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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 Thanksgiving around the corner and 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. Get into the Christmas spirit in this idyllic setting, starting with tree trimmings and lightings as early as Thanksgiving weekend. Throughout the month, there are Christmas strolls and caroling in many villages, and Santa has even been known to arrive aboard a Coast Guard vessel!

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

On the Cape, tree lightings, holiday strolls and caroling are among the holiday festivities.

Brewster: Brewster for the Holidays runs from December 2 - December 4. The kickoff includes live music and treats for the kids on Friday, December 2, at 4 pm at Drummer Boy Park where WeNeedaVacation.com will illuminate the Holiday Tree (Bring a toy to donate to local charity). Other events include the Brewster Band Concert at the Brewster Baptist Church on Friday, December 2nd; Saturday from 10AM - 4PM...Holiday Arts & Crafts Show in the Eddy Elementary School. 50 exciting vendors and plenty of free parking. Free admission; the Chowder Festival from 12-2 pm on Sunday and the Family Gala Sunday at the Museum of Natural History from 2-4pm. And on Saturday night from 6 - 10 PM, the Holiday Dinner Dance presented by the Brewster Historical Society at Captain's Golf Course. On Sunday attend the Family Gala at the Museum of Natural History from 2-4pm. Music, crafts, home-made sweets buffet and photos with Santa! FREE admission for everyone!

Centerville: The Annual Main Street Christmas Stroll will be held from 3-6 pm on Sunday, December 4th.

Chatham: The Christmas Stroll will be held December 9 through December 10 and begins with a tree trimming and lighting ceremony in Sears Park at 4:30 pm on Friday.

Falmouth: "Holidays-by-the-Sea" will run from December 2 -December 4 and will include the Annual Falmouth Christmas Parade on Sunday at noon. Other events include the Holiday Carol Sing at Nobska Lighthouse at 5:30 pm on Friday and the Annual Lighting of the Falmouth Village Green at 7 pm on Saturday.

Harwich/West Harwich/Harwich Port: Christmas in Harwich will be held the weekend of December 2 -December 4. Lots of entertainment, open houses, a Christmas stroll, tree lighting and carol singing are planned.

Mashpee: The Annual Mashpee Christmas Parade steps off from Mashpee Commons at 5:30 pm on December 10.

Orleans: Join the Orleans Stroll for Caroling and Tree Lighting on the Village Green on Christmas in Orleans on Sat., Nov. 26 at 4:45pm. On Saturday December 3 at 9:00am, Join the Santa Stampede 5K & Family Fun Run which is held throughout scenic East Orleans. Kick off your holidays at our festival fun run! See Santa run!

Osterville: celebrates the 47th Annual Christmas Open House & Stroll throughout the traditionally decorated village on December 9, from 10am - 9pm.

Provincetown: Start the season early on Nov. 23 at the traditional ceremony as the Pilgrim Monument is illuminated in grand style for the remainder of the season. December 2 – December 4 will mark the annual "Holly Folly" celebration.

Sandwich: "Holly Days in Sandwich" presents a series of great events including: The Sweet Sandwich Cookie Stroll on December 10, the "Lighting of the Littlest Christmas Tree," on November 27 at 5 pm; the Community Carol Sing at First Church on December 2 at 7 pm; and the Holly Day Home Tour on December 11 from 12 pm to 4 pm.

Heritage Gardens presents, Gardens Aglow A Treasured Holiday Tradition runs November 25th – December 18th - a treasured holiday family tradition, transforms Heritage into Winter Wonderland with more than ten miles of holiday lights adorning the gardens and woodlands to create a twinkling wonderland.

Yarmouthport: Celebrate our Christmas Stroll with caroling and the tree lighting on the Common on Sunday, December 4th at 1pm -4:15pm .

Chatham: Ring in the New Year at First Night Chatham, an annual celebration of the arts. Kids activities begin at 1 pm. Music, noise parade, midnight fireworks and much more go on throughout the day and night.

Sandwich: Experience First Night Sandwich on December 31.-A festival for the arts with music and beautiful creations, First Night Sandwich begins at 4pm and ends with a Grand finale at 8pm. Performances and hands-on activities focus on children, children’s participation and family entertainment.

While all of Cape Cod and the Islands are enchanting during the holiday season, perhaps the best known Christmas celebration is held on Nantucket Island. The Annual Christmas Stroll Weekend, held December 2 - 4 is part of Nantucket Noel which runs November 25 - January 2 2016.The festivities begin on the Friday evening after Thanksgiving with the lighting of over 150 Christmas trees in Nantucket's historic downtown. Residents and visitors alike gather to watch while the cobblestone byways become illuminated with color and light. Community caroling follows. Santa and Mrs. Claus arrive on the Island via a Coast Guard vessel and ride up Main Street in a horse-drawn carriage accompanied by the Town Crier. If you are on the Island over the Thanksgiving week, be sure to catch the Nantucket Historical Association's Annual Festival of Wreaths from Wednesday, November 23rd & November 25th -27th at the Whaling Museum.

Visit Nantucket to celebrate New Year’s. Enjoy first night on Nantucket as the Island community hosts four days of holiday festivities from December 30 - January 2

On Martha's Vineyard, you can start the season early in a non-commercial way the day after Thanksgiving at the Fall Festival at Felix Neck. The Festival includes hay rides, guided walks, food, music, and more. Then don't miss the annual Christmas in Edgartown on December 8 - 11 beginning with the lighting of the Edgartown Lighthouse followed by the annual Santa Parade, the lighting of the Christmas Tree in the Park, and music. The celebration runs throughout the weekend and includes the Minnesingers Holiday Family Concert on December 9 at 8:00 pm and December 10 at 4 pm at the Old Whaling Church.

On November 30, Oak Bluffs starts celebrating the season with the traditional tree lighting and music heralding the arrival of Santa Claus. The Featherstone Center for the Arts invites you to the Annual Holiday Show, which will run from November 19 to December 18.

The annual Christmas Faire will be held at The First Congregational Church of West Tisbury on December 10. On December 10, stop by The Vineyard Artisan Holiday Festival from 10 am until 4 pm at the Grange Hall in West Tisbury.

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.