Evergreens adorned with twinkling lights, fragrant pine wreaths and festive shop window displays on Edgartown’s Main street are a sure sign of only one thing: Christmas in Edgartown has arrived. 

This weekend, the town will awaken from its off-season slumber to welcome Islanders and tourists of all ages to the 42nd annual Christmas in Edgartown festival, complete with a parade featuring Santa himself, a variety of sweet treats, live music performances and artisan markets, among other holiday happenings. 

The festivities kick off Thursday, Dec. 7 and run through Sunday, Dec. 10. Dozens of Island businesses and organizations will host, sponsor or run events, said Erin Ready, executive director of the Edgartown board of trade, which manages the festival. 

Iva Ivanova preps the Black Dog for the holidays. — Ray Ewing

Ms. Ready and board of trade president Julia Tarka worked with a committee of about 20 volunteers to coordinate the weekend. As soon as the town’s summer scene ends in September, the holiday team starts planning the festival. This year, its lineup is full of both new activities and returning family favorites. 

Making a comeback after its successful 2022 debut, and one of Ms. Ready’s personal Christmas in Edgartown must-dos, is the Holiday Faire in the Edgartown Village Green. Hosted by the Edgartown Village Market, which launched in the summer, the fair will feature retail products from more than 20 local artists, a variety of food and beverages and musical accompaniment. It runs from 10 a.m. to 3 p.m. on Saturday.

The idea for the faire came from Sea Legs boutique owner Grace Romanowsky, who said that after a summer of running the weekly Edgartown Village Market, she was ready to make the European-inspired Christmas market even bigger in its second year. 

“There’s definitely more production surrounding it this year,” she said. “We’re doing a big tent rental… and we’ve got these gorgeous, long farmhouse tables, heating and even more vendor offerings and concessions.”

Festival-goers have another opportunity to peruse Island-made goods on Sunday from 10 a.m. to 3 p.m. at the new Artists in Residence market in the Faraway Hotel. Inspired by the book Vineyard Folk: Creative People and Places of Martha’s Vineyard by Amanda Benchley and Islander Tamara Weiss, the market will highlight the art of seven Vineyard jewelers, painters, potters and seamstresses. 

The former Kelley House reopened as Faraway over the summer after a year and a half-long renovation. Regional general manager MarcAnthony Crimi said that he had been searching for a way to reconnect the hotel to its Island community when he stumbled upon Vineyard Folk in a local shop in August.

Mr. and Mrs. Claus are ready for the holiday. — Ray Ewing

“I fell in love with it and ended up buying a bunch to use as VIP amenities for our hotel guests,” said Mr. Crimi. “Then, I started reaching out to some of the artists to gauge their interest in [the market] and they were all so excited. I think this will really anchor our space over Christmas in Edgartown.”

Island artists are not the only ones taking over the Faraway Hotel this weekend. 

Fully indoors and bigger than ever after three years of pandemic-induced modifications, the Teddy Bear Suite returns and will fill three of the hotel’s suites with thousands of stuffed bears modeling holiday-themed vignettes. 

“We’ve got bears of all sizes, from literally six feet tall to six inches,” said Win Baker, vice president of operations at Point B Realty, which runs the event. “We really went on a buying blitz when we first started the suite, then people started donating [teddy bears] to us… and now people acknowledge us as one of the largest collections on the East Coast.”

Available for snuggling and photo shoots, the bears have drawn thousands of visitors in their 13-year history on display and more than $400,000 in donations to the event’s non-profit partner, the Martha’s Vineyard Boys & Girls Club. 

Festival attendees can visit the teddy bears all weekend long and make donations to the Boys & Girls Club at the door or online at the Teddy Bear Suite website, said Mr. Baker. 

“The fundraiser targets specifically their after-school food programs that serve hundreds of families on the Island,” said Mr. Baker. “If you can donate, that’s great. But if you can’t, that’s okay too. The bears are for everyone.” 

Win Baker and Wendy Harman snuggle up with some of the bears at the Teddy Bear Suite. — Ray Ewing

For those looking to spend some time outdoors this weekend, a shuttle awaits just off the Chappaquiddick ferry dock to take passengers to Illuminate Mytoi, an LED candle-lit stroll through the island’s Japanese-style garden, running 4 p.m. to 6:30 p.m. Saturday.  Online registration for the event is required.

Snow may not be in the forecast, but Caroline Drogin, Islands engagement manager of The Trustees of Reservations, which owns the garden, said that this new Christmas in Edgartown event will transport wanderers to a winter wonderland.

“We’re stuffing candles inside of about 200 to 250 bags and lining the paths,” said Ms. Drogin. “It’s an opportunity for folks to take a second away from the hustle and bustle of downtown Edgartown and have a meditative stroll to think about what they want to leave behind in 2023 and embrace in the new year.”

Nature lovers can also connect with wildlife at a more unexpected location on Saturday. Just beyond the clothing racks at Boneyard Surf Company will be exhibits of animal skeletons, pelts, pellets and even a live snake and turtle for the Felix Neck pop-up natural history museum from 11 a.m. to 2 p.m.

The museum will showcase a variety of information about Island critters, focusing on how each one survives chilly New England winters, said Mass Audubon islands education manager Josey Kirkland. 

“It’s a way for us to just remind folks of all ages to take time out of consumerism and engage with the natural world around us,” said Ms. Kirkland. 

For a complete schedule of events at the 2023 Christmas in Edgartown festival, visit christmasinedgartown.com.