Magical Weekend Getaways from Boston in Winter

Boston at night harbour

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The best weekend getaways from Boston in winter offer a more idyllic version of the colder climes. Just think of romantic weekends spent cuddled up in rustic cabins or fabulous weekend getaways with your friends for skiing (or just drinks).

If you live in New England, you probably have feelings about winter.

Love it or hate it, you have to live with it!

Escaping the city means you can enjoy picturesque landscapes draped in snow blankets, rather than trudging through the sloshy grey leftovers from yet another storm.

Hit the slopes, enjoy winter festivals, or just explore some fascinating small towns in New England to shake up your winter weekends.

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Tips for Winter Weekend Getaways in New England

If you’re not a local but looking to add a weekend getaway from Boston during your visit to the city, there are a few things you should keep in mind.

First and foremost: public transportation is not excellent around Boston. In fact, it hardly exists.

So you’ll most likely want a car to get wherever you’re going. That’s not a huge deal, except that winter is a dodgy time to drive if you’re not familiar with ice and snow.

If you feel comfortable getting behind the wheel regardless of the weather, then rent a car for the weekend.

Just make sure you have at least the standard emergency equipment for winter (ice scraper, shovel, blankets, and de-icer).

If you’re taking a weekend trip from Boston to one of the region’s other city hubs, you could take a look at Amtrak options.

The train from Boston to Portland, Maine, for example, is a lovely scenic route!

Finally, note the holidays will typically cause prices to rise. Winter holidays include:

  • All the December holidays
  • New Year’s Eve + Day
  • A long weekend in January (Martin Luther King, Jr Day)
  • A long weekend in February (Presidents’ Day)

Schools typically close for a week in February around Presidents’ Day, so this can be a more expensive time to travel.

It’s a common family vacation break for ski holidays, too, so you’ll want to book early if you plan to hit the slopes that week!

Weekend Getaways from Boston in Winter

There is an abundance to choose from if you’re super into all things snow and ice.

Think skiing — both the downhill and cross-country varieties. Or maybe think of other winter favorites like snowboarding, sledding, and ice skating.

One winter, I even played with bumper cars on ice in Providence!

If you’re not into the cold-weather activities (I’m 100% with you), getting out of the city can still rejuvenate you.

Boston skyline

Check out some of New England’s smaller cities and quaint small towns. Enjoy local, independent shops and cafes.

Winter is a great time to explore more locally, saving up those precious vacation days for better weather adventures!

Whatever winter adventures you love, they’re all just a short drive from Boston for a perfect weekend getaway.

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Top Skiing Spots Near Boston

If you’re ready to hit the trails, there are tons of places to ski near Boston.

Several are within just about an hour’s drive of the city, so you could definitely do it on a day trip.

But if you want a weekend getaway from Boston in winter, what better way than to shack up at a ski resort for fireplaces and drinks?

Boston ski resort

With varying degrees of difficulty and available amenities, these are the top skiing spots near Boston for a weekend getaway:

  • Loon Mountain, NH
  • Waterville Valley, NH
  • Attitash, NH
  • Killington, VT
  • Jay Peak, VT
  • Sugarbush, VT
  • Stowe, VT
  • Mt. Snow, VT
  • Sunday River, ME
  • Shawnee Peak, ME
  • Wachusett, MA
  • Ski Butternut, MA

Special Events for Weekend Getaways from Boston in Winter

1. Newport, RI

Head to Newport around the holidays in December to see all the mansions decked out.

There are often carolers or other live performances of festive shows, so plan your weekend getaway accordingly!

In February, Newport hosts the annual Newport Winter Festival, which they call New England’s largest winter extravaganza!

Newport RI Mansion Near Boston New England

2. Kennebunkport, ME

Visit for the December events included in Christmas Prelude, or wait until February to Paint the Town Red.

Kennebunkport really leans into the romance around Valentine’s Day, so you can expect lots of couple’s activities, champagne, and oysters galore.

3. Portsmouth, NH

Portsmouth is perfect for a classic New England winter weekend getaway. Check out its Vintage Christmas events in December.

4. Woodstock, VT

The Woodstock Snow Sculpture Festival, held around Presidents’ Day Weekend every February, is definitely worth a visit!

Just note that it’s weather-dependent and could get canceled. #WinterWoes

5. New Castle, NH

I have three words for you: Winter Wine Festival.

Beat the winter blues with some deep, luscious reds and effervescent whites.

It’s held annually between January and February at Wentworth by the Sea.

The Boston Wine Festival takes place from January to March annually, but why not enjoy a weekend getaway from Boston for this one instead?!

» Related | Christmas Things to Do in Chicago

Small Towns & Cities for Weekend Getaways from Boston

New England is filled with small towns built up around that classic concept of Main Street.

Church steeples rising above the rooftops can be spotted from miles away as roads twist and turn along the landscape.

There are also plenty of smaller cities that offer lots of amenities without the highrises (and resulting wind tunnels in January…brrr).

Take a weekend away from Boston for some of these iconic small-town vibes and smaller city explorations.

Main Street New England

Check out these recommendations:

  • Stowe, VT
  • Woodstock, VT
  • Burlington, VT
  • Stockbridge, MA
  • Northampton, MA
  • Plymouth, MA
  • York, ME
  • Kennebunkport, ME
  • Portland, ME
  • Providence, RI
  • Hartford, CT

Heading Farther Afield for a Winter Weekend Trip

Want to really get away from it all? Hide out in a cabin in the mountains, try to blend in as an off-season tourist, or just flee the country altogether!

Escape the urban hustle for a complete reprieve in any of these locales:

  • The Catskills, NY – As featured in The Marvellous Mrs Maisel
  • The Berkshires, NY
  • Adirondacks, MA

My personal favorite?

Head to Acadia National Park and Bar Harbor, Maine

This area is simply stunning no matter the time of year. Try cross-country skiing or just enjoy the quiet of off-season travel to an otherwise busy tourist destination!

Acadia features in our East Coat National Parks guide too.

Want an international escape? The joy of living so close to the Canadian border means you can actually do a long weekend getaway from Boston.

I do recommend a 3-day weekend for two reasons:

  1. Longer drives deserve longer stays
  2. Canada doesn’t celebrate the same holidays so you can maximize your day off without paying holiday weekend prices! (This actually only applies to January, since Family Day in Canada overlaps with Presidents’ Day in the USA.)

Head to Montreal or Quebec to enjoy a different city vibe. In winter, there’s some sort of magic to the enchanting Old Quebec cobblestone streets.

Drive there in about 6 hours, or take a quick flight if you’d prefer to avoid the winter roads.

If you prefer warmer temps with your tinsel, check out our guide to sunny winter vacations in the US.

Quebec at Christmas

Pin to your Boston planning board for later!

Looking for the best Boston day trips in winter? Visit snow-capped nature, crowd-free historic towns and hit the slopes of Boston's best getaways!

Do you have favorite weekend getaways from Boston in winter that I missed? Tell me in the comments!

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