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Celebrate the Holiday Season on Cape Cod and the Islands

Holiday events make Cape Cod vacation rentals just as fun in the winter as in the summer! With the holiday season upon us, come experience the beauty and traditions of Cape Cod and the Islands, as well as the magical atmosphere that is unique to the area.

Santa arrives by boat during Christmas in Orleans, Cape Cod
Santa arrives by boat during Christmas in Orleans


Brewster for the Holidays Tree Lighting at Drummer Boy Park

For a virtual Illumination Ceremony this year, please tune in to Cable Channel 99, the Brewster Chamber of Commerce website or the Brewster for the Holidays website. The Brewster town tree and windmill lights at Drummer Boy Park are lit for the holiday season. And Santa arrives to spend time in Brewster!!! Sponsored by Leighton Realty,, and the Brewster Historical Society.

Pictures with Santa at Lemon Tree Village

December 5th, 11am-1pm

Have a socially distant visit with Santa and share your Holiday wish list! Santa will be waiting to greet you. Don’t forget a camera to capture the event! Face coverings required while visiting Lemon Tree Village. And in the spirit of the season, there will be food items collected for the local food pantry, so everyone is encouraged to bring a non-perishable food item.

This event is free to the public and sponsored by the Brewster Chamber of Commerce and the merchants of Lemon Tree Village.

Bayside Bright Lights Celebration

December 19th, 4pm-6pm at Eddy Elementary School

Brewster Recreation is partnering with other town departments and local businesses to create a wonderful Holiday celebration. This new event will consist of a drive around the Eddy School with Christmas lights, Holiday themed inflatables, winter themed lawn decorations, lit up police cars and fire engines, and of course….Santa! Although you will not be able to sit on his lap and talk to him, you can give him a wave when you drive by. Please bring your Christmas wish list to put in the North Pole mail box for Santa. And don’t forget to grab your goody bag on the way out!

Registration for this event is available online.


Virtual Tree Lighting December 11th at Chatham Cape Cod's Facebook Virtual Event

Selfies with Santa December 12th, 10am-12pm at the Chatham Community Center

While Chatham will not be holding their annual Christmas Stroll, there will be a variety of events hosted throughout the season! Sign up and Stop by the Community Center for Selfies with Santa, check out the virtual tree lighting, or participate in their holiday giveaways starting December 1st!


Dennis Holiday Lights Competition

Dennis Holiday Lights is a friendly competition throughout the Town of Dennis for residents and businesses alike. You do not need to be a member of the Dennis Chamber of Commerce to register and participate!

The Dennis Chamber of Commerce is looking for businesses and residents to light up the town of Dennis for this fun and interactive light contest. Everyone, near and far, is encouraged to drive around to check out the lights and vote for their favorite display in the three categories. Check Visit for more information.


Mashpee Chamber's Season of Illuminations

Mashpee Rotary

The Town of Mashpee and the Mashpee Chamber of Commerce are proud to present the spectacular light display at the Mashpee Rotary. This Holiday tradition means more than ever this year as we come together as a community to share Holiday spirit.


Santa Stampede 5k and Family Fun Run

Virtual Event held throughout December

Join the Stampede! A family-friendly event for all ages. We couldn’t let the community down, so the Santa Stampede will be a virtual run, handled by the platform This is the 8th year for the Stampede!


Various holiday events will be held on Saturdays throughout the season including carolers, live jazz, and special sales. View the lights and decorated trees throughout the village.


57th Annual Falmouth Chamber of Commerce Christmas Parade “Home for The Holidays”

The Falmouth Chamber will air the pre-taped 57th Annual Falmouth Chamber of Commerce Christmas Parade “Home for The Holidays” at noon on Sunday December 6th on Falmouth Community Media Center! Tune in to this time-honored tradition, which will be kept alive virtually in 2020. Due to COVID restrictions, this event will not be open for public viewing.

2019 Parade photo from the Cape Cod Chamber website.


Last Best Craft Fair 2020 Virtual Edition

Shop Local. Shop Safe. The Sandwich STEM/SHS PTSA is hosting the 26th Annual Last Best Craft Fair virtual edition. The online fair will run from November 14 - December 5th. This is a great opportunity to support local artisans and crafters while looking for unique handcrafted items for everyone on your holiday shopping list. Go to:

Garden's Aglow at Heritage Museums and Gardens

Every Friday, Saturday, and Sunday through December 26th, 4:30pm-8:30pm

"This year Heritage will continue the celebration of lights that has become a treasured holiday tradition with a fully outdoor experience. This event features beautiful light displays throughout the gardens, as well as many activities throughout the grounds. Roast marshmallows at the fire pits. Participate in a reindeer scavenger hunt. View a new addition to the event, The McGraw Family Garden of the Senses that features a stunning model train display. Savor festive treats and hot drinks at the Magnolia Café. Visit with Santa Claus at the Outdoor Stage. Find fun photo opportunities throughout the grounds. Enjoy Cape Cod Donuts, a warming area, games, and holiday music at the Parade Field. Find fabulous holiday gifts in The Shop. Stroll the gardens with family and friends, and enjoy Heritage in a whole new light."

Gardens Aglow photo selected from Heritage Museums and Gardens website.


Nantucket Annual Tree Lighting Virtual

November 27th, 4:30pm Virtual

This year's virtual tree lighting will be available at Nantucket Community Television.

The Festival of Trees

November 27th through December 31st at The Whaling Museum

The Festival of Trees is the NHA’s highly anticipated holiday tradition that transforms the Whaling Museum into a festive winter wonderland for the entire month of December! This event features community-crafted trees designed by local merchants, nonprofit organizations, artists, and children. The NHA is extremely grateful for the involvement and support of the many individuals and organizations that contribute to the success of the Festival of Trees. Your creativity and talent make it all possible. To ensure the safety of our visitors and the community the Festival of Trees will be slightly adjusted to adhere to safety protocols and allow for more viewing time for visitors. No Preview Party will be held.

Martha's Vineyard

Christmas in Edgartown

December 10th through the 13th

The Festival of Trees is the NHA’s highly anticipated holiday tradition that transforms the Whaling Museum into a festive winter wonderland for the entire month of December!

Holiday Gift Show

The Holiday Gift Show is the perfect holiday shopping destination with gifts for everyone (and yourself) - handmade creations including paintings, photography, pottery, crafts, jewelry, knitwear, clothing, purses, accessories, soaps, dog goods, ornaments, cards, calendars and stocking stuffers. Buy local and support local artists all while supporting Featherstone as well! This year we are increasing the artists' commission to 60% while 40% of proceeds benefit the art center. 'Tis the season for supporting the arts community!

About Becky Fischer

About Becky Fischer: I have worked for since 2003. Currently serving as Marketing Manager, my position entails collaborating on all print and social media marketing efforts as well as the company's valuable relationship with 17 local Chambers of Commerce. In addition, I provide photography, video, and consultation services to vacation rental homeowners, and have photographed over 300 homes on the Cape and Islands. My husband and three children moved to Brewster in 2006. I grew up outside of Boston, spent summer vacations on Nantucket, and was married in Orleans. My favorite activities on the Cape are walking on the CCRT, deep breaths at the beach, and working with my community to support the schools and local events.