will make you feel at home with comfortable and contemporary accommodations.

The Newbury Hotel & Boston Harbor Hotel

Splurge worthy hotels with elegant decor, luxurious dining and amenities and gorgeous views.

Hartford, Connecticut

History buffs will delight in a getaway to Hartford, Connecticut. From museums to historic homes– the Mark Twain House and Harriet Beecher Stowe Center – what better way to learn about history than experience it yourself? Hartford also offers a diverse range of eateries, lodging and shopping to enjoy during your stay.

what to do in hartford, ct during winter

Wadsworth Atheneum

Featuring a collection of over 50,000 pieces of artwork spanning over a 5,000 years, the Wadsworth prides itself in art and cultural excellence.

The Bushnell

A beautiful setting to see both shows and concerts with “striking art-deco interior and state-of-the-art equipment, production and support capabilities.”

Mark Twain House & Harriet Beecher Stowe Center

For literature fans there is no better way to experience history than with one of the best at the Mark Twain House where he wrote his most famous works of art.

Real Art Ways

An alternative multidisciplinary arts venue for showcasing the arts in all forms.

Elizabeth Park

“Offers just over one hundred acres of formal gardens, green space, recreational facilities, walking loops, and the Pond House Café.” Look out for the Elizabeth Park Conservancy flower show in mid-March, just in time for those winter doldrums to really be setting in.

Bushnell Park

Enjoy ice skating and carousel rides at this historic park.

Hartford Prints!

Three sisters got together to bring this urban goods brand to life with the motto, “handmade and homegrown.”

The Jumping Frog

A locally cherished used bookstore, ahhh I can just smell those well-loved books now.

where to eat

Story and Soil Coffee

All the specialty coffee and tea your heart desires.

Hog River Brewing

Family run craft brewery, the perfect spot to relax and enjoy a delicious brew.

City Steam Brewery

Brewery and restaurant with American pub fare.

where to stay in hartford, ct during winter

The Goodwin Hotel

Classic meets modern at this boutique hotel in the heart of the city.

The Connecticut River Valley Inn

A historic boutique inn with a contemporary twist and personalized touches.

New England Weather & What to Pack

Weather in New England is unpredictable, that’s why layering and bringing a little bit of everything is always your safest bet. If you are traveling by car you have the advantage of packing it full (as I often do so as never to feel unprepared). If you travel on the lighter side be sure to bring hat, mittens, jacket(s) and appropriate, comfortable and warm footwear that is suitable for all the elements (rain, snow, sleet) and walking of course. Check out Jess’s Snow Gear for Women and the Best Insulated Jackets to be sure you are both prepared and fashionable on your winter getaway.

COVID Guidelines

As with any travel during these COVID times, you take the risk of increased exposure in a place that will most likely be busy with others looking to escape their everyday life. Choose activities that you feel comfortable with and look for opportunities to be outside and away from crowds. Be sure to check websites for guidelines, bring your vaccination card and be respectful and responsible by masking up. 

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  1. Fawne wrote:

    This is such a great list!!!!! Saving for the perfect winter getaway! Thank you!!!!

    1.18.22 | Reply
    • Thank you, Fawne. I hope you can get away to enjoy one of these spots soon!

      1.19.22 | Reply
  2. Sarah wrote:

    This is a great list, although I would quibble with the food choices in Boston. I think there are more exciting restaurants to try here. Boston has a flourishing food scene, COVID notwithstanding–I’d recommend checking out in Boston: Fox & The Knife, Chickadee, Haley Henry. If you’re willing to go a littler farther afield to Cambridge or Somerville: Pammy’s and Sarma.

    1.18.22 | Reply
    • Thank you for your food recs, Sarah! We will check these out and maybe add them to the list in the future!

      1.19.22 | Reply