Christmas in Edgartown started 40 years ago as an antidote for a town with a dearth of holiday cheer.

Main street shops are all decked out for the holiday. — Ray Ewing

“It’s to get the spirit back in town, which is sorely needed,” Jane Tomassian, then-executive director of the Martha’s Vineyard Historical Preservation Society, told the Gazette in 1981.

Over the years since then the town has shaken its holiday enthusiasm deficiency. Today, small Christmas trees with colorful lights dot Main street, garlands and wreaths decorate store-front windows and front doors, and for four days this weekend the town will be a magnet once again for all things Christmas, as it has for four decades.

“Each year we see more and more people excited and looking forward to getting involved,” said Erin Ready, executive director of the Edgartown Board of Trade. “Everyone contributes a little bit, which is spectacular. I think we’ve become more organized and with that have drawn more support across the Island.”

The 40th annual Christmas in Edgartown celebration takes place from Dec. 9 to Dec. 12. The weekend kicked off Thursday evening with Late Night Lights on Main street, where businesses stayed open after hours and Backwater Trading Co. hosted an open house.

Tonight, the traditional lighting of the Edgartown Lighthouse takes place at exactly 6 p.m., and on Saturday at 11 a.m. the parade returns to Main street after a year off due to the pandemic.

“As I’ve been saying, it’s the best parade of 2021, which [is] easy because it will be the only parade,” Ms. Ready said.

Aubrey Ashmun hangs greens with care at One North Water Street. — Ray Ewing

The Rise dancers will lead the procession and Santa will bring up the rear. Along the way watch out for fire trucks, snowmen, elves and fishermen tossing Swedish Fish from the Striped Bass and Bluefish Derby float.

“We’re just really excited to have it again. It was a bummer last year that it was canceled,” said parade organizer Leah Fraumeni. “I know people look forward to it and it’s just bringing back that Christmas cheer.”

As always, the parade will happen regardless of the weather, Ms. Fraumeni said.

“I’ve had it when it was in the single digits. It’s been absolutely down pouring before. And then there’s been times when we were in T-shirts, it was so warm out . . . Even when it was pouring rain, people still lined up, which was amazing to see and to hear, that people were so excited to see it,” she said.

Then, as now, the goal of the weekend is also to bring business to local merchants.

“Shopping in Edgartown during the holiday season is far removed from the noise, crowds, and frantic pace found elsewhere,” reads a brochure for the inaugural event and is echoed by business owners today.

Vineyard Square hotel is wrapped and ready to receive. — Ray Ewing

“It’s also just a great opportunity for shopkeepers to really have a last hurrah with big sales and big festive energy,” said Julia Tarka, the current president of the Edgartown Board of Trade.

Covid is still a concern, especially as cases have been rising on the Island. But since many of the events take place outdoors, the festivities have the green light.

“So much of Christmas [in Edgartown], because you’re already outside, is pandemic friendly in that sense,” Ms. Tarka said. “You’re outside to enjoy the light show at Donaroma’s and you’re outside to enjoy a parade, so I think we

have confidence that, in working with the Edgartown Board of Health, those events will be able to happen safely this year.”

The Minnesingers will return to the Old Whaling Church, with shows on Friday at 8 p.m. and Saturday at 4 p.m. But the group will not process through the church, have a sing-along with the crowd or invite alumni to join the finale due to pandemic caution, director Abigail Chandler said.

“Even with the restrictions, and a little bit pared down, it’s really going to be special to be back in that space,” Ms. Chandler said.

Other event hallmarks have also had to shape-shift. Point B Realty will do a teddy bear scavenger hunt in lieu of decking out a suite with stuffed bears at the Harbor View Hotel or in Nevin Square.

Peter Palandri and Grace Romanowsky deck the yard at Sea Legs. — Ray Ewing

“The joy that these kids get after accomplishing something . . . it’s really moving and a lot of fun . . . it’s pretty dang cute,” said Guinevere Cramer, who helps organize the Teddy Bear Suite.

Even if the event is different, the goal — raising money for the Boys and Girls Club — is the same, Ms. Cramer said.

“It’s more than just [a] fun and fuzzy [event] . . . being a cornerstone event for Christmas in Edgartown,” she said. “It really is a fundraiser that yields a substantial result and funds a vital program on the Island.”

Since its inception in 2010, the teddy bears have raised nearly $300,000 for the Boys and Girls Club.

Christmas in Edgartown is also about neighbors and friends coming together to celebrate another holiday season, Ms. Ready said.

“A lot of people form traditions around it, too, which is nice,” she said. “Whether it’s dinner at the Harbor View or Alchemy or hot chocolate and cookie making, there are definitely highlights that people come back to Edgartown for year after year.”

For a full schedule of events, visit