Massachusetts Holiday Markets, Parades, and Celebrations in Central Mass & Boston
Updated November 20, 2025 | Published November 12, 2025 by Angela Talbot | Reading Time: 10 minutes
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The holiday season in Massachusetts is nothing short of magical, with festive events and traditions lighting up every corner of the state. From charming holiday markets brimming with unique gifts to dazzling tree lighting ceremonies and spirited parades, there’s something to spark joy for everyone. In this two-part guide, we’ll explore the best holiday happenings across the Central Massachusetts area and the bustling Boston region. Whether you’re looking to sip hot cocoa while browsing local crafts or marvel at twinkling lights and holiday cheer, these events are sure to make your season merry and bright. We did the research so you don’t have to. Let’s dive into the festivities!
Central Mass Holiday Celebrations
Douglas Common Holiday Tree Lighting
Saturday, November 29 at 4:30 p.m. | Douglas Common, 1 Common St, Douglas, MA
On the night the town of Douglas, Massachusetts lights up it’s Town Common, you can experience carolers, photos with Santa, refreshments, and holiday magic. At 5:15 p.m. Santa arrives in a Fire Truck, after which you can snap a photo with old St. Nick himself and the reindeer. At 5:45 p.m. the gazebo and trees will be lit! From 6:00-7:00 p.m. enjoy the festive tunes of Very Merry Dickens Carolers, all while hot chocolate and pastries are served at First Congregational Church across the street. Oh, and did we mention this whole event is free? Parking is available at the Highway Department (across the street from the Ice Cream Lady/Family Convenience Center) and a quick ride on the free shuttle bus will get you to the Common. Shuttle bus starts at 4:30 p.m. Handicapped parking is available on Common Street and behind the First Congregational Church. Find more information at the event link.
Northbridge Santa Parade and Tree Lighting Ceremony
Saturday, November 29 from 12:30 p.m. to 5:00 pm | Whitinsville Town Common, Whitinsville, MA
In Whitinsville, a village in Northbridge, MA, they will be holding their annual Santa parade and tree lighting ceremony on November 29. The parade route begins at that Northbridge Fire Department at 1681 Providence Road Santa and Mrs. Claus ride a fire truck all through town, ending at the Whitinsville Town Common where the tree lighting ceremony will be held from 3:00 p.m. to 5:00 p.m. Join in on this festive fun. You can even track Santa’s firetruck at the event link above.
Fitchburg Holiday Tree Lighting Ceremony
Sunday, November 30 at 5:30 p.m. | Historic Upper Common, 914 Main St, Fitchburg, MA
Fitchburg Civic Days hosts the city’s annual tree lighting ceremony featuring local businesses, caroling, hot chocolate, s’mores, a holiday lights car show, and special guests. This event is also free to attend.
Webster Christmas Tree Lighting
Thursday, December 4 at 5:00 p.m. | Webster Town Hall Lawn, 350 Main St, Webster, MA
At the Webster Town Hall, kick off the holiday season at this Christmas Tree lighting which includes hot chocolate, a meet and greet with Santa and Mrs. Claus, and live music. The tree lighting is immediately followed by a Christmas Concert at the Gladys E. Kelly Public Library (2 Lake St) at 6:30 p.m.
Worcester Festival of Lights
Friday, December 5 | Worcester Common, 455 Main Street, Downtown Worcester, MA
The Worcester Festival of lights is one of the city’s biggest holiday events. The lighting this year will feature several illuminated art installations by local artists that will be on display on the Common until March 1, 2026. The Festival of Lights features a tree lighting, food vendors, musical performances, a visit from Santa, carriage rides, ice skating (skate rentals available), and more. The Worcester Public Library is also open with a hot cocoa station, giveaways, and other fun family activities.
Uxbridge First Night
Saturday, December 6 | North Main Street, Uxbridge, MA
On the first Saturday night in December for 28 years, the town of Uxbridge, MA becomes a magical festive wonderland. Businesses down North Main Street and beyond open their doors for a holiday stroll while vendors set up shop on the town common. The main event, however, is the holiday parade, featuring floats from locals and 3 different high school marching bands. This year, the parade concludes with a fireworks display. It’s a fantastic free event for the whole family.
Sutton Chain of Lights
Saturday, December 6 from 10:00 a.m to 6:00 p.m. | Sutton High School, Sutton, MA
The Sutton Chain of Lights takes place all over town, with a hub at Sutton High School. There, you can hop on a trolley to explore 3 different routes. All three routes make stops at a handful of local business all over town where you’ll find free samples, sweet treats, photo ops, and other entertainment. The trolleys run from 10:00 a.m. to 4:00 p.m.. At 5:00 p.m. the town returns to the High School for performances plus Santa and the tree lighting on the town common.
Oxford Holiday Extravaganza
Saturday, December 6 from 10:00 a.m. to 3:00 p.m. | Oxford High School, 495 Main St, Oxford, MA
The Oxford High School Student Council hosts this vendor fair in the high school cafeteria where you can shop for homemade gifts from 70 vendors. Support local businesses this holiday season and enjoy a hot breakfast ($5 per person) with photos with Santa. Try your luck at winning several raffles that will be set up. Raffle tickets are $1 per ticket. Raffles and breakfast are cash only.
Kelley Square Tree Lighting Extravaganza & Holiday Stroll
Saturday, December 6 from 3:00 p.m. to 5:15 p.m. | Kelley Square/Canal District, Worcester, MA
This event at the Worcester Public Market and surrounding businesses is jam packed with winter magic. It not only includes a tree lighting in Kelley Square, it also features a meet & greet with Santa and Mrs. Claus, horse drawn wagon rides, antique firetruck rides, samples from Table Talk Pies, Polar Beverages, Jersey Mike’s, and many local more businesses. WXLO will providing music and giveaways. Plus, photo ops with Rudolph, Frosty, The Grinch, Mickey Mouse, Goofy, Santa’s Elves, and all your local sports mascots – from the WooSox, Pirates, Bravehearts, and Railers! Stick around after the tree lighting for an official after party: Location to be announced.
Shrewsbury Winter Festival featuring Yuletide Market and Light on the Common
Saturday, December 6 from 3:00 p.m. to 7:00 p.m. | Shrewsbury Town Common, 584 Main St, Shrewsbury, MA
This 6th annual Winter Festival in the town of Shrewsbury grows larger every year. This year’s celebrations features a Yuletide Market with dozens of local craft vendors offering holiday gifts, handmade crafts, art, jewelry, gourmet treats, and more. Live entertainment from carolers, bands, and dancers can be enjoyed all throughout the evening. Satisfy your appetite with a Festive Food Court with local food trucks and a fireside beverage lounge with beer and wine. Drop the kids off at the Kid Zone where they can enjoy carnival games, a photo booth, and more fun activities. All leading up to the tree lighting on the common at the end of the night.
Spencer Light Parade
Saturday, December 6 at 7:00 p.m. | Main Street/Old Main Street, Spencer, MA
The Spencer Light Parade is an annual holiday tradition in the town of Spencer where locals dress their cars and floats up in as many lights and decorations as possible. Anyone can participate, whether a local business or just a resident of the town. It’s a bright sight to see!
Webster First at the 2024 Spencer Light Parade via Spencer Cable Access
Millbury Chain of Lights
Sunday, December 7 10:30 a.m. to 4:30 p.m. | Millbury, MA
The town of Millbury has its own Chain of Lights with festive activities going on all around the town. The hub of activity is at the Asa Waters Mansion where the tree lighting will take place at the end of the night. Hop on a trolley to get to more than 40 businesses that are participating in the events with great food and entertainment throughout the day.
White Christmas in West Brookfield
Sunday, December 7 from 10:00 a.m. to 4:00 p.m. | West Brookfield, MA
In this town-wide celebration, you begin at the West Brookfield Town Common where the tree lighting will be held. You’ll find picture with Santa, horse and carriage rides, and entertainment for the kids like gingerbread people and house decorating. Shuttles will be available to take you around town where local businesses are opening there doors and West Brookfield Elementary is holding a holiday market with over 60 vendors.
Webster Holiday Parade
Saturday, December 13 at 5:00 p.m. | Webster, MA
The town of Webster is hosting a holiday parade with the route TBD.
Auburn Recreation and Culture Holiday Craft Fair
Saturday, December 13 from 9:00 a.m. – 4:00 p.m. | Auburn High School, 99 Auburn St, Auburn, MA
This huge craft fair in Auburn will have over 190 vendors! From food trucks, artisans, and local nonprofits, you’re guaranteed to discover some great holiday gift ideas.
Douglas Winter Stroll
Saturday, December 13 from 3:00 p.m. to 6:00 p.m | Main Street, Douglas, MA
Back in Douglas, we have another holiday shopping event. The Winter Stroll is the night when the businesses of Main Street and beyond open their doors for festive winter fun. At the Simon Fairfield Public Library, warm up with hot cocoa and cider while the kids can meet and send letters to Santa, make crafts, listen to story time, and more. Find food, hot cocoa and cider, giveaways, and live music in several different places while you stroll. There is so much to enjoy at this event.
Old Sturbridge Village Christmas by Candlelight
November 28-30, December 5-7, 12-14, 19-23, and 27-30 | Old Sturbridge Village, 1 Old Sturbridge Village Rd, Sturbridge, MA
Experience holiday history by candlelight at Old Sturbridge Village. Learn how early settlers carried out holiday traditions like nutcrackers, Christmas stockings, and toys. Meet Santa and Mrs. Claus, listen to story time and live music, warm up with soup, hot cocoa or cider, and be a part of a Gingerbread House decorating contest! Ticket prices vary by date and age. Children under 3 are free.
Southwick’s Zoo Winter Wonderland
November 22 through December 28 | Southwick’s Zoo, 2 Southwick Street, Mendon, MA
Journey through New England’s largest zoo and behold the dazzling lights displays featuring more than 4 million lights. Accompanied by a meet & greet with Santa and Mrs. Claus, a sing along with the characters of Disney’s Frozen, and a Holiday Variety show full of entertainment. Tickets purchased online are $21 for adults and $13 for kids 3-12 (children under 2 years get in for free).
Boston Holiday Celebrations
Snowport Holiday Market
Open daily November 7 – December 28 | Seaport District, 65 Northern Ave, Boston, MA
Boston’s iconic winter pop-up shop in the Seaport district boasts more than 120 vendors. It’s the largest open air market in the city. You can shop everything from food and cocktails to holiday decor and gifts. Snowport’s mascot, Betty the Yetti, makes appearances for photo ops. Special pop-up shops appear all throughout the season. You can even take curling lessons or curl on your own with friends (the winter sport, not the thing you do with your hair). And if all that isn’t enough, local retailers open their doors for an indoor shopping Holiday Stroll on December 13, from 1:00 p.m. to 4:00 p.m.
Faneuil Hall Tree Lighting at Quincy Market
Saturday, November 22 from 2:00 p.m. to 7:00 p.m. | Faneuil Hall, Boston, MA
Enjoy the lighting of the 50 foot tall tree at Boston’s Faneuil Hall at 6:00 p.m. sharp. Kick off the season with live entertainment, special guests (maybe Santa??), and treats from the shops around Faneuil Hall and Quincy Market. This year’s entertainers include Commonwealth Shakespeare Co., North End Music & Performing Arts Center, BSoma Dance Company, Boston Children’s Chorus, Boston Ballet, and The Femmes!
Lighting of the Trellis at Christopher Columbus Park
Monday, November 24 from 5:00 – 6:00 p.m. | 110 Atlantic Avenue, Boston, MA
The city of Boston lights up the 260 foot long trellis at Christopher Columbus Park for the holidays. Come along Boston’s historic waterfront for this celebration which will include musical performances, special guest appearances from Santa Claus and Rudolph the Red-Nosed Reindeer, eggnog from H.P. Hood, hot chocolate and cookies from the Boston Marriott Long Wharf, and clam chowder courtesy of Joes Waterfront.
Winthrop Chamber of Commerce’s Small Town Big Lights
Friday, November 28 from 3:00 p.m. 6:00 p.m and Saturday, November 29 from 11:00 a.m. to 4:00 p.m. | Winthrop Center, Winthrop, MA
Winthrop’s tree lighting in center of town on Friday, November 28 will include vendors, carolers, horse and buggy rides, and a DJ. Webster First is a sponsor for this event’s carolers and the photographers to help capture all the night’s magic. New this year – the event continues into Small Business Saturday on the 29th where you can take a Jolly Trolley ride around town to “hop & shop” at local businesses. Support small this holiday season!
SoWa Winter Festival
November 28 through December 28 (closed on Christmas and Christmas Eve) | SoWa Power Station, 550 Harrison Ave, Boston, MA
New England’s largest indoor holiday market. Stay warm while you shop with more than 120 vendors at SoWa Winter Festival. Admission tickets are $10 and on-site parking is $10, but children under 12 are free! They are closed on Mondays, Christmas Eve, and Christmas Day.
Copley Square Tree Lighting & Grand Reopening
Monday, December 1 from 4:00 – 6:00 p.m. | 560 Boylston Street, Back Bay, Boston, MA
This celebration will feature a guided tour through the newly renovated Copley Square and will feature musical performances by vocalist Joelle James, the Boston Children’s Chorus and the Boston Pops Esplanade Brass Ensemble. Santa and Rudolph will make appearances and you get the chance to have cookies and photos with them in Fairmont Copley Plaza after the event. This is a free event.
Boston Common Tree Lighting
Thursday, December 4 from 6:00 – 8:00 p.m. | Boston Common, 139 Tremont Street, Boston, MA
At the 84th annual lighting of the trees on Boston Common, WCVB Channel 5 and the Boston Globe will be there to broadcast the event live. Mayor Wu will be joined on stage by Santa Claus and Rudolph. Samples of refreshments and giveaways will be available. Immediately following this lighting, head to Charlesgate Park to watch the Commonwealth Avenue Mall light up.
Lighting of the Trees on the Commonwealth Ave Mall and Charlesgate Park
Thursday, December 4 at 8:15 p.m. | Arlington Street and Commonwealth Avenue, Back Bay, Boston, MA
Join the City of Boston to light the Mall immediately following the Boston Common tree lighting.
Saugus Holiday Lighting and Christmas Market
Friday, December 5 | Town Hall and First Congregational Church, Central St, Saugus, MA
Saugus lights up their trees at the town hall on December 5, and right across the street at First Congregational Church who will be holding a Christmas Market complete with food, crafts, gifts, raffles, and more!
Hopkinton Caroling on the Common & Photos with Santa
Saturday, December 6 from 2:00 – 4:30 p.m. | Hopkinton Town Common, 1 Ash St, Hopkinton, MA
Grab your photos with Santa, shop around the Holiday Market, and fill up at food trucks while you listen to carolers and watch the common light up. Discover more activities at this free event hosted by the Hopkinton Girl Scouts.
Boston’s Winter Fest
Saturday, December 6-7, 12-14, and 19-30 (closed Christmas Even and Christmas Day) | 100 Hood Park, Boston, MA
According to their website, Winter Fest is Boston’s “premiere winter carnival.” A festival of lights complete with an ice castle, Santa’s Workshop, and artisan village, beer and wine, hot food and drinks, and more! Entry fees are $5 and parking is free for 3 hours at the Hood Park Garage.
Frozen Fire Festival
Friday, December 12-14 | The Anchor, 1 Shipyard Park, Boston, MA (Additional dates and location in Salem, MA TBD)
This event is packed with winter fun like food and beverages, an artisan market, fire installations, and curling. It has entertainment the likes of live music, fire performers, cirque performers, and live ice sculpting demonstrations. Plus, book a private VIP Igloo for your group to hang out and keep warm.
Harvard Square Holiday Fair
December 12-14 and December 19-21 | Corner of JFK St & Winthrop St, Cambridge, MA
Find artists from far and wide at this two weekend long craft fair in Boston. Find handmade, original artworks and crafts that would make great holiday gifts while supporting small businesses.
You might also like: Massachusetts Fall Festivals
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Disclaimer: Webster First was not paid to endorse or evaluate the events mentioned in this post.