A Toast to Holiday Joys in Massachusetts

Sponsored by the Massachusetts Office of Travel and Tourism

From seeing Santa on the seashore to raising a glass to peace and goodwill at a cozy craft brewpub, there are endless ways to get into the holiday spirit in Massachusetts. You can stroll Main Street for one-of-a-kind gifts, be dazzled by light shows, or enjoy a festive meal at a classic New England inn. Whether it’s a solo outing or a special event with family and friends, Massachusetts is filled with so many merry destinations for making the most of the holiday season, you’ll wish it lasted all year long.

1. Check out the festive scene at a historic inn or hotel.

At this time of year, inns and hotels across the Commonwealth are decking their halls (and check-in desks) as they invite guests and visitors alike to partake in seasonal treats. Among those celebrating the holiday spirit is the Inn at Hastings Park in Lexington, which hosts a Santa Tea at the inn’s Town Meeting Bistro on Dec. 14, 15, 21, and 22. All ages can enjoy a high tea service, sweet and savory bites, gingerbread decorating, crafts, and time with Santa Claus (plus holiday cocktails for the grownups). More of a morning person? The Publick House Historic Inn in Sturbridge offers Breakfast with Santa (Dec. 8, 15, and 21), featuring a full breakfast buffet and the chance to hit up St. Nick with any last-minute requests for Christmas delivery. 

With the museum village of Old Deerfield providing a suitably picturesque setting, the Deerfield Inn’s on-site restaurant, Champney’s Restaurant & Tavern, holds a Dinner with Santa & Mrs. Claus on Dec. 1-3, 9-10, and 16-17. The event boasts a full dinner menu (with the addition of Mrs. Claus’s cookies) and the chance to spend time with the North Pole’s most famous couple. Those wanting a more decadent dining experience can head to Cape Cod for the Christmas Grand Buffet on Christmas Day at Chatham Bars Inn, with harbor views, seafood displays, holiday roasts, and desserts galore. Back in Boston, the Dec. 25 Christmas Brunch at Boston Harbor Hotel’s Rowes Wharf Sea Grille is a luxe spread of baked ricotta crepes, dry-aged prime sirloin, raw-bar seafood, and more, all served with Boston Harbor as the backdrop.  

2. Hit the streets for some downtown revelry. 

If you’re looking to join a joyful crowd, downtown is the place to be. On Dec. 6-8, head to Provincetown for Holly Folly, the nation’s oldest and largest LGBTQ+ holiday celebration, where you can stroll the boutiques and galleries of Commercial Street, take in a drag show at Provincetown Town Hall, or hit up The Canteen’s Holiday Market (which runs every weekend from Nov. 29 to New Year’s) for everything from mulled wine to Christmas ornaments both naughty and nice. 

Boston’s SoWa Winter Festival is set to make its ninth annual rollout this year from Nov. 29 to Dec. 22. Pop into this holiday shopping extravaganza at the SoWa Power Station in the South End for a mix of vendors selling unique gifts for your friends, family, and four-legged companions. There are food trucks, too, as well as a bar and beer garden to keep you fueled for further retail adventures.

For a dose of holiday spirit on wheels, explore downtown Salem while enjoying “A Christmas Carol” aboard the Salem Trolley (Dec. 1-23), which brings Scrooge along for the ride as Charles Dickens’s classic tale is brought to life. 

3. Get your glow on at a seasonal light show.

The lights are shining bright at spectacular displays across the state this holiday season, such as Night Lights at the New England Botanic Garden at Tower Hill in Boylston. Running Nov. 23-Jan. 5, this year’s event is themed “Color Cascade” and also ushers in a new attraction: Guests can now skate under the stars at an outdoor skating rink. After taking a twirl and exploring the vibrant displays, guests can warm up by firepits with hot cocoa or hunt for gifts in the Garden Shop. 

A marquee event for The Trustees, Massachusetts’s largest preservation and conservation nonprofit, Winterlights runs Nov. 29-Jan. 4 at three of the group’s properties this holiday season: Naumkeag in Stockbridge, the Stevens-Coolidge House & Gardens in North Andover, and the Eleanor Cabot Bradley Estate in Canton. Each features thousands of shimmering lights as well as festive music, seasonal treats, and the chance to wander some gorgeous garden landscapes. 

Little ones won’t want to miss out on Zoolights, which runs through Jan. 5 at Stoneham’s Stone Zoo. A constellation of lights fills the tree-lined paths of the 26-acre zoo, and visitors can even stroll through a festively decorated Yukon Creek, home to the zoo’s black bears, Canadian lynx, and reindeer. (Be sure to check out the zoo’s website for Hot Chocolate with the Reindeer special events, too.) Southwick’s Zoo in Mendon has its own light-filled spectacular with Winter Wonderland, which runs through Dec. 29 and features more than 4 million lights and displays that turn the zoo into a land of enchantment. There’s a nightly holiday variety show as well as meet-and-greets with Santa, plus holiday shopping at the Purple Peacock Gift Shop. 

4. Blend holiday hops and shopping at a local brewpub. 

’Tis the season for multitasking, so why not enjoy the seasonal flavors of local craft brewers across Massachusetts while also getting in some gift shopping and holiday crafting? At the 2024 Holiday Market at Southwick’s Westfield River Brewing Co. on Dec. 8, guests can enjoy an afternoon of live music and food trucks with a side of local gift shopping, plus plenty of craft beers and cocktails to choose from. In Cambridge, meanwhile, Lamplighter Brewing Co. hosts a wreath-making workshop on Dec. 11 for those looking to DIY their holiday door decor. 

On Dec. 15, Notch Brewing’s Salem taproom hosts its annual German Holiday Market, showcasing one-of-a-kind finds from local artisans and makers alongside German sausages, leberkäse, and pretzels — a true taste of Bavaria on the North Shore. Also on Dec. 15, A Very Merry Market returns to Cape Cod Beer in Hyannis, affording the chance to sip an Old Man Winter ale while perusing the wares of vendors and makers throughout the taproom and warehouse. 

Closer to Boston, check out the annual Holiday Market at Trillium Brewing Co.’s Canton and Fort Point locations (Dec. 7 at Fort Point; Dec. 7-8 and 14-15 at Canton). Enjoy live music and local brews, and browse a lineup of handmade goods that is sure to make your gifts the favorites under the tree.

5. Enjoy all the festive feels along the waterfront.

While Santa Claus and his trusty reindeer might feel most at home in the sky, you can find festive reasons to head down to the sea during the holidays in Massachusetts. Enjoy lunch with Santa and soak in harbor views during a special two-hour Lunch with Santa voyage with Boston Harbor City Cruises Dec. 7 and 14, where kids can deliver their Christmas lists to St. Nick and pick up a goodie bag of their own. Boston Harbor City Cruises also operates a Christmas Eve Premier Brunch Cruise that delivers festive cocktails, live music, and a full brunch spread alongside views of the USS Constitution and the Boston waterfront. Classic Harbor Line offers a variety of holiday cruises on Boston Harbor, including a 1.5-hour sunset cruise whose “golden hour” light is perfect for taking that family holiday-card photo. Beyond Boston, Gloucester’s Beauport Cruiselines invites you to experience “Santa at Sea” on Dec. 15, when passengers can take pictures with the guest of honor, enjoy holiday tunes and treats, and take part in a toy drive. 

For those who like to stay on land but still enjoy the waterfront, a number of Massachusetts coastal towns have made a delightful tradition of welcoming Santa by boat during the holidays. On the morning of Dec. 7, for instance, Marblehead will cheer the arrival of the jolly old elf via lobster boat, a highlight of the town’s annual Christmas Walk. That same day in Scituate, Mr. and Mrs. Claus will come gliding in on the harbormaster’s boat and be on hand for photos on the harbormaster’s deck as part of Scituate’s Holidays in the Harbor fun.

For more Massachusetts holiday travel ideas, go to VisitMA.com.