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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

Brewster for the Holidays Tree Lighting at Drummer Boy Park

December 3rd, 4pm

Rockin’ Round the Christmas Tree in Drummer Boy Park—the Brewster town tree and windmill lights will be lit for the holiday season. There will be carol singing and Santa will arrive by Fire Truck! Please bring an unwrapped toy for the Brewster PTO Toy Drive. Sponsored by Leighton Realty, WeNeedaVacation.com, and the Brewster Historical Society.

Breakfast with Santa at Ocean Edge

December 4th. Two Seatings: 8:30am – 10:00am & 10:30am – Noon

Tickets to this event includes a full buffet breakfast and each child ticket will receive a voucher for arts & crafts. (Additional crafts for sale). Bring your camera for pictures with Santa (for a donation, please!) All proceeds will benefit local children & families as part of our Brewster Holiday Hope fundraising drive.

Chatham

Christmas Stroll & Tree Lighting

December 10th at 5:45pm Kate Gould Park

There will be carolers, entertainment, festive characters throughout Main Street. All of our shops, restaurants and businesses will be open and bustling with holiday cheer!

Photos with Santa

December 11th, 10am – 1pm at the Chatham Wayside Inn.

Harwich

Harwich Port Stroll

December 3, 5:30pm – 9:00pm

At 5:30 there will be tree lighting and caroling by the Harwich Elementary School and Pilgrim Congregational Church will happen in Doane Park. At 6:05pm Santa arrives by firetruck (please bring a donation for Homeless for the Holidays), from 5:30pm – 9:00pm, stroll through Harwich Port businesses enjoy holiday shopping and dining

Trolley to Christmas Town

December 4th & 5th, 5:15pm, 5:45pm, 6:15pm, 6:45pm and 7:15pm

Mashpee

Annual Mashpee Christmas Parade

December 11th, 5:30 pm

This unique, nighttime event is where every float is brilliantly illuminated in the spirit of the season. Award-winning bands dazzle the crowds with festive music, holiday garb, and of course more lights!

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.

Orleans

Breakfast with Mrs. Claus & Santa Arrives by Boat

November 27th, 9 am at the Orleans Yacht Club

The day begins with sweet treats at the Breakfast with Mrs. Claus at the Orleans Yacht Club. This event is free, but donations will be accepted. In addition to delicious donuts and coffee from the Hole In One restaurant, Mrs. Claus will be on hand for photo opportunities as families wait for Santa, who arrives at 10 a.m. to meet and greet his fans and pose for pictures. We’ll be outdoors this year in heated tents. Kids can follow Santa to Snow’s Home & Garden, 22 Main St., where he will listen to gift requests and take pictures with the little ones.

Santa Stampede 5k and Family Fun Run

December 4th, 10:30 am

Join the Stampede! A family-friendly event for all ages. Presented by the Orleans Chamber of Commerce, will benefit the Lower Cape Outreach Council and Homeless Prevention Council, more info here.

Osterville

Osterville Annual Christmas Open House and Stroll

December 10th, 5pm – 9pm

Join us for our 52nd Annual Christmas Open House & Stroll. Special events throughout the village.

Falmouth

Annual Falmouth Christmas Parade

December 5th, 12pm

The theme of the 2021 parade is "Together for Christmas"! parade featuring theme decorated floats, marching bands, live animals, costumed characters and Santa Claus!

2019 Parade photo from the Cape Cod Chamber website.

Sandwich

Sandwich Community Caroling

December 3rd, 7pm

Gather at the steps of the First Church of Christ, 136 Main Street Sandwich at 7:00 p.m. for the annual Carol Sing. Santa Claus will make a brief appearance.

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

Nantucket Annual Tree Lighting

November 26th, 4:30pm

The Festival of Trees

December 3rd 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.

Martha's Vineyard

Christmas in Edgartown

December 9th through the 12th

Save the date for our 40th Annual Christmas in Edgartown. After last year’s “magically modified” celebration, we have high expectations for this exciting milestone. Traditionally one of New England’s most charming holiday weekend festivals, Edgartown over the holidays will not disappoint.

Holiday Gift Show

December 12th through the 16th

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 WeNeedaVacation.com 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.