- Saturday, December 7 at 10:00am to 1:00pm - Christmas Bazaar at American Legion Post 257 - Hosted by the American Legion Auxiliary. Baked goods, White Elephant tables, raffles including certificates to the Steamship Authority and the Cape Codder Group, door prizes and more.
- Saturday, December 7 at 10:00am to 12:00pm - Eggnog and Wreath Making at the Farm Institute - Rejoice in the spirit of the season with this festive class. Work together with evergreens foraged from the Trustees other Island properties to create a one of a kind wreath. All participants will take home their own wreath.
- Sunday, December 8 at 11:00am to 2:00pm - Holiday Hayrides - Enjoy a free holiday hayride in downtown Vineyard Haven, sponsored by the Vineyard Haven Business Association. Fred Fisher and sons will be in Vineyard Haven, driving their beautiful team.
- Dec. 12-15, 2019 - 38th Annual Christmas in Edgartown - Edgartow's Annual Holiday Celebration. See the lighting of the Edgartown Lighthouse on Friday, December 13th at 5:00 pm!
- Friday, December 13 at 10:00am to 5:00pm - Gifts of Art: An Island Art Show at the Carnegie - Come discover your next favorite work of art. Gifts of Art: An Island Art Show features new works by prominent Island artists Marston Clough, Deborah T. Colter, Margot Datz, Anna Lowell Finnerty, Julianna Healy, Colin Ruel, Jeanne Staples, Kate Taylor, Elizabeth Whelan and Wendy Weldon. Perfect for your home or as a special gift for a loved one, the small works in this select group show are sure to charm one and all. On display during Christmas in Edgartown and until Christmas Eve.
- Friday, December 13 at 8:00 pm - MVRHS Minnesingers Concerts at the Old Whaling Church - $15 per adult ~ Doors open at 7:30pm. Tickets available for purchase after Thanksgiving at THE CARNEGIE (Edgartown), ALLEY’S GENERAL STORE (West Tisbury), Leslie’s Pharmacy (Vineyard Haven) or Our Market (Oak Bluffs) or at the door. Please call 508-627-4440 with your questions.
- Saturday, December 14 at 9:00am to 3:00pm - Handmade from the Heart - A holiday season fundraiser to benefit Hospice of Martha's Vineyard. Come browse and buy unique, handmade items, including jewelry, needlepoint, knitted items, paintings, photographs, Christmas ornaments, baked goods and much more.
- Saturday, December 14 at 10:00am to 1:00pm - West Tisbury Farmers' Market - Indoor farmers market features locally grown produce and meat and locally made products. The market is dedicated to bringing local agricultural products to the people both living on and visiting the Island. The market was started in 1974 by a group of Island growers. That first year they had about a dozen farmers selling their produce.
- Saturday, December 21 at 10:00am to 4:00pm - Vineyard Artisans Holiday Festival - You won’t want to miss this very special holiday fair, our last of the year. Many holiday gifts are available, just right for that special someone who appreciates a true Island gift, and as usual always hand-made one by one.
- Sunday, December 22 at 4:00pm to 9:00pm - Opera Night at La Soffitta - Listen to the world's favorite arias and duets while enjoying the Vineyard's finest Italian cuisine. With Jenny Friedman, soprano; David Behnke, baritone; and Molly Sturges, keyboard.
- Daily in December at Ocean Park - Crosslands Annual Christmas Displays - Crosslands annual Christmas displays and light/music show.
- Tuesday, December 31 at 9:00pm to 1:00am - Roaring 20s Ball at the Portuguese-American Club - Dust off your flapper dresses or suspenders and wingtips and dance in 2020 with Joanne Cassidy and Mike Benjamin and their Big Band. Food, champagne toast, fire pit and more. Cash prizes for Best Dressed Couple, Best Flapper Gal, Best Dapper Dan and Best Dancing Couple as we kick off an old fashion dance contest on the dance floor.