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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

December 2nd, 4:00 p.m.

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,, the Brewster Historical Society, and 101.f Koffee fm.

Breakfast with Santa at Ocean Edge

December 3rd. Two Seatings: 8:30 a.m. – 10:00 a.m. & 10:30 a.m. – Noon

Tickets to this event include 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.


Christmas Stroll & Tree Lighting

December 9th at 5:45 p.m. Kate Gould Park

There will be carolers, entertainment, festive characters throughout Main Street until the 11th. All of our shops, restaurants and businesses will be open and bustling with holiday cheer!

Breakfast & Photos with Santa

December 10th, 8:30 a.m. at the Chatham Wayside Inn.


Dennis Village Stroll

December 11th, 11:00 a.m. to 3:00 p.m.

Meet at the gazebo and enjoy music, food, and some holiday shopping!

Santa Arrives at Patriot Square

December 3rd, 12:00 p.m. to 3:00 p.m.

Watch Santa arrive by helicopter!


Christmas in Harwich

Festivities Starting Friday December 2nd

Christmas in Harwich begins with the Harwich Port Stroll Friday night with the Annual tree lighting and Santa arriving by Fire Truck. There will be Holiday sales and specials with Harwich Port businesses and organizations open houses, music, and good cheer. There will be Carolers, Harwich Town Band, Holiday Elves and more

Trolley to Christmas Town

December 2nd - 4th, 5:15 p.m., 5:45 p.m., 6:15 p.m., 6:45 p.m. and 7:15 p.m.


Annual Mashpee Christmas Parade

December 10th, 5:30 p.m.

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 Rotary Season of Illumination

Daily, Friday, November 25, 2022 - Sunday, January 1, 2023

The Town of Mashpee and the Mashpee Chamber of Commerce are proud to present the first holiday lights event at Cape Cod Children's Museum! FREE drive thru community event with a spectacular musical light show. Even includes a Rudolph themed wall of inflatables.


Breakfast with Mrs. Claus & Santa

November 26th, 8:30 a.m. - 10:00 a.m. at the Orleans Yacht Club

The days are shorter but brighter during the holidays in Orleans. The season kicks off on Saturday, Nov. 26 with Breakfast With Mrs. Claus at the Orleans Yacht Club followed by Santa’s arrival from the North Pole. Enjoy donuts and coffee from Hole-in-One while the little ones have their pictures taken with Mrs. Claus. Santa arrives by boat at 10am!

Santa Stampede 5k and Family Fun Run

December 3rd, 9:00 a.m.

Join the Santa Stampede, the annual 5K race in East Orleans! * Saturday, Dec. 3 at 9am * Kids 12 and under can run the Mini-Claus one-mile race for FREE at 10am. * Runs start/end at the Barley Neck * More than 25 prizes, including fastest men & women * Run in holiday costume and enter the Holiday Costume Contest! * T-shirts while supplies last.

Orleans Winterfest

Saturday November 26th, 5:00 p.m.

Candlelight stroll down Main Street. Party afterwards at Artists Cottages.


Osterville Annual Christmas Open House and Stroll

December 9th, 5:00 p.m. – 9:00 p.m.

Join us for our 53rd Annual Christmas Open House & Stroll. Special events throughout the village.


Annual Falmouth Christmas Parade

December 4th, 12:00 p.m.

The theme of the 2022 parade is "Holiday Traditions." This festive event will feature decorated floats, marching bands, live animals, costumed characters and Santa Claus!

Falmouth Holidays by the Sea

December 2nd - 4th.

Celebrate the start of the magical holiday season at Holidays by the Sea in Falmouth! Whether you're singing carols at Nobska Lighthouse, greeting Santa as he arrives by boat at beautiful Falmouth Harbor, or running in the annual Jingle Jog, the holiday season in Falmouth is nothing short of spectacular!

The Holidays at Highfield

November 25th 11:00 a.m. - December 11th 5:00 p.m.

The Holidays are set for another year of spectacular decorating, seasonal activities, displays and Santa is expected to set up residence on specific days. The Gift Gallery will once again be alive with artisan gifts for all ages.

2019 Parade photo from the Cape Cod Chamber website.


Annual Lighting of Provincetown Lobster Pot Tree

November 26th, 5:30 p.m.

The Lighting of the Lobster Pot Tree, a Provincetown tradition that rings in the holiday season, is back for another year of holiday cheer!. Started in 2004 by artist Julian Popko, this "tree" is dedicated to recognizing the hard-working local lobstermen.


Sandwich Community Caroling

December 3rd, 7:00 p.m.

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.

Holly Days Stroll

December 11th, 12:00 p.m. - 4:00 p.m.

An afternoon of fun holiday festivities, merchant open houses, and a store decorating contest. Come and vote for the best holiday spirit!

Gardens Aglow photo selected from Heritage Museums and Gardens website.


Nantucket Annual Tree Lighting

November 25th, 4:00 p.m.

The Festival of Trees

December 2nd through December 30th 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 8th through the 11th

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

November 4th through the 25th

The Holiday Gift Showis 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 my position entails providing photography, video, and consultation services to vacation rental homeowners, and I have photographed over 700 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, visiting great coffee shops, and working with my community to support the schools and local events.