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!
DECEMBER 1
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.
DECEMBER 3
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.
DECEMBER 8
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.
DECEMBER 9
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.
DECEMBER 10
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.