10 Magical Things To Do In Massachusetts During the Holiday Season

Get your tree decorations and holiday lights out and grab a hot cocoa — it’s Christmas time! As winter descends and the festive season begins, you may be wondering what the best things to do in Massachusetts are at this time of year.

At Keolis massAdventures, we’re just as excited about the holiday season as you, which is why we have a range of holiday-themed Day Trips Near Boston available! To help you decide on what festive activity is best for you, we’ve created this blog about the 10 magical Christmas things to do in Massachusetts. 

So strap on your boots and grab a beanie, because even though it’s cold outside, adventure awaits!

a mother with a boy and girl infront of Christmas lights

Source: Stevens-Coolidge House & Gardens

Enjoy Christmas by Candlelight at Old Sturbridge Village

Step back in time for a Christmas like no other at Old Sturbridge Village! The village, which recreates a 19th-century New England town, brings festive traditions of yore to life. Discover the stories behind Christmas stockings and tree ornaments, meet Santa in his own cabin, and listen to a performance of carols. 

Even if you don’t visit Old Sturbridge Village at Christmas, make sure you include it on your bucket list, as it’s one of our Top Attractions and Hidden Gems in Central MA!

Experience a Colorful Christmas at Castle Hill 

At Christmas, Castle Hill on the Crane Estate turns into a festive spectacle. Each year, the mansion is beautifully decorated, which you can experience as part of our winter Guided Tour of Castle Hill on the Crane Estate. Inside you’ll find each room decorated in a different vibrant color scheme. You’ll also get to drink hot chocolate, play games, and browse the gift shop. 

Winter Castle Hills exterior covered in snow

Visit the Enchanted Village

Since the 1960s and 70s, Jordan’s Enchanted Village has been a staple of the Massachusetts festive season. From its beginnings in Boston, it’s now held in Jordan’s store in Avon, just a one-hour train drive from its original location. Stroll among figurines, go sliding down the tube, skate on the enchanted ice, and be amazed by a laser light show. And don’t miss their delicious signature blueberry muffins!

Join Deck the Halls at Hammond Castle

For some luxurious festivities, Hammond Castle transforms into an opulent Christmas display over November and December. Adorned with rich colors and whimsical decor, the museum truly brings the magic to life. See this historic Massachusetts attraction become a hub of celebration as part of our Hammond Castle Museum Tour, and admire how the castle is lit up in an otherworldly scene!

Hammond Castle interior holiday season

Go Ice Skating in Worcester

While New York City’s Rockefeller Center may be home to one of the most iconic ice skating rinks, the Oval Rink in Worcester is 4,000 square feet larger! Easily accessible by Communter Rail, it’s the perfect place in winter for the whole family to enjoy — you’ll likely find yourselves skating for hours! You can rent your skates at the rink, move to the music, and grab a bite to eat after working up a sweat. Head to the Mercantile Worcester for pizzas and cocktails or Chashu Ramen for Japanese cuisine!

Meet the Reindeer at Stone Zoo

Kids (and adults) won’t want to miss the opportunity to meet the reindeer of Stone Zoo! Every year, the zoo turns into a twinkling spectacle, allowing you to explore the enclosures of bears, lynxes, and more under the night sky! A major highlight is the opportunity to have hot chocolate with the resident reindeer, Holly and Aoife. Take your choice of topping and get to know Santa’s helpers!

Admire the Winterlights at Trustees Properties

Witness hundreds of lights illuminate three garden properties of the Trustees: Naumkeag in Stockbridge, Stevens-Coolidge House & Gardens in North Andover, and Eleanor Cabot Bradley Estate in Canton. Every year over the festive season, these historic estates transform into a breathtaking spectacle with music and food. Winterlights has even been voted as one of the best holiday light shows by the USA Today! Canton and North Andover are easily accessible by Commuter Rail, making Winterlights an unmissable holiday excursion.

Eleanor Cabot Bradley Estate holiday lights

Source: Eleanor Cabot Bradley Estate

Feel the Magic of the Season Aboard the Polar Express 

Every year, The Polar Express makes its way down to Buzzards Bay spreading holiday cheer and bringing guests on a magical train ride to the North Pole. Perfect for families, this seasonal event will fill you with holiday cheer, hot chocolate, and don’t forget, cookies!

Enjoy a Sleigh Ride at Cornerstone Ranch 

For a classic Christmas experience, why not go on a sleigh ride? At the Cornerstone Ranch in Princeton, you can go dashing through the snow in a sleigh or carriage, driven by the ranch’s friendly horses. Whether you’re a family looking for something new this Christmas or a couple searching for a romantic and festive date, you’ll be jingling all the way!

Find Snowy Owls at Castle Crane Neck

While it may seem that no animals would be around during winter, there is one that comes out to play — the snowy owl. These beautiful birds spend their winters on the dunes of Castle Neck, where you have the chance to spot them as part of our Snowy Owl Dune Trek. During this four-mile hike through the Crane Wildlife Refuge, your guide will help you track these elusive birds while pointing out the unique flora.

Bring binoculars and make sure to dress warmly — this crisp adventure will be well worth it!

White owl in the snow

Discover More of Massachusetts 

Whatever the season, the state of Massachusetts has a host of incredible attractions, unbeatable experiences, and outdoor adventures. Better yet, they’re all easily accessible by train! That’s why Keolis massAdventures harnesses the Commuter Rail system as part of our Day Trips from Boston, making MA accessible to local Bostonians and tourists alike. If you have any questions about our tours, please don’t hesitate to get in touch

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