Best Holiday Events To Go To in the Boston Suburbs for Christmastime

Nov 25, 2022

We’ve made a list (and checked it twice!) of the best things to do and see in the Boston suburbs this holiday season.

The Boston suburbs are the place to be during the holidays. As you’re touring towns, be sure to add some of these tree lighting events, outdoor Christmas light displays and holiday performances and activities to your must-see list. 

North of Boston

December 1-23: A Christmas Carol—A Musical Ghost Story at North Shore Music Theatre (Beverly)

Watch as Ebeneezer Scrooge discovers the true spirit of the holiday season in this musical version of A Christmas Carol. Featuring classic songs like God Rest Ye Merry Gentlemen, Here We Come A-Wassailing, and We Wish You A Merry Christmas, this award-winning production — now in its 31st year — is a holiday tradition New Englanders look forward to all year long. Bring an unwrapped, unopened toy for Tiny Tim’s Toy Drive.

December 1-4: Marblehead Christmas Walk; December 10-11: Land of the Sweets — A Nutcracker Suite (Marblehead)

The seaside town of Marblehead knows how to make things merry all month long. The festivities kick off December 1-4 with the Marblehead Christmas Walk, a four-day-long extravaganza that includes a parade, tree lightings, concerts, and even a visit by the big guy himself. The following weekend (December 10-11) you can take in a performance of Land of the Sweets, a whimsical re-imagining of The Nutcracker, at the Marblehead Little Theater.  

December 1-4: 2nd Annual Winchester Stroll Weekend (Winchester)

Want to get into the holiday spirit in style? Show off your gingerbread house-decorating skills, join the “Troll on the Stroll” scavenger hunt, make an appearance at the Yule Ball at the local bookstore, shop at local boutiques, and experience all that downtown Winchester has to offer at the annual Winchester Stroll Weekend. PS – Don’t miss the Friday night tree lighting on the Town Commons.

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December 3: Arlington Heights Winter Window Painting (Arlington)

Arlington residents are painting the town for the holidays — literally! More than 55 storefront windows will be transformed with paintings of snowmen, polar bears, snowy play, and other wintry scenes. Grab a hot cocoa and stroll the downtown streets admiring the artists at work. Can’t make it December 3? Paintings will brighten the town through February.

December 2-3: Home for the Holidays (Melrose)

If you’re thinking of making yourself at home in Melrose, check out Home for the Holiday’s, a citywide holiday open house. This magical weekend kicks off on Friday night with holiday singing and a tree lighting, followed by Santa riding into town on a fire truck. The fun continues from 10am-2pm on Saturday with a packed schedule of events including a performance of “The Nutcracker.” Don’t miss a ride on the holiday trolley, which will be carrying shoppers throughout the charming downtown shopping district.

West of Boston

November 25-27; December 16-18: The Nutcracker (Weston)

The town of Weston has its very own ballet troupe — and the Commonwealth Ballet’s family-friendly production of “The Nutcracker” has become a holiday tradition for Boston-area families. Purchase tickets here.

November 27: Holiday Lighting on the Common (Natick)

Natick lights up the night Thanksgiving weekend. Stop by the Natick Commons for crafts, caroling, an antique car parade, and a holiday dance performance followed by the lighting of the town-wide holiday lights.

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December 3: Holiday Haybale Tree Lighting at Powisset Farm (Dover)

Dover locals get into the holiday spirit at Powisset Farm, a historical, 109-acre working farm where you can stroll through the Solstice StoryWalk, visit with the famed Powisset pigs, make a craft, warm up by a fire pit, and enjoy farm-fresh food, hot cider, hot toddies, hot chocolate or craft beer while you take in the magic of the beautiful holiday light display. The event is free but advanced registration is required; register here.

December 3: Hopkinton Holiday Stroll (Hopkinton)

How does Hopkinton holiday? Check it out at the Hopkinton Holiday Stroll, where you can work your way through your holiday gift list at charming shops and boutiques, take a ride on a horse-drawn carriage around the Commons, watch ice sculptors at work, then grab a bite to eat at a local restaurant before the annual tree lighting.

December 4 & December 11: Wellesley Holiday Strolls (Wellesley)

The town of Wellesley celebrates the holidays with not one but TWO holiday strolls. On December 4, visit the 60+ stores and restaurants in Wellesley Square, where you can take pictures with Santa, go on a sleigh ride, and so much more. The following weekend, head to Linden Square, Wellesley’s upscale shopping, dining, and lifestyle destination, to visit with Anna and Olaf from “Frozen,” check out the beautiful holiday decorations, watch a balloon artist at work, and sip on hot cocoa while you listen to the Wellesley High School carolers. 

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Had enough shopping? Take in the Festival of Trees at the Garden at Elm Bank, where dozens of decorated trees and a festive model railroad are on display through December 31. Buy tickets here.

December 10: Wayland Town Center’s Holiday Stroll and Tree Lighting (Wayland)

There is “snow” much fun to be had at Wayland Town Center’s annual holiday stroll and tree lighting. Stop by the face painting and coloring stations with the kids, snap pictures with Santa, sing (or listen to) some carols, and shop the holiday marketplace before wrapping up your day with the tree lighting on the green.

Northwest of Boston

November 27: Holiday Tree Lighting (Westford) 

Celebrate the holidays with a historical twist at the Westford Historical Society & Museum’s holiday tree lighting, where you’ll hear about the history of the tree lighting tradition and the origins of Denny’s Tree on Westford Common.

December 3: Photos With Santa (Westford)

If you’re on the “nice” list, you can also get your picture taken with Santa at WestfordCAT (Community Access Television) located at 487 Groton Road, on Saturday, December 3 from 11 am – 1 pm. Donations are appreciated and support free community media programs and services.

December 4: Concord Annual Tree Lighting & Holiday Parade (Concord)

It’s beginning to look a lot like the holidays in beautiful downtown Concord, where storefronts are all decked out for the holidays. Be there as Santa rides down Main Street on a fire truck to light the town tree.

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Southwest of Boston

November 18-December 31: Magic of Lights (Foxborough)

Forget the sugarplums — you’ll have visions of holiday lights dancing through your head after driving through this festive display created with nearly one million sparkling lights. Decorations include the 200-foot-long Tunnel of Lights, Candy Cane Lane, Toyland, 12 Days of Christmas, Prehistoric Christmas (complete with life-sized dinosaurs!), a Bigfoot Monster Truck, and a 32-foot-tall animated Barbie. Buy tickets in advance here.  

December 2: Dedham Holiday Stroll (Dedham)

Dedham decks the halls for the holidays with an antique working model train and Christmas village, festive storefronts, and an official tree lighting by Santa Claus himself. Afterwards, head to Dedham Community Theater for a visit and photos with Santa.

South of Boston

December 2: Christmas in the Square (Hingham)

Want to experience a picture-perfect New England holiday? For more than 40 years, downtown Hingham has hosted Christmas on the Square, a holly, jolly old-fashioned hometown celebration that attracts neighbors from across the South Shore. Don’t miss the screening of “It’s a Wonderful Life”!

December 3-5: Hometown Stroll (Plymouth)

Historic Plymouth keeps the cheer close to home with its annual Hometown Stroll. Check out festive storefront displays as you shop local boutiques for just-right gifts, be awed by the festival of trees, and maybe even win something in the “loving local giveaway.”

Multiple Locations

November 25-January 7: Winterlights (Canton, Stockbridge, and North Andover)

Imagine walking in a winter wonderland without even leaving the ‘burbs. Three Boston- area gardens run by The Trustees of Reservations are transformed into silver lanes aglow with thousands of shimmering holiday lights. Tickets sell out fast, so check the website for availability.

Wondering which Boston suburb you want to call home? Get in touch and our Boston-area Strategist will help you find the perfect fit.

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