In December 1981, a Vineyard Gazette headline proclaimed that churches and businesses in downtown Edgartown were working together on a new Christmas shopping program. Old Fashioned Christmas in Edgartown “interspers[ed] shopping with caroling, tree lighting and concerts,” one story reported.

The celebration came about after innkeeper Fred Hurley and Martha’s Vineyard Historical Preservation Society executive director Jane Tomassian had discussed how to bring the Christmas spirit back to town – and increase on-Island shopping. They took their thoughts to local business owners. The result was a promotional campaign for downtown in the off-season, but also a month of concerts, teas, special holiday decorations and abundant good cheer.

Shops outdo each other with creative window decorations. Jeanna Shepard

That celebration established one of the Island’s most anticipated annual events: Christmas in Edgartown. Mark your calendars for December 9-12. The Edgartown Board of Trade, which presents and manages the weekend, is encouraging all to enjoy the festivities, shop locally and support Island nonprofits.

Almost everyone who has lived on the Vineyard or visited in the off-season over the last 40 years has a favorite Christmas in Edgartown tradition or memory. The Teddy Bear Suite. Creative, colorful holiday light and plant displays installed by Donaroma’s. The parade down Main street, with Santa arriving in a fire truck. Lighting the Edgartown Lighthouse. Many people cite the Minnesingers’ holiday concert as their favorite.

Traditions of years past remain vibrant memories. Julia Tarka, owner of Rosewater Market and vice president at the Edgartown Board of Trade, recalls the Fligors store on North Water street as having the best holiday decorations she has ever seen. Janice Wooden at Past and Presents chaired Christmas in Edgartown for six years and recalls tours of homes and inns, the Hob Knob’s train display and the live kittens that her own shop displayed in their windows, along with their own doll beds. Janice also remembers when the parade had only three entries, and laughs with delight to think of how big the event has become.

Walking around town at a night is a treat. Jeanna Shepard

Since the inception of Christmas in Edgartown, some traditions have become firmly entrenched and others have waned as their owners or public tastes moved on. But the primary roots remain the same: drawing people together into Edgartown’s historic downtown to share holiday cheer, encouraging on-Island spending to support local businesses and raising money for local nonprofits.

What started as a few civic-minded Edgartowners going door-to-door to encourage fellow shopkeepers to donate to local causes has grown to an ability to donate more than $100,000 in just one year. The weekend is a crucial component of many Island nonprofit budgets; organizations hold fundraising events or partner with businesses on end-of-year campaigns.

The businesses are encouraged to participate within their own capacity. For some, that means big events requiring a large corps of volunteers; for others, it might mean partnering with a nonprofit to set up a wrapping station from which money paid for the service goes to the organization rather than the business.

The Edgartown Light will come alive with color again this year on Friday, December 10. Mark Alan Lovewell

The dollars raised go to causes varying from Hospice, which partners with Vineyard Trust on the Handmade from the Heart craft fair; animal shelters supported by Past and Presents through its Shopping Night for Men; and the Red Stocking Fund, which for years presented the much-loved Great Chowder Contest. The Minnesingers concert at the Old Whaling Church – a longtime staple on the schedule – is a joyous showcase of talent that also raises funds for the group’s biannual European musical tours. 2021 marks the 11th year that Point B Realty is working with the Martha’s Vineyard Boys and Girls Club by donating money from the Teddy Bear Suite (now a scavenger hunt) and 5K Teddy Bear Trot. The money supports Healthy Happy Kids, a food scarcity initiative feeding the Island’s children.

Edgartown Board of Trade president Erin Ready notes, “There are so many examples of how our businesses open their doors and make sure that the causes and initiatives on the Island get exposure throughout the weekend. It’s a great way to get involved and fundraise for the causes that everyone on the Island really cares about. We try to bring the good will into focus: raising money for local non-profits brings more meaning behind the weekend festival. It goes to show how engrained the Edgartown business community is with so many of these efforts.” Responsibility for paying for decorations, events and staffing falls to the merchants and owners themselves. The board of trade itself relies on membership dues as well as half of the proceeds from The Great Edgartown Raffle, its annual 50/50 raffle. Money earned is split between the raffle winner and the board of trade. Erin is also cognizant of the impact that the weekend has on local artists, who people often forget are independent businesses themselves. Christmas in Edgartown, as well as holiday fairs Islandwide (see p. 23), offer opportunities to purchase items made by local artists.

After the 2020 celebration was “magically modified” to follow Covid-related guidelines, business owners, Island residents and visitors alike are eager for Christmas in Edgartown’s return. Shop owners are brainstorming about decorations and window displays. Vineyard Trust executive director Nevette Previd is working with John C. Anderson’s painting company to complete some restoration work at the Old Whaling Church so that audiences can enjoy its beauty. Safety continues to be a focus and the board of trade is working with the town’s government agencies to ensure guidelines are followed.

Santa's got the parade covered on Saturday morning. Maria Thibodeau

Everyone involved is eager to make magic and bring back a bit of normalcy, especially for children on the Island. Point B Realty managing director Guinevere Cramer finds the festival offers an opportunity to be reminded of how lucky Island residents and visitors are. “We’re on this gorgeous island, with friends and family,” she points out. “It’s just really a magical place to celebrate the holiday season.”

Elizabeth Bennett is an editor and journalist working for the Vineyard Gazette.

Editor's Note: For up-to-date information on Christmas in Edgartown events and times, visit