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Festive Holiday Events and Ways to Give Back This Season in Massachusetts

Massachusetts is regarded as a dream destination for summer getaways, so visitors may be pleasantly surprised to learn that it only gets better in the off-season. Even in brisk and snowy weather, people travel from near and far to experience the charm of our communities in all their holiday glory. The season also brings an energy of giving, sparkling light displays, and a whole calendar of events (both annual and new) that never fail to put us in the holiday spirit. 

This year, we are proud to support a few of Massachusetts’ greatest seasonal attractions that benefit local organizations that are close to our hearts and make the holidays a bit brighter for those in need. We hope you will join us in the spirit of giving!

Gibson Sotheby's International Realty


Harwich Port Stroll: 5:30pm, Various locations in Harwich

The annual Harwich Port Stroll kicks off with a tree lighting and caroling in Doane Park with the Harwich Elementary School Chorus, Pilgrim Masonic Lodge, and Pilgrim Congregational Church. Santa’s arrival by fire truck to the Harwich Chamber of Commerce Porch is sure to draw a crowd. And thanks to the talented musicians of the Harwich Town Band, there will be no shortage of alluring performances. Revel in miles of holiday lights in each of Harwich’s seven villages as you shop for holiday gifts and, if you can, bring an unwrapped toy, food, or cash or gift card donation for the Harwich Fire and Police to give to our neighbors in need. Learn more here.

Manchester-by-the-Sea Stroll: 4-8pm, Various locations in Manchester-by-the-Sea

Enjoy a festive night of holiday shopping by the sea as you support the Cape Ann Chamber of Commerce. Peruse holiday gifts at local boutiques, charming antique shops, and independent art galleries that will have you glad to leave behind long lines and crowded parking lots. While you shop, don’t forget to collect stamps in your Holiday Stroll Passbook and turn in your completed Passbook at Boo-Bird by 8:15pm for a chance to win $200, $100, or $50 gift cards to Cape Ann businesses. Learn more here

Provincetown Holly Folly Weekend: Through December 3, Various times and locations in Provincetown 

The nation’s original LGBTQ+ holiday celebration first began in 1997. 26 years later, more than 30,000 visitors travel from far and wide to get a jumpstart on holiday shopping and participate in a spirited series of holiday parties, a Santa-themed fun run down Commercial Street, and other merrymaking moments. Learn more and see the full lineup of events here

Padanaram Holiday Stroll: 4-8pm, Dartmouth Maritime Center, 1 Bridge Street, Dartmouth

Discover the charm of South Dartmouth as you stroll through its scenic streets lined with local shops decked out for the holidays. The Gibson Sotheby's International Realty Dartmouth Office will be turned into a cookie-making shop for the masses to enjoy. There will be a full schedule of local traditions to partake in, plenty to eat and drink, and no shortage of holiday spirit to celebrate—with picturesque Padanaram as the backdrop. Be sure to gather by the Maritime Center and catch the third annual Buoy Tree Lighting: a stunning ceremony that will illuminate a coastal-inspired Christmas “tree” through early January. Fifty of the most creative buoys decorated by local community members will be auctioned off and 100% of the proceeds will benefit the Friends of Jack Foundation—a non-profit organization that establishes healthcare programs for children on the South Coast and in Rhode Island. This enchanting tradition promises to fill you with the spirit of the season! Learn more here.

The Brewster Band Annual Holiday Concert: 7pm, Brewster Baptist Church, 1848 Main Street, Brewster

Peggy Farber, an associate at Gibson Sotheby’s International Realty in Brewster, joins us in sponsoring this cherished holiday celebration at the Brewster Baptist Church. Join us for performances filled with holiday music favorites. Admission is free and donations will be accepted to benefit Emerald Hollow Therapeutic Riding Center. 

Christmas Tree


Wellesley Holiday Stroll: 12-6pm, Various locations in Wellesley

Experience the spirit of the season at Wellesley’s annual Holiday Stroll. Spend all afternoon wandering through Wellesley Square and browsing its charming shops before partaking in a prize-filled scavenger hunt while carolers rove the neighborhood. The stroll will conclude with sleigh rides with Santa Claus and a Christmas tree lighting at the Wellesley Square Fire Station


Chatham Christmas Stroll: Various times and locations in Chatham

Join in the annual tradition of this festive community event! The Chatham Christmas Stroll kicks off on Friday with a light parade from Carmine’s Pizza to Kate Gould Park, followed by an annual tree lighting with Santa Claus. There will be carolers and festive characters roaming Main Street and all the shops and restaurants will be bustling with holiday cheer. Learn more here

Holiday Lights


Newburyport Holiday House Tour: 10am-4pm, Various locations in Newburyport

Hoping for a rare glimpse into Newburyport’s finest private residences and unique spaces? Your self-guided tour will lead you through several homes in Newburyport, all decked out both inside and out for the holidays. Come and experience a day full of holiday magic. This tour is appropriate for children ages 12 and up. All proceeds will benefit the Anna Jaques Hospital Aid Association. Purchase tickets and learn more here.

Cohasset Village Holiday Stroll: 4:30pm-7:30pm, Cohasset Chamber of Commerce, 13 Elm Street, Cohasset

Experience the idyllic town of Cohasset aglow in lights and holiday splendor. The Cohasset Chamber of Commerce will once again host and present a Holiday Stroll filled with family-friendly events, live music, exciting in-store shopping experiences, and even a sighting of Santa. Take a holiday hayride through Cohasset Village, and don’t forget to stick around for the annual tree-lighting ceremony. Learn more here

Holiday Lights on the Water


Dennis Village Stroll: 12-3pm, Dennis Village Green and Route 6A, Dennis

The Dennis Village Stroll never fails to put us in the holiday spirit. Have the kids dressed in their best holiday attire to sit with Santa, who will be in person at our Dennis office location at 563 Main Street. Just half a mile down the road, the Cape Cod Museum of Art will host a special pop-up holiday gift show where you can browse one-of-a-kind handmade jewelry, pottery, and more and enjoy plenty of cider, cookies, and crafts.

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