One of my favorite states to visit in New England in the winter is Massachusetts – I love everything about this season in the Bay State, including exploring the coastline in the off-season, to scenic nature walks, to meandering through historic and quaint towns. It really has it all!
Get ready to take some notes and plan the perfect winter in Massachusetts, because this post shares all my tips on the best things to do, places to visit, and winter festivals that are just too fun to pass up. Let’s get started!
What Is Winter Like In Massachusetts?
It actually varies depending on where you visit in the state, which I know surprises a lot of people.
Generally speaking, Massachusetts is cold in the winter, with a high possibility of snow. That said, places along the coastline, especially Cape Cod, tend to be a bit warmer and more mild compared to the rest of the state, and get less snow.
Overall, Massachusetts gets about 50 inches of snow each winter, and it’s also in the top 10 for snowiest states in the entire country. You can expect the most snow in central and western Massachusetts, which includes The Berkshires. In these regions, you can usually expect the coldest weather, too.
General Weather Disclaimer: I always like to point out that weather in New England, while often reliable during each season, can also be very moody and all over the place. Some winter trips I’ve taken to Massachusetts have been incredibly cold and snowy, and others, I almost didn’t even need a coat over my sweater. I always recommend staying on top of weather forecasts a few days before a planned trip or excursion to see what the predictions are.
Is Massachusetts Worth Visiting In The Winter?
I most definitely think so! There’s such a variety of things to do in this state in the winter season that you can plan pretty much any kind of trip you want. And in many popular tourist places in Massachusetts, winter is the off-season, which means you can find awesome hotel deals.
On top of that, Massachusetts is filled with so many incredible things to do that are especially perfect in the winter, including amazing state parks that are gorgeous after a snow fall, awesome museums, skiing and snowboarding, ice skating, creative outdoor dining, and lots of great shopping.
Just keep reading to find out all my favorite things to do this time of the year in the Bay State 😉
Best Places To Visit In Massachusetts In Winter
1. Boston, Of Course!
I mean, it goes without saying that Boston is worth visiting in the winter, right? Winter is the off-season in Boston, too, which means you can often find lots of great rates at hotels, and far fewer crowds at popular places.
Many of the best things to do in the city can easily be done in the colder months, including the Freedom Trail, exploring the shops on Newbury Street, meandering through Beacon Hill and the North End neighborhoods, and exploring the museums and aquarium.
One of my personal favorite things to do in Boston in the winter is to book a food tour. Yes, it’s definitely a bit chilly outside, but I feel like I’m always just more hungry in the winter season, so munching on great Italian food, desserts, pizza and seafood feels especially great this time of the year. These tours are led by local experts, and are a wonderful way to learn about the city’s culinary scene.
Here are some of my favorite food tours in Boston to check out:
North End Pizza Walking Tour: This is my overall best pick for a food tour because it highlights the incredible pizza available in the city, takes you through the charming North End, and also includes a bit of history on the area.
North End Public Market Tour: A very close second is this awesome tour of the North End, which showcases all the best vendors at the city’s public markets.
Psst! I have an entire post on the absolute best food tours in Boston if you want more recommendations!
But beyond food, Boston is filled with awesome wintery things to do as well, including some cool igloo dining, ice skating at Frog Pond, and grabbing a hot chocolate at L.A. Burdick.
Where To Stay In Boston In The Winter:
2. Explore The Quiet Coastline On Cape Cod
It’s no secret that I love Cape Cod, and yep! I’ve been in the dead of winter, which tells you just how much I love it there 😂
Winter is also the off-season for Cape Cod, which means you’ll experience the fewest crowds, have popular places all to yourself, and can enjoy all the gorgeous nature trails and natural beauty of the area at a slower pace. It’s another place where you’ll find some great deals on hotel prices.
The Cape is also a unique place in Massachusetts in the winter season because the weather tends to be a smidge more mild than the rest of the state. Sure, it does snow, and there are very cold days, but you’ll also experience warm(ish), sunny days that are perfect for hitting a nature trail, or a brisk walk on the beach.
While many hotels on Cape Cod are closed in the winter, there are some fantastic places that are open year-round, including the luxurious Chatham Bars Inn, which offers really nice rates in the winter, compared to their peak summer season.
Same goes for businesses on the Cape: some will be closed down for the season, but since it’s a community of over 200,000 year-round residents, plenty of things are also open.
I recommend booking an igloo dinner at Ocean Edge resort in Brewster, visiting the beautiful lighthouses, exploring the shoreline and trails at the Cape Cod National Seashore, meandering through charming Chatham and Provincetown, and splurging on a nice hotel to retreat back to after being outdoors all day.
Where To Stay On Cape Cod In The Winter:
Psst! I have an entire post on visiting Cape Cod in the winter season, if you need some more ideas 😉
3. Visit The North Shore, Too
As much as I love Cape Cod, I also adore the North Shore (rhyme unintended, but I’m going with it!). Just north of Boston along the coast, you’ll find several cute towns that make for either a fantastic day trip in the winter, or a cozy getaway.
One of my personal favorite places to explore year-round is Marblehead. Close to Salem, Marblehead is packed with gorgeous historic houses, great places to eat, a charming little Main Street with adorable shops, and lots of coastal scenery.
In Marblehead, I recommend checking out Shubie’s Marketplace for lunch (and random gift shopping – it’s a great little shop!), Chandler Hovey Park to see the lighthouse, Castle Rock for a stunning coastal sunrise, and getting lost in the historic district. You can also pop into Harbor Light Inn for pre-dinner drinks at their cozy tavern before heading out to Maggie Sail Loft for dinner.
I also highly recommend making a road trip out of the North Shore region. It’s small enough that you can easily plan it for just a weekend, with a one-night stay somewhere. In the longer summer days, you can do it with one day, but because you only have so many hours of daylight in the winter, you’ll probably want two days so you’re not super rushed.
Other great towns along the North Shore to check out are Rockport, Salem, Gloucester, and Ipswich. Rockport is another one of my personal favorites in Massachusetts, and here, you can see Motif 1, which is the most painted building the country. While many shops in town are closed for the season, some places are still open. I have another suggestion in Rockport for you later in the post, so stay tuned for that 😉
Where To Stay On The North Shore In The Winter:
4. Go Shopping In Newburyport
Newburyport is also part of the North Shore region, but I wanted to give it its own section because I feel like in addition to Marblehead, it offers the most to do in the winter season. It also just so happens to be one of my top favorite places for shopping in New England. I absolutely love spending a day or weekend in Newburyport any time of the year.
In the winter season, I love to visit Chococoa Baking Co. to grab one of their special lattes or hot chocolates from their hot chocolate bar, and a seasonal whoopie pie, before I hit up the shops. Market Square in downtown is filled with independent boutiques, and Tannery Marketplace is a short walk away with even more lovely shops.
Plus, the scenery around town feels picturesque, and perfectly New England.
Newburyport also has a fantastic waterfront pedestrian path that’s great year-round, and if you happen to visit on a mild winter day or weekend, you’ll definitely want to drive over to Plum Island, and walk the nature trails around the Parker River Wildlife Refugee (keep an eye out for snowy owls, and more on that later!).
Where To Stay In Newburyport In The Winter:
Here are some of my posts on the North Shore to help you plan even more:
- Best Things To Do In Marblehead, MA
- Best Things To Do In Rockport, MA
- What To Do In Newburyport and Plum Island
5. Cozy Up In The Berkshires
You can’t talk about winter in Massachusetts and not mention The Berkshires, which is a literal playground of winter activities in the colder months. Between great little towns, wonderful museums, skiing, snowshoeing, snow tubing, and endless cozy places to stay, it’s so perfect for the winter season.
Skiing and snowboarding are definitely one of the top activities in The Berkshires in the winter, and you’ll find three big resorts here: Jiminy Peak, Ski Butternut, and Berkshire East.
For an apres ski vibe, Great Barrington and Pittsfield are awesome places visit because they’re filled with fantastic restaurants and great bars for nightlife. For a more low-key afternoon of strolling around, Stockbridge is where to go.
Canterbury Farm is also a wonderful place to check out for ice skating on their pond, as well as hitting up the cross-country and snowshoe trails. There are also some great breweries to check out in the area, including Bright Ideas Brewing and Wandering Star.
Finally, there are some really nice museums in The Berkshires to check out, which are perfect for a cold wintery day, including the Norman Rockwell Museum, and MASSMoCA.
Where To Stay In The Berkshires In The Winter:
❄︎ Chambery Inn
6. Enjoy History In Plymouth
Much like Cape Cod, Plymouth also tends to have more mild weather compared to many place in New England, and it also doesn’t get as much snow (although as you can see from above, it does get the occasional snowfall!). Since it’s packed with incredible history, a lovely little Main Street, and one of the best inns and spas in New England, it’s a great option for the winter season.
While many of the museums in Plymouth are closed in the winter, there are still some nice options for history buffs, including the Richard Sparrow House, Burial Hill Cemetery, and the Mayflower Society House. The Plymouth Center for the Arts is also open in the winter for art-lovers.
And since you could experience some mild winter weather, you can head on over to the local beaches and Pilgrim Memorial State Park for a rejuvenating walk along the coast.
The historic Rye Tavern is a great place for a cozy meal, as this farm-to-table restaurant curates a special winter menu with great craft beers and cocktails, and they also set up heated igloos outside for a very fun experience.
Lastly, Plymouth is home to Mirbeau Inn & Spa, which is one of my favorite places to go when I need a little pampering and R&R. Perfect for a cozy winter getaway, the spa facilities and treatments are all amazing, and every room comes with a fireplace and soaking tub.
Where To Stay In Plymouth In The Winter:
❄︎ Mirbeau Inn & Spa in Plymouth, as mentioned already 😊
❄︎ Hotel 1620
Psst! I have a detailed review on Mirbeau Inn & Spa in Plymouth if you wanted to check that out before booking 😉
Fun Winter Events To Check Out In Massachusetts
7. Lowell Winterfest
Taking place in mid-February every season, the Lowell Winterfest is one of the best festivals in Massachusetts to attend. With a soup competition where you can vote on your favorites from local restaurants, live music, an arts and crafts marketplace, lots of food vendors, and very cool entertainment, this one really has something for everyone.
8. Winterfest In Newton
The end of January brings the very fun Newton Winterfest, which is perfect for those in the greater Boston area. Featuring live ice sculpting demonstrations and impressive ice sculptures, the festival definitely feels like a true winter wonderland.
You’ll also find winter walks with hot chocolate and cookies, winter pop-up markets, live music and entertainment, food vendors, and costumed characters for the kids.
9. So Sweet Chocolate & Ice Sculpture Festival In Salem
One of the most unique winter festivals in Massachusetts is definitely the So Sweet Chocolate & Ice Sculpture event in Salem. In mid-February, this event brings a big kick-off fundraising party, sampling delicious chocolate, and beautiful ice sculptures together for one memorable winter weekend.
Salem is actually a fantastic place for anything chocolate related, too, as it’s home to some really great chocolate and candy shops: Ye Olde Pepper Co., which is the country’s oldest candy store, and Harbor Sweets.
10. Winterfest In North Adams
Up in The Berkshires, the North Adams Winterfest is one to have on your radar. Featuring horse drawn carriage rides around the park, chowder cook-offs, a bonfire, artisan markets and more, this is the perfect way to round out your getaway to the area.
11. Northampton Ice Art Festival
Northampton is a wonderful city in Massachusetts to visit, and in the winter, you can watch ice artisans create amazing sculptures during the Ice Art Festival. Typically taking place in January, you can follow along on a map and watch each artist take a block of ice, and turn it into something beautiful.
Can’t make it to the actual event? No worries! The sculptures stay on display until they melt, so you’ll have some time to see them all in person.
Best Things To Do In Massachusetts In Winter
12. Enjoy All The Christmas Festivities, Of Course!
I mean, this is a given, right? While winter doesn’t technically start until just a few days before Christmas, all the holiday festivities are in full swing right after Thanksgiving, and usually, the weather feels wintery the whole month of December.
So many places in Massachusetts have amazing Christmas celebrations that it’s actually hard to not find something to participate in during the entire month. But just in case, here are some of my favorites:
- Festivities on Cape Cod, including Chatham’s holiday celebration, and the holiday market in Provincetown.
- Nantucket’s Christmas Stroll
- Christmas in Edgartown on Martha’s Vineyard
- Christmas by Candlelight at Old Sturbridge Village
- Taunton’s Lights On Festival
- Christmas in Newburyport
- Winter Lights on Cape Ann
- City of Lights Parade in Lowell
- Stockbridge Main Street at Christmas
Boston also has some really cool Hanukkah celebrations to check out, including the Maccabee pop-up Hanukkah bar that features special cocktails, dreidel games, and food. Also check out the special Chanukkah Wonderland event at the Revere Boston Common hotel.
13. Hop Aboard The Hot Cocoa Cruise In Boston
One of the most fun things to do during the month of December in Boston is the hot cocoa cruise around the harbor. Offered only during the holiday season, this special cruise invites guests onto a 1920s vintage yacht while a live jazz band plays Christmas carols. Oh, and did I mention that hot chocolate is included? 😉
14. Plan A Special New Year’s Celebration
Much like the holidays, there’s tons to do for New Year’s around New England, too, including special events at fancy hotels, cozy cabin getaways, and fun parties.
Boston is especially perfect to plan a New Year’s celebration, and you can find parties all over the city, including at Harpoon Brewery, The Point’s party, and Hopster’s Brewery in Seaport.
There are also some really great New Year’s day lunch cruises offered around the harbor in Boston, which is a great way to kick off the very first day of the year.
The Chatham Bars Inn on Cape Cod offers a fun New Year’s party, followed by brunch the next day, and the Nantucket Hotel & Resort puts on a fabulous New Year’s Eve gala, with an option for a more low-key dinner, too.
Looking for something more casual? I love to recommend booking a cozy cabin in a place like The Berkshires, where you can watch your favorite movies by a fire, and ring in the New Year in a more peaceful way.
15. Tour All The Breweries
Massachusetts is home to some absolutely top-notch breweries, one of which is definitely in my top 3 in New England. I find the winter season is such a great time to sip on local brews, and really explore the brewery scene a bit more.
My favorite brewery in Massachusetts, and definitely in my top 3 in the region, is Tree House Brewing. Their Charlton location is perfect on a winter afternoon, and their covered outdoor pavilion even has cozy fire pits to enjoy that create the perfect vibe in the winter season.
Winter Hill Brewing is also a great place to check out in Somerville – and not just because of the name! It’s a combined small-batch brewery and coffee shop, so there’s all kinds of cozy to be had during your visit.
But there are so many wonderful breweries all over the state to check out, and if you’re looking for a way to beat that cold wintery weather, touring some of the local breweries is sure to warm you right up. Just please drink responsibly!
16. Hit The Slopes
In any destination that experiences a winter season, skiing is one of the most popular ways to get outside this time of the year, and Massachusetts is no exception.
I already touched on the great ski resorts in The Berkshires: Jiminy Peak, Ski Butternut, and Berkshire East. But there are some more awesome places to check out around the state, including Wachusett Mountain, Nashoba Valley, and Otis Ridge.
17. Make Your Own Winter Candle In Rockport
I mentioned Rockport earlier in this post as one of the best places to see while visiting the North Shore, and they also have a very cool workshop experience that’s absolutely perfect in the winter season. The Rockport Candle Company offers very fun make your own candle workshops. And I mean, who doesn’t love to light candles in the winter? It’s definitely one of my own personal favorite parts about this season.
During the workshop, you’ll pick out your very own custom scent and infuse it into your candle to take home with you as the perfect compliment to this cozy time of the year. While there, I also suggest looking around the adorable shop, as they have so many pre-made candles and scents that are to die for. I pretty much always have a Rockport candle burning during the holidays and winter season in my home.
18. Tour An Incredible Museum
Massachusetts is filled with incredible museums, and if you need to escape the cold in the winter season, this is the perfect opportunity to explore more of the arts, culture, and history in the state.
I already mentioned MASSMoCA and the Norman Rockwell Museum in the Berkshires, but here are a few more to have on your radar:
- Isabella Stewart Gardner Museum in Boston
- Peabody Essex Museum in Salem
- The Whaling Museum on Nantucket
- Museum of Fine Arts in Boston
- Boston Children’s Museum
- Harvard Art Museums in Cambridge
- Clark Art Institute in Williamstown
19. Book A Romantic (Or Relaxing Solo!) Spa Weekend
I love a good spa day after the busy holiday season has come to an end, and there’s something really restorative about booking a relaxing or romantic getaway during a quiet time of the year like January. There are so many cozy places to stay around New England that make for a romantic getaway or perfect spa weekend, and here are some ideas to check out:
❄︎ Mirbeau Inn & Spa in Plymouth: I know I mentioned them already, but the fireplaces in each room, combined with the extensive on-site spa make this very worth your while!
❄︎ Chatham Bars Inn on Cape Cod: Perfect for a romantic coastal getaway, with on-site dining and a spa.
❄︎ Beauport Gloucester: Another wonderful coastal option with on-site dining and luxurious accommodations.
20. Go Ice Skating
One of my personal favorite outdoor activities in the winter season is ice skating, and while I’m terrible at it, it’s always so fun to do. And there are some awesome places to spend the afternoon or evening ice skating around Massachusetts. Here are few places I recommend checking out:
- The outdoor rink at MarketStreet in Lynnfield
- The outdoor rink at Canterbury Farm (weather permitting, as long as the pond is frozen enough!)
- The outdoor rink at Frog Pond in Boston Common
- The Jack Kirrane Skating Rink in Brookline
- The Worcester Oval in Worcester
21. Explore A State Park After A Snow Fall
Massachusetts is filled with so many amazing state parks, and many of them are magical in the winter, especially after a snowfall.
I really love to wander around Maudslay State Park in Newburyport in the winter. It offers 16 miles of trails through fields, woods and scenic overlooks, and while they may not all be accessible after a big snowfall, it’s pretty easy to get around in the winter. They also offer groomed cross-country ski trails here, too!
But of course, there are tons of state parks all over to explore, and I encourage you to experience their natural beauty during this quiet time of the year.
22. Visit The Antique Shops
Home to lots of wonderful antique shops, this is a great way to spend a wintery afternoon in Massachusetts! I love to hunt down treasures for my home, and with many people starting fresh for the New Year and donating or selling items, I typically find lots of options in stores during the winter season.
And with Brimfield being home to one of the biggest antique shows in the entire country, you know you’re in the right place to find some great pieces.
Some great antique shops to check out in Massachusetts are:
- Sturbridge Antique Shops
- Brimfield Antiques Center
- Thoreauly Antiques in Concord
- Oldie’s in Newburyport
- Canal Street Antique Mall in Lawrence
23. Stay At A Cozy Inn
Nothing quite beats booking a New England getaway at a cozy and quaint little inn – many of which are historic, too! And Massachusetts is home to some of my absolute favorite places for a cozy inn getaway. The winter season can often bring off-season prices, depending on the location, and a more calm atmosphere, which is a big plus.
A few of my favorite cozy places to stay in Massachusetts are:
❄︎ Red Lion Inn in Stockbridge: A Classic New England style inn right on Main Street, with a lovely on-site restaurant.
❄︎ Harbor Light Inn in Marblehead: Already mentioned, but truly one of my favorite cozy inns to escape to in both the fall and winter – their quaint tavern is such a special place to hang out!
❄︎ Chambery Inn in Lee: A very homey New England style inn with options to add on in-room couples massages.
24. Visit The State’s Gorgeous Lighthouses
While many people picture a coastal lighthouse road trip for the summer, and even fall season, I honestly love them year-round. Yes, even in the winter! And Massachusetts has some beautiful lighthouses to see. In the winter, there’s a good chance you’ll have them all to yourself, too, which makes it even more fun.
A few of my favorites to visit are:
- Race Point in Provincetown
- Nobska in Falmouth
- Nauset Light in Eastham (especially pretty after a snowfall!)
- Scituate Light in Scituate
- Eastern Point in Gloucester
- Winter Island in Salem (such a perfect name!)
25. Spend The Day Snow Tubing
Many of the ski resorts in Massachusetts also have really fun snow tubing parks, and honestly, I love doing this in the winter. While I also enjoy downhill skiing, there’s something really stress-free about snow tubing that really puts you in touch with your inner child.
Here are some great snow tubing parks to check out this winter season:
- Butternut Ski Area
- Nashoba Valley
- Berkshire East
- Wachusett Mountain
26. Ski, Snowshoe, & Skate At Canterbury Farm
Canterbury Farm is such a great place for an outdoors day of fun in the winter season, and while many of these activities have already been mentioned, I wanted to give this farm its own section because it really deserves it.
They offer downhill and cross-country ski trails, as well as a charming little outdoor ice skating rink (open weather permitting). Additionally, they have all the rental gear you could need, including ice skates, as well as a small little lodge with hot drinks and light food options. They can arrange arrange ski lessons!
The grounds here are really nice and relaxing, and trails are groomed daily, and are well-marked and maintained. This is a really special place for winter outdoor fun.
27. Book A Wintery Sleigh Ride
One of the most romantic and memorable ways to celebrate winter is with a sleigh ride, and Cornerstone Ranch in Princeton is the perfect place to book this experience. Not only can you make your reservation online, they only offer private group rides, so you’ll have the entire wagon all to yourself.
Princeton is just about an hour or so from Boston, making the location easy to get to. They also invite you to stay a while after your ride to enjoy hot chocolate and s’mores by a campfire.
28. Find Your Favorite Cup Of Hot Chocolate
I don’t know about you, but I love a good hot chocolate in the winter, and Massachusetts is filled with places serving up a pretty great cup of this perfect wintertime treat.
As already mentioned, Chococoa Baking Co. in Newburyport is one of my favorites, and they do a great job offering different takes on hot chocolate throughout the season. Pair it with one of their whoopie pies for the perfect afternoon treat!
L.A. Burdick is a fantastic option for a cup of cocoa in Boston, and the 1369 Coffee House in Cambridge makes a really great Mexican hot chocolate for something a bit different.
But the best way to find your favorite, though? Just get out there and try them all!
29. Experience Dining In An Igloo
I think one of the most creative things to come out of the pandemic was all the different options for outdoor dining, and I’m so glad that igloo dining in the winter season continues to stick around. All over Massachusetts in the chilly months, more and more places are offering heated igloo outdoor dining experiences, and I’m here for it.
Here are some fun places to check out for igloo dining:
- Ocean Edge Resort Frost Bar in Brewster (they also make some really great winter cocktails!)
- Lock50 in Worcester
- The Tipsy Toboggan in Fall River
- Rye Tavern in Plymouth
- Mile Marker One in Gloucester
- 75 on Liberty Wharf in Boston
30. See If You Can Spot A Snowy Owl
Lastly on my list, I recommend a day to connect with nature, and try your luck at spotting a snowy owl. Massachusetts is actually known for being a home to the snowy owl in the winter season, and while they can be hard to spot, it can be done!
They tend to start to migrate to Massachusetts in late November, or early December, and stick around through March or early April, once the temperatures begin to rise again. So the winter months are truly the best time to spot them.
Some great places to spot the snowy owl in Massachusetts are:
- Salisbury Beach
- Parker River Wildlife Refuge
- Cape Cod & Nantucket Beaches (specifically the Atlantic coastline for Cape Cod)
- Crane Beach
- Duxbury Beach
- East Beach (New Bedford)
When looking for these beautiful birds, you’ll definitely want to have some binoculars, as you’ll usually spot them from a distance. And really, the only way to see them is to head out to the places mentioned above, and keep your eye peeled. I haven’t had the pleasure of spotting a snowy owl on my winter adventures in Massachusetts yet, but it’s definitely on my bucket list, and I try every time I’m in the area.
Note: It’s so important to be respectful of wildlife, so when looking for snowy owls, be sure to maintain your distance, don’t approach them, and allow them to be as they are in their habitat.
More posts you may enjoy:
- Christmas On Cape Cod: Lots Of Festive Ideas On What To Do!
- Magical Places To See Christmas Lights In Massachusetts
- Visiting Nantucket In The Winter
- The BEST New England Winter Getaways To Plan This Year
That’s A Wrap On Massachusetts In The Winter
Now that you’ve got the inside scoop on all the best things to do in Massachusetts in the winter, you’re ready to have your best season yet – or plan the perfect wintery escape! Whether you’re after a fun city adventure in Boston, or are hoping to enjoy the quiet coastline, there’s really no bad place to go in the state during this very festive time of the year. Happy Winter!