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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 6 - December 8. The kickoff includes live music and treats for the kids on Friday, December 6, at 4 pm at Drummer Boy Park where WeNeedaVacation.com will illuminate the Holiday Tree (please bring a toy to donate to local charity). Other events include the Brewster Band Concert at the Brewster Baptist Church on Friday, December 6 at 7 pm; Saturday, December 7, Breakfast with Santa 8:30 & 10:30, Ocean Edge Resort & Golf Club, 2907 Main Street, in the Carriage House. Two seatings, space limited, advance tickets required; Photos with Santa from 1:00-4:00, First Parish Brewster Universalist Unitarian Church, 1969 Main Street. Photos with humans 1 - 3 pm; with Pets 3 - 4 pm. You bring the camera and we will provide the Santa! Cookies, Pies, Holiday Decorations, Fiber Crafts and Holiday Greenery will be for sale.

Centerville: The Annual Main Street Christmas Stroll will be held from 3 - 6 pm on Sunday, December 8th.

Chatham: The Christmas Stroll will be held December 13th and begins with a tree trimming and lighting ceremony at Kate Gould Park. Meet at Carmine’s Pizza parking lot as Santa leads us caroling down to the Annual Tree Lighting in Kate Gould Park at 5:45 pm.

Join the Chatham Merchants Association at the Chatham Wayside Inn for Breakfast with Santa during Christmas Stroll Weekend! There will be a homemade breakfast courtesy of the Chatham Wayside Inn and Wild goose Tavern, children’s entertainment, and the main event . . . Santa! Tickets are required and the event will be held December 14th from 8:30-10:30 a.m. at The Wayside Inn.

Dennis: The Dennis Village Stroll will be on December 8th from 12 p.m. – 4 p.m., Rt. 6A in Dennis Village. Enjoy hayrides & trolley rides, Christmas tree lighting, face painting, village stroll (visit all the shops), silent auctions, toys and food donations, Santa & Mrs. Claus and so much more. There will be music at the Village Green Bandstand and many special events.

Harwich/West Harwich/Harwich Port: Christmas in Harwich will be held the weekend of December 6 - December 8. 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 7.

Orleans: Join the Orleans Stroll for Caroling and Tree Lighting on the Village Green on Christmas in Orleans on Sat., November 30 at 4:45pm. On Saturday December 7 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!

Osterville: celebrates the 49th Annual Christmas Open House & Stroll throughout the traditionally decorated village on December 6, from 10am - 9pm.

Provincetown: Start the season early on November 27th at the traditional ceremony as the Pilgrim Monument is illuminated in grand style for the remainder of the season. The Lobster Pot Tree, built with over 100 lobster pots, will be lit on November 30 at 5:30 pm. December 5 - December 8 will mark the annual "Holly Folly" celebration.

Sandwich: "Holly Days in Sandwich" presents a series of great events including: the "Lighting of the Littlest Christmas Tree," on December 1 at 5 pm; the Community Carol Sing at First Church on December 6 at 7 pm; and the Holly Day Home Tour on December 8 from 12 pm to 4 pm.

Heritage Gardens presents, Gardens Aglow A Treasured Holiday Tradition, runs November 29 - December 29 — 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 15th at 1pm to 4 pm.

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 4 pm and ends with a Grand finale at 8 pm. 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 6 - December 8 is part of Nantucket Noel which runs November 28 - December 31. 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 November 27th - December 1st 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 12 - 15 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 13 at 8:00 pm and December 14 at 4:00 pm at the Old Whaling Church.

On November 28, 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 Gift Show, which will run from November 15 - December 13.

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.