10 Ideas for a Festive Christmas in Massachusetts

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Snow covered path and wintery trees leading to a statue of a man on a horse and overlooking the city at dusk.

When it comes to festive holiday magic, Christmas in Massachusetts is hard to beat! With storybook towns that seem to be straight out of a Hallmark movie and grand Christmas celebrations that are all that is Merry & Bright, the Bay State delivers big when it comes to holiday fun.

If you’re looking for ideas for where to go and what to do for a festive Christmas in Massachusetts, you’re in the right place!

Quick Tip for Visiting Massachusetts in Winter

There’s a Scandinavian saying that gets tossed around New England each winter: “There’s no such thing as bad weather, only bad clothes.” Depending on where you’re from and what you’re used to, you might find Massachusetts’ winter weather to be a bit brutal!

An easy way to be prepared is to dress in layers so you’re prepared for bitter wind chill but can easily take off a layer or two if you find the weather is not as cold as you’d expected.

Don’t forget about footwear, either; canvas tennis shoes will get wet easily in slushy snow, and wet feet + cold weather does not equal a good time! Dress the part and you’ll have a blast during your Christmas in Massachusetts!

Head to The City on a Hill

City at dusk with many white lights, including an overhang with white lights in the foreground

Boston is a great getaway destination any time of year (have you been to Boston in the fall? Gorgeous!), but a trip to Boston in the winter is absolutely wonderful! Whether you have only a weekend or are planning an all-out romantic getaway, there are so many amazing things to see and do in Boston always.

And come the holiday season? Christmas time in Boston is absolute Christmas magic! There’s nothing quite like seeing the cobblestone streets and historic buildings adorned with twinkle lights and Christmas greenery; whether you’re visiting the museums, eating out, or grabbing a quick cup of joe, it seems like the entire city is transformed into a festive holiday paradise.

From ice skating at the iconic Frog Pond to the Faneuil Hall Tree Lighting, Boston is a magical Christmas vacation destination. Plus, there are so many amazing hotels and vacation rentals to choose from, you’ll have no problem finding the comfiest, coziest, most festive place to call home during your Christmas getaway!

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Take to the Cape

Cape Cod isn’t just a wonderful warm-weather destination, it’s also an amazing Christmas vacation spot! Cape Cod has so many adorable towns that are full of coastal charm; add in some Christmas spice and twinkle lights, and you’ve got the perfect recipe for Christmas magic! Head to Provincetown to see the Lobster Pot Christmas Tree, then schedule your ride on The Polar Express, departing from Buzzards Bay.

You’ll also find unique Christmas celebrations like the Cultural Center of Cape Cod’s annual Holiday Showcase, where historic displays are artfully decorated in all of the Christmas fripperies you can possibly imagine, and the Falmouth Holidays-By-The-Sea weekend with caroling and parades by the Nobska Lighthouse before Santa arrives in Falmouth Harbor by boat!

All around the Cape, you’ll find holiday strolls, artist’s markets, festive fun runs, enchanting villages, and so much more, so really, the Christmas magic is all around you on the Cape! With no shortage of great things to do on the Cape (and fabulous places to stay!) Cape Cod is a wonderful winter getaway destination for anyone looking for that perfect Christmas getaway spot.

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Step into a Norman Rockwell Christmas

A man and woman riding in a sleigh pulled by 2 Clydesdale horses in the snow

Editorial credit: James Kirkikis / Shutterstock.com

The Main Street of Stockbridge, MA is the Main Street depicted in Norman Rockwell’s “Home for Christmas (Stockbridge Main Street at Christmas)” work, and the first weekend of December, Stockbridge celebrates its role with their annual Main Street at Christmas celebration.

Stockbridge is already one of the most charming small towns in all of New England, but add in the vintage cars parked along the meticulously decorated Main Street with carolers singing in front of freshly-hung wreaths, and Santa overseeing it all in a horse-drawn carriage, and it’s about as picturesque as a Christmas vignette can be!

Don’t forget to visit the Norman Rockwell Museum while you’re in Stockbridge, and when it comes to where to stay, there are many great local options for comfy, cozy, Christmas accommodations. For a classic New England inn option, check out The Red Lion Inn. Not only is the inn a charming delight, but their onsite tavern and dining room make finding quality holiday meals a breeze!

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Go on Island Time in Nantucket

We all know Nantucket is a stellar summer vacation spot, but just because the winter winds have blown in doesn’t mean that Nantucket stops shining! If you are looking for Christmas magic in Massachusetts, it’s just a ferry or plane ride away; in fact, Vogue even calls December “Secretly the Best Time to Visit Nantucket,” so if Vogue says so…

Arrive in time for Nantucket’s Christmas Stroll on the first weekend of December where hundreds of decorated trees adorn Nantucket’s adorable downtown, and one lucky local artist is chosen each year to decorate the main 20-foot tree that stands at the top of Main Street and “talks.” Throughout the weekend, expect costumed carolers, craft shows, performances, tours, and more! Be sure to visit the Nantucket Whaling Museum for their eagerly awaited annual Festival of Trees, too.

The island is a glittering holiday wonderland of twinkle lights, so most anywhere you choose to stay will likely be decorated to the nines with all the sparkling baubles and fresh-cut greens that a person could want. In addition to being home to one of the best hotels in New England (The Wauwinet), Nantucket also has lots of great vacation rentals  and other gorgeous hotels to choose from, too, so wherever you stay will be the perfect fit for your holiday getaway!

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Unwind in the Berkshires

White picket fence with green holiday garden and white lights with big red bow

Looking for a beautiful Christmas landscape? Check out the Berkshires, where you can get all the holiday joy of the season without the hustle and bustle of some of the bigger cities. Go on a Holiday House tour at Edith Wharton’s The Mount in lovely Lenox, then on to a Holiday Lights tour at Herman Melville’s Arrowhead in nearby Pittsfield to get a feel for the spirit of Christmases past!

Visit a few of North Adams’ great museums to take in some local art and history; North Adams has a lot to do and see! Catch a holiday show or two with the Berkshire Theatre Group on your way to and from the sweet holiday markets and adorable, fully-decorated downtowns as you finish your Christmas shopping in the Berkshires.

There are a lot of amazing vacation rentals to choose from all around the Berkshires, but if you’re looking for a little luxurious pampering during your Christmas vacation, check out Blantyre in Lenox. This gorgeous castle-esque Gilded Age era hotel and spa has every amenity a person could want, including phenomenal dining at the onsite restaurant. Luxury or not, you’re sure to find the perfect spot for you and yours during your Berkshires Christmas vacation!

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Have a Christmas Ski Adventure

Massachusetts may not be as well-known as some of New England’s more dramatic ski destinations, but you can find some great skiing, snowboarding, and snow tubing in the Bay State! Check out Ski Butternut in Great Barrington, where you’ll find 100 skiable acres and 100% snowmaking capabilities; Butternut typically opens the third week of December, so you’d be arriving in the beautiful Berkshires at the perfect time to enjoy all the magnificent holiday decorations.

Most of Massachusetts’ ski spots are in or near the Berkshires with one notable exception: Blue Hills Ski Area in Canton, just outside of Boston. Not only does Blue Hills have 60 skiable acres and 90% snowmaking coverage, but this modest ski area is only 10 minutes outside of Boston, so you can enjoy all that wonderful Christmas in Boston magic during your ski-cation!

There are some great vacation rentals available throughout the state to choose from, too. For a fantastically fun and action-packed Christmas getaway, hit the slopes during your Massachusetts holiday vacation!

Visit a Christmas Tree Farm

A woman in a winter hat sniffing pine tree branches

Depending on where you’re visiting from, you may not be interested—or able—to buy your own Christmas tree during your Massachusetts vacation, but there are so many amazing Christmas tree farms in Massachusetts where you can go and enjoy the experience of hands-on, small-town Christmas festivities!

For example, Smolak Farms in Andover has a drool-worthy Candy Bar to satisfy your sweet tooth with, and Wine & Wreath Making, Cookie Decorating, and Gingerbread House workshops. Sleighbell Farm in Sutton offers a neat prop area to take your own holiday photos in, with fun, festive props like a giant holiday wreath and an antique sleigh!

Most Christmas Tree farms in Massachusetts have great gift shops with unique, one-of-a-kind finds that would make for the perfect souvenir or Christmas gift, and many offer holiday treats like hot cider, hot chocolate, or fresh-baked cookies to their visitors. If you’re looking for a sweet and simple Christmas activity during your Christmas getaway, a visit to the nearest Christmas tree farm may be just what you’re looking for!

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Be Charmed by Cape Ann

Cape Ann’s charming North Shore towns only become even more picturesque as the holiday decorations go up, turning the Cape’s storybook streets into what looks like scenes from a Christmas card!

Some notable Cape Ann Christmas happenings include Santa arriving by lobster boat in Rockport before the tree lighting ceremony, the Middle Street Walk and Gingerbread House contest in Gloucester, the Manchester Holiday Stroll in Manchester, and the Cape-wide Winter Lights map that will lead you to the most spectacular Christmas lights on the Cape!

There are so many great things to do and see in Rockport, Gloucester, and elsewhere around Cape Ann, but if you’re looking for the perfect place to cozy up during your holiday getaway, consider a stay at one of Rockport’s great hotels. If it’s romance you’re after, check out Addison Choate, one of the best spots for a romantic Massachusetts getaway. Wherever you choose to stay during your Cape Ann Christmas getaway, you’ll find plenty of that classic Cape Ann charm!

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Revel in Christmas Magic at Martha’s Vineyard

2 white candles in front with a background of snow and trees with white lights at dusk

A beautifully kept, idyllic vacation spot any time of year, come Christmas, Martha’s Vineyard becomes a pristine example of holiday charm! Take in the Christmas in Edgartown Parade on the second weekend of December and enjoy the Lighting of the Edgartown Lighthouse ceremony, the classic Dickensian Christmas Carolers, horse-drawn carriage rides around the harbor, and more.

Not only will the halls be decked with all of the twinkle lights and fresh evergreens you can imagine, but there is even a snow machine that runs on weekend evenings to ensure that the Christmas scene is set to be just as picturesque as picturesque can be! What better way to bring a little extra Christmas magic to your boutique shopping?

Ocean Park Lights in Oak Bluff is an absolute sight to see while you’re enjoying all the great things to see and do on Martha’s Vineyard, as this already delightful park becomes a winter wonderland of light and festive holiday decorations. With great options for where to rest your head during your Christmas vacation on Martha’s Vineyard, you’re sure to have a holly, jolly time wherever you choose!

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Nestle in Newburyport for this Season’s Greetings

One of the best beach towns in the Bay State, Newburyport isn’t just a fair-weather vacation destination! Not only is there plenty to see and do outside of the holiday season, but Christmas brings all sorts of fun festivities to the area to really take your holiday getaway up a notch.

On the first Sunday after Thanksgiving, Santa arrives in Newburyport by boat, and then it’s on to the Christmas parade! Cheer Santa on before the tree lighting ceremony, where carols are sung “loud for all to hear,” because everyone (especially Buddy the Elf) knows that’s the best way to spread Christmas cheer!

Shop Newburyport’s lovely downtown during Holiday Invitation Nights, when live entertainment, refreshments, and plenty of twinkle lights make downtown holiday shopping just a little more Merry and Bright! There are several great options for where to stay while in Newburyport, but Essex Street Inn is a gorgeous historic inn that places you in perfect proximity to all the downtown holiday festivities. Christmas in Newburyport is a slice of coastal, small-town heaven!

There are so many festive ways to spend Christmas in Massachusetts; whether you’re looking for big-city Christmas magic or small-town sweetness during your holiday getaway, you’ll find it in the Bay State!

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