Massachusetts in Winter: Things to Do, Places to Visit, and More

Thinking of visiting Massachusetts in the winter?

Massachusetts is known for its beautiful beaches, fresh seafood, and historic colonial towns. While people often choose to visit in the warmer spring, summer, and fall months, if you can handle the cold, Massachusetts is a wonderful place to travel in the winter as well.

Keep reading for tips on the best things to do and places to see during a winter trip in Massachusetts!

Visiting Massachusetts In Winter

Massachusetts has many noteworthy places to visit, but one of the most popular destinations is, of course, the capital city of Boston. And it’s for good reason, too. It’s a vibrant city with plenty of things to do in any season.

In this post, I mention many places outside of Boston as well, but you’ll notice several activities centered in Boston or the surrounding areas simply because there is so much to do there.

Massachusetts in winter: Boston's Back Bay neighborhood

Is Boston worth visiting In winter?

There is something so romantic and festive about Boston during the chilly, winter months, especially around Christmas and New Year’s.

The city lights up for the holidays and features several festivals, a historic tree lighting in Boston Common, and much more. (Keep reading to learn more about all there is to do in Boston in the winter!)

Parking in Boston can be a big pain in the winter, however, so I recommend either flying into Boston or parking your car outside of the city and using public transportation to get around.

If you do plan to fly to Boston, note that snow storms are fairly common and there could be flight delays or cancellations.

All in all, if you dress for the weather, Boston is a great place to visit in the winter. You can tour all the historic sights while avoiding all the crowds that appear during warmer months.

How do people survive winter In Massachusetts?

It’s true that winter in Massachusetts is usually very cold and snowy, but that doesn’t mean you can’t still have fun! There is a host of activities to get you through the long winter months.

To make a winter trip to Massachusetts more enjoyable, there are two general tips to keep in mind:

Wear layers

I once heard someone say that you can handle any type of weather if you are properly dressed, and there is some truth to that.

Bundle up with a warm coat, hat, scarf, gloves, thermal underwear, thick socks, and boots, and you can comfortably enjoy walking outdoors in Massachusetts in the winter.

Keep your car stocked and ready

If you plan to drive to Massachusetts, it’s a good idea to schedule a tune-up for your car to ensure you won’t have any breakdowns in the unpredictable winter weather. Getting stuck in the middle of a snow storm does not sound very fun.

No matter what, it’s a good idea to have a snow scraper, blankets, a flashlight, first-aid kit, and water in your car if you do happen to get stuck—always better to be safe than sorry!

Best Massachusetts Winter Activities

Here is a list of the best winter activities to do in Massachusetts:

1. Go ice skating at an outdoor rink

The Boston Common Frog Pond is an iconic place to go ice skating in the winter.

In spring, summer, and fall, the Frog Pond is a favorite spot for kids to splash in the fountains or for families to catch an outdoor movie on the big screen. But in the winter, the water freezes to become an ice skating paradise.

⛸ Admission to the Frog Pond is $8 per person, plus $15 for skate rentals ($10 for kids’ rentals). Tickets are only available on site, not online.

The Ice Rink at MGM Plaza in Springfield is another popular ice skating option.

The ice rink is one of many entertainment options at the MGM Resort, so you may also find yourself wanting to enjoy a warm drink at the Lions Den, see a show in Symphony Hall, or watch a sports game or concert at the MassMutual Center.

⛸ Admission to the Ice Rink at MGM Plaza is $14 for adults and $10 for kids 12 and under, plus $6 for skate rentals. Tickets are only available on site, not online.

2. Sled down a snow-covered hill

Embrace your inner child by coasting down a big sledding hill in Massachusetts. There are lots of great places to go sledding or snow tubing, but here are a few popular options:

  • Mt. Hood, Melrose: Mount Hood Memorial Park and Golf Course is surrounded by hills that make for the perfect sledding spots in the winter.

  • Hospital Hill, Northampton: This sledding place has variations in steepness that allow you to go as fast or as slow as you want—a great option for both beginner and experienced sledders.

  • Boston Common, Boston: There is a good-sized sledding hill leading down from the Soldiers and Sailors Monument. Combine sledding with ice skating at the Frog Pond nearby for a day of outdoor winter fun!

  • Prospect Hill Park, Waltham: Catch a beautiful view of the Boston skyline in the distance from the top of this sledding hill.

  • Cable Hill County Road, Ipswich: This is another local favorite on the North Shore of Massachusetts.
Winter in Massachusetts: Sledding down a snow-covered hill

Photo credit: Brendan Beale, Unsplash

3. Ski the day away

For more snowy fun, consider a day of skiing at one of Massachusetts’ ski resorts, including:

  • Wachusett Mountain: This resort boasts 27 trails, 6 lifts, and a 2,006-foot summit. It is one of Massachusetts’ most accessible ski resorts, with an adaptive program to assist skiers with special needs.

  • Jiminy Peak: This is the largest ski and snowboard resort in southern New England, located in the mountainous Berkshires region of Massachusetts. This resort includes lodging options and other activities, including a 3,600-foot mountain coaster.

  • Blue Hills: This ski resort has been in operation since 1950 and is just outside of Boston. It has 16 different trails of varying difficulty, making it a great place for beginner and intermediate skiers.

  • Butternut: This is another popular ski resort in The Berkshires with more than 20 trails ranging from beginner to advanced. There is also a tubing hill on site to enjoy.

4. Enjoy dinner in an igloo

What’s more wintery than eating inside an igloo…albeit an electric, heated igloo? 😉 There are several places where you can enjoy this unique dining experience in Massachusetts.

Just note that igloos are quite popular and can get booked up quickly—it’s best to reserve ahead of time!

Here are a few well-rated places with igloo dining:

  • Mile Marker One, Gloucester: Enjoy an igloo at this waterfront restaurant with plenty of seafood options.

  • Lookout Rooftop, Boston: The best part about this place is the amazing views of the city. Note that food and drinks seem to have mixed reviews, and this place can get really crowded.

  • 75 on Liberty Wharf, Boston: This restaurant is right by the water and has better reviews than Lookout Rooftop, but is also at a higher price point.

  • Patriot Place, Foxborough: Patriot Place is a giant dining, shopping, and entertainment complex with a couple restaurants offering igloo experiences.

5. Rent a cozy cabin for a weekend

One of the best things to do in the winter in Massachusetts is simply enjoy time with family and friends indoors, playing games, cooking, or watching movies together.

Why not escape to a cozy cabin for a few days and enjoy the pretty winter scenery from inside?

Here are a few cute places to check out:

Writer's Retreat in Orange, Massachusetts
Writer’s Retreat in Orange, Massachusetts | Credit: Patti, homeowner

6. Walk along the beach

Sure, you may not want to sunbathe or go swimming in the winter, but walking along the beach is still a great option. Bundle up well, and enjoy one or more of Massachusetts’ beautiful sandy beaches.

Here are a few great beaches to explore:

Winthrop Beach, Massachusetts

7. Explore small-town shops and cafes

Massachusetts is filled with quaint, historic towns that make you feel like you stepped back in time. In the winter in particular, there is something magical about sitting in a cozy cafe while watching snow lightly falling outside.

Some of my favorite small towns include Concord, Marblehead, and Stockbridge.

Keep scrolling to learn more about these towns and other nice places to visit in Massachusetts in the winter.

8. Ride in a dog sled

For a one-of-a-kind winter experience, book a sleddog tour with Hilltown Sleddogs.

Hilltown takes great care of their Alaskan Huskies and loves to share their mushing passion with others. When you book a tour, you get to meet all the dogs face-to-face, learn how to harness them properly, and then enjoy a scenic ride through the woods.

🐕 Tours last 1.5 hours and cost $300 for two people, plus $125 for each additional adult. (There are significant discounts for kids, and those under age 4 get to ride for free.)

9. Experience Boston’s food scene

Boston has an amazing assortment of restaurants to choose from, with something to satisfy any palette. What better way to spend chilly winter days in the city than to hop from one cozy restaurant to the next?

Here are some great options:

  • Union Oyster House: This historic restaurant has been in operation since 1826 and is a one-of-a-kind place to order oysters when in Massachusetts. The interior decor alone is worth a stop inside.

  • Saltie Girl: Founded by a native New Englander who grew up on a sailboat with her dad, Saltie Girl celebrates the natural flavors of the sea, with raw and fried oysters, clams, lobster, and more. This is a must-stop place in Back Bay if you’re a seafood lover.

  • Monument: Located in Charlestown, this rustic chic restaurant features “creative comfort food,” with items such as kung pao Brussels sprouts and lemon-rosemary chicken. They also are known for their delicious brunch menu, with their popular lemon poppyseed buttermilk pancakes.

  • The Q: For authentic Chinese hot pot and other dishes, The Q in Chinatown is a great choice. Customers rave about the great service and food quality. What sounds better than hot pot on a cold day?

  • Modern Pastry: I am told this place has the best cannolis in all of Boston, which are filled to order. It’s located in the North End, also called Boston’s Little Italy.

  • The Helmand: This restaurant is in Cambridge but worth hopping on the red T line to get here. It’s an authentic Afghani restaurant with a delicious menu of chicken kebabs, roasted lamb, saffron rice, fresh bread, and much more. It’s a bit overpriced but the food quality is good and is something different to experience.

Best Places To Visit In Massachusetts In Winter

While these places are nice to visit at any time of year, there is something special about seeing them in winter. Crowds dissipate, and there is a sort of sleepy magic in the air.

📍 Boston

A visit to the Massachusetts state capital is a must for your winter itinerary. There is a never-ending list of things to in this city, but below are a few places to start!

Best places to visit in Boston:

  • North End: Known as Boston’s Little Italy, the North End is where you can taste authentic Italian food.
  • Freedom Trail: Walk this 2.5-mile marked path that leads you to 16 historic sites that played a key role in the American Revolution.
  • Faneuil Hall Marketplace: This popular shopping area is called the Cradle of Liberty because patriots would meet here in the days leading up to the Revolutionary War.
  • Chinatown: Enjoy delicious food in a center of Asian-American life in New England.
  • Newbury Street: Shop along this popular street and be sure to also walk over to the Boston Public Library.
  • Boston Common and Public Garden: These adjacent parks are a must-see when visiting Boston and are beautiful to walk through even in winter.
  • Beacon Hill: This is one of the most picturesque and historic areas of Boston, including the beloved Acorn Street with its original cobblestones.

See my 24 hours in Boston post for more details on what to do in Boston!

Beacon Hill, Boston

Where To Stay In Boston

Hyatt Regency Boston Harbor: Mid-range hotel with nice views of the Boston Harbor.

Omni Parker House: One of Boston’s most iconic and historic hotels, in operation since 1855.

📍 Concord

Concord is a quintessential, small New England town just outside of Boston, filled with boutique shops, cafes, and historic homes, and churches.

It looks like it belongs in a postcard, especially during the festive holiday months with the twinkling lights and lightly falling snow.

Concord is historically significant for the Battles of Lexington and Concord in the Revolutionary War, as well as Walden Pond made famous by author Henry David Thoreau.

Best things to do in Concord:

Concord, Massachusetts

Where to stay in Concord

Residence Inn by Marriott Boston Concord: This hotel is just a few miles from Minute Man National Historic Park and offers free bikes to its guests.

Concord’s Colonial Inn: Stay in this historic 1716 hotel in Monument Square.

📍 Marblehead

Also not far from Boston is the quiet coastal town of Marblehead. The town will once again have you feeling like you stepped back in time, with its narrow streets and 17th-century buildings.

Best things to do in Marblehead:

  • Bundle up and head to Castle Rock Park, which you can easily miss if you aren’t looking for it. The small park gets its name from the castle-like mansion nearby. Climb to the top of the giant rock at the edge of the park for panoramic views of the ocean.
  • Stop by Shubie’s Marketplace for a tasty lunch. They have a large deli counter serving fresh sandwiches.
  • Then walk around downtown Marblehead to browse through boutiques and admire the storied architecture.
Massachusetts in winter: Castle Rock Park in Marblehead

Where to stay in Marblehead

Harbor Light Inn: This boutique hotel is in the heart of the historic Marblehead town center and is just steps away from the ocean.

The Hotel Marblehead: Another historic inn minutes from the beach and in a centrally located residential area.

📍 Stockbridge

The historic town of Stockbridge is located in the scenic Berkshires highlands and is best known as the former home of iconic American artist Norman Rockwell.

During Christmas time in particular, the town recreates the magical scene Rockwell painted of Stockbridge’s Main Street at Christmas.

Best things to do in Stockbridge:

  • Order lunch at Main Street Cafe, which is in the old Stockbridge General Store building and still maintains a lot of the original interior. Then browse the rest of the shops along Main Street.
  • Visit the Norman Rockwell Museum to learn about Rockwell’s life and view many of his paintings.
Norman Rockwell Museum, Stockbridge

Where to stay in Stockbridge

The Inn at Stockbridge: This bed and breakfast has stylish rooms with private bathrooms, offering a full breakfast and complementary snacks.

The Red Lion Inn: This historic hotel is full of character and charm and right on the main street of downtown Stockbridge.

📍 Rockport

Rockport is another scenic coastal town on the north shore of Massachusetts, about an hour from Boston. For a taste of seaside life in New England, this town is the perfect choice.

Best things to do in Rockport:

  • Watch a performance at the Shalin Liu Performance Center. Rockport is known for its music culture, and the Performance Center is a hidden gem for lovers of jazz and classical music.
  • For a picturesque harbor scene, visit Motif #1, an iconic red fishing shack that’s been a favorite subject for painters for decades.
  • Go for a walk on Long Beach, where you can catch beautiful views of coastal cottages and the Twin Lighthouses in the distance.
  • Shop along Rockport’s Main Street and Bearskin Neck for unique gift shops, craft stores, and cafes.

Where to stay in Rockport

Addison Choate: Enjoy a blend of old and new at this boutique hotel that’s a 5-minute walk from Front Beach.

Sally Webster Inn: This artfully decorated bed and breakfast is within walking distance from the galleries and shops of central Rockport.

Massachusetts in winter: Scenic New England town

📍 Plymouth

Plymouth is known as the site of the first Pilgrim settlement in the U.S. in 1620. If you enjoy history, there is a plethora of sites to check out here.

Best places to see in Plymouth:

  • Plimoth Patuxet Museums: See a recreation of a 1627 Pilgrim village, where you can learn about early English settlers and the Indigenous people who lived in the Plymouth colony in the 1600s.
  • Plymouth Rock: See the rock that marks the place where the first Pilgrims were said to have arrived from across the Atlantic.
  • Mayflower II: See a full-size replica of the original Mayflower ship that brought the Pilgrims to the Plymouth Colony in 1620.

Where to stay in Plymouth

Thomas Sea Suites at Harbourtown: Spacious rooms not far from the Plimoth Patuxet Museums.

Mirbeau Inn and Spa: If you’re looking for luxury, you might enjoy staying in this modern castle.

📍 Cape Cod

Cape Cod is a prime vacation destination in the summer, but you can snag lower accommodation costs and enjoy fewer crowds if you opt to visit in the winter. The stunning ocean views are the same no matter the season!

And the interesting thing about the weather on Cape Cod is that the bay water warms the peninsula more than on the mainland. Daytime temperatures average around 40 degrees Fahrenheit in the winter, so not as bitter as you might think.

Fun things to do on Cape Cod:

  • Visit the Sandwich Glass Museum, founded in 1825 and featuring a wide array of rare glass.
  • Explore unique shops and cafes in towns along the Cape, including Falmouth, Woods Hole, Brewster, and Provincetown.
  • Go lighthouse hopping to see as many of the Cape’s 14 lighthouses as you can, including Nobska Light in Falmouth, Chatham Light in Chatham, and Race Point Light at the very tip of the Cape in Provincetown.
  • Drive along the Cape Cod National Seashore and stop by the Salt Pond Visitor Center that’s open year-round.
  • Starting at the Visitor Center, walk the scenic 1.3-mile Nauset Marsh Trail, which also has a connection trail to the famous Coast Guard Beach.
Massachusetts in winter: Scenic coastal landscape

Where to stay in Cape Cod

Candleberry Inn on Cape Cod: Cozy bed and breakfast in Brewster with beautifully decorated rooms.

Inn on Main: Stay in this historic Cape Cod-style home with spacious rooms and a delicious breakfast.

Winter Festivals In Massachusetts

There are several winter festivals and holiday markets planned throughout the state, starting as early as November and going into February.

Whether you want to celebrate the Christmas season, participate in outdoor games, hear live music, or sample local food and drinks, each of these festivals has something fun to offer:

SoWa Winter Festival Boston

In the South End of Boston is the popular SoWa district known for its art galleries and unique shops.

From the end of November to mid-December, the SoWa Winter Festival takes place inside the SoWa Power Station, where you can browse the offerings of more than 100 makers and food vendors.

Cost: $10 admission at the door
Dates: End of November to mid-December (2023 dates to be announced)

Christmas by Candlelight at Old Sturbridge Village

Enjoy a traditional Christmas experience at Old Sturbridge Village, which is decorated in beautiful, festive decor this time of year.

Watch a nightly lighting ceremony, walk the Christmas Tree Trail and Christmas Wish Bridge, see artisans working on classic Christmas projects, visit Santa, sample sweet treats, and much more.

Cost: $32 for adults, $16 for youth ages 4-17
Dates: November 25, 26, 27, and December 2, 3, 4, 9, 10, 11, 16, 17, 18, 23, 27, 28, 29, and 30, 2022
Register here (registration required ahead of time)

First Night Boston

Ring in the new year at Boston’s annual New Year’s Eve celebration, First Night Boston. See a number of music and other artistic performances in Copley Square, Boston Public Library, and other locations around the city.

This year, ice sculptures surrounding the theme “250th Anniversary of the Boston Tea Party” will be on display in Copley Square as well—definitely a must-see!

Cost: Free!
Date: December 31, 2022, beginning at noon and ending shortly after midnight

Acorn Street in Boston

Northampton Ice Art Festival

Come see the 12th annual Northampton Ice Art Festival. Artists will carve their sculptures during the day on Saturday, January 21 and the finished products will be on display in the city during the first Northampton Winter Festival—happening at the same time as the Ice Art Festival.

Cost: Free!
Dates: Saturday, January 21 and Sunday, January 22, 2023

Lowell Winterfest

Enjoy live music and entertainment, purchase food and gifts from local vendors, and play creative games that are fun for the whole family at the Lowell Winterfest.

Cost: No cost listed on the website, but I believe it is free.
Dates: February 17-18, 2023


Hopefully I’ve convinced you that there’s still a lot to do in Massachusetts in the winter!

From exciting outdoor activities like ice skating, sledding, and skiing to shopping and dining in historic small towns, there’s no shortage of things to entertain during the chilly winter months.

Looking for more things to do in Massachusetts? See 28 Hidden Gems in Massachusetts: Fun for All Ages!

Planning a longer trip through all of New England? Check out The Perfect 7-Day New England Road Trip from Boston.

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