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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 4 -December 6. The kickoff includes live music and treats for the kids on Friday, December 4, at 4 pm at Drummer Boy Park where WeNeedaVacation.com will illuminate the Holiday Tree (Bring a toy or canned good to donate to local charity). Other events include the Brewster Band Concert at the Brewster Baptist Church on Friday, December 4th; 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.

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

Chatham: The Christmas Stroll will be held December 11 through December 12 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 4-December 6 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 4-December 6. 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 12.

Orleans: Join the Orleans Stroll for Caroling and Tree Lighting on the Village Green on Christmas in Orleans on Sat., Nov. 28 at 4:45pm.

Osterville: celebrates the 44th Annual Christmas Open House & Stroll throughout the traditionally decorated village on December 11, from 10am - 9pm.

Provincetown: Start the season early on Nov. 25 at the traditional ceremony as the Pilgrim Monument is illuminated in grand style for the remainder of the season. December 4 – December 6 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 November 28, the "Lighting of the Littlest Christmas Tree," on November 29 at 5 pm; the Community Carol Sing at First Church on December 4 at 7 pm; and the Holly Day Home Tour on December 6 from 12 pm to 4 pm.

Yarmouthport: Celebrate with caroling and the tree lighting on the Common on Sunday, December 6 at 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 4 - 6 is part of Nantucket Noel which runs November 27 - 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 25 through Sunday, November 29 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 10-14 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 11 at 8:00 pm and Saturday December 12 at 4 pm at the Old Whaling Church.

On December 2, 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 22 to December 21.

The annual Christmas Faire will be held at The First Congregational Church of West Tisbury on December 5. On December 12, 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.