Edgartown is all aglow with pine swirling up the street lamps and doorways decked with mistletoe. The twinkling lights in storefronts signal that the 44th annual Christmas in Edgartown has arrived. 

The weekend’s festivities make up the largest event of the winter season and the parade is the crown jewel. Santa himself will march down Main street alongside a plethora of Island organizations starting Saturday at 11 a.m.

Teddy bear suite is ready for visitors.

Ray Ewing

Teddy bear suite is ready for visitors.

Ray Ewing

Ahead of the parade this week, the groups behind the floats made their final touches. Inside the Martha’s Vineyard Boys & Girls Club on Wednesday, a gaggle of fourth graders discussed what clothes they own that have the most pockets to stuff candy in during the parade. 

“I had one of those cargo pants with all the folding pockets that were baggy,” remembered Finn Welch from last year’s parade. “So when I put the candy in it looked normal and the people didn’t know.” 

His friends Brooklyn Cancellare and Asher Bedo schemed as well, and theorized who in the club would throw Jolly Ranchers furthest into the parade crowd. 

A crucial part of their outfits. they said, is yellow face paint to match the Boys & Girls Club float, which is themed around the movie Despicable Me’s minions. 

The town and business owners have been preparing for the event the last several weeks. Shopkeepers are bracing to welcome visitors through their doors and the only part of their shops left undecorated are the floors. 

Atop the Nell Home storefront is a giant gingerbread man tipping his hat to townsfolk visiting Main street. The windows of Claudia’s jewelry shop are frosted with pine and golden leaves, resembling the necklaces inside. 

Rockfish is bedecked with strings of ornaments and a giant nutcracker welcoming guests through the front door. The Newes also has its festive outfit on, with a Christmas tree resting beside its wood-burning fireplace. 

The Boys and Girls Club prepares its minion-themed parade float.

Ray Ewing

The Boys and Girls Club prepares its minion-themed parade float.

Ray Ewing

Erin Ready, the Edgartown Board of Trade’s executive director, said the weekend started in 1981 to entice sales during the off-season.

“It was literally a couple of shopkeepers trying to get a couple visitors in the dead of winter,” Ms. Ready said. “That history has stayed true to the mission behind all of this.”

Aside from the parade, the town has yuletide-themed events throughout the weekend. 

After the procession, kids and their families can get warm inside the Edgartown Library which is hosting a make your own wrapping paper craft session. Children’s librarian Elyce Retmier said each year the library has homemade crafts because the creations often become holiday heirlooms for families. 

“I’ve always liked to do crafts that are personal, like an ornament they can look at each year and remember when they were three,” Ms. Retmeir said. 

The Edgartown School’s 32nd Annual Arts and Crafts Festival this year will be held on both Saturday and Sunday from 10 a.m. to 2 p.m. with food concessions provided by the 8th grade class. Paradegoers can enjoy food and drink at the Holiday Faire at the Edgartown Village Green, which will host more than 30 local vendors Saturday from 10 a.m. to 3 p.m.

Inside the Carnegie, a miniature town similar to Edgartown celebrates Christmas. Debbie and Dave Brown present their Dickens Christmas Village, complete with more than a hundred miniature pieces of candlelit homes, trees and townsfolk, some of whom are ice skating.

“I think what’s great about Debbie and Dave Brown is that they’re so proud of their collection,” said Sissy Biggers, community engagement director of the museum. “Anyone who’s a passionate collector wants their collection to be shown. That’s the joy I think they get in it.”

Businesses decorate for the big weekend.

Ray Ewing

Businesses decorate for the big weekend.

Ray Ewing

Even animals are getting in on the holiday cheer.

The horses of Sunnyside Rides are currently resting at a barn in West Tisbury before a busy weekend pulling guests in their maroon carriage. Co-owner Laura Marshard said the rides, which depart from the Harbor View Hotel, are already sold out.

But steeds Dudley, Tim and Touch of Texas (named for the Texas shaped spot on his forelock) put on a show for anyone while trotting through the town. She said the horses aren’t camera shy.

“They have sleigh bells on them and the carriage is decorated,” Ms. Marshard said. “It just adds to the feel good festivity.”

On Sunday at 11 a.m. a costume dog show will commence at the pocket park on Main street. The event, along with a pet stocking sale on Saturday at Past & Presents, will raise funds for the furry friends inside the Animal Shelter of Martha’s Vineyard.

Teddy Bears are getting their beauty sleep and grooming their fur to be extra snuggly for when kids come to play inside the Harbor View Hotel. The Teddy Bear suite event is a fundraiser for the Boys & Girls Club and ticketed this year.

Wendy Harman, owner of Point B Reality, which throws the event, said teddy bears as big as six feet tall and as small as three inches are having a grand time in their hotel room. Some are playing the piano and others are having a pool party in the bathroom sink. 

“We’ve got musical teddies, we’ve got spa teddies, we’ve got holiday teddies and we’ve got angel teddies,” Ms. Harman said. 

The town’s worship communities also have many events prepped. 

At Saint Andrews Episcopal Church, Christmas in Edgartown is a long celebrated tradition since the wife of a former rector helped found it, said church secretary Heather Anne Slayton.

For the past 17 years the church has been celebrating with meatballs. The church will provide over 500 of them on Saturday for free to community members. At the event, children will write more than a hundred Christmas cards that get sent to Veterans Affairs hospitals to accompany their breakfast trays on Christmas morning.

“The kids as young as six months are scribbling on them,” Ms. Slayton said. 

The first night of Hanukkah menorah lighting extravaganza will take place at Main street pocket park on Sunday at 4 p.m.

The Federated Church of Martha’s Vineyard’s bells ring with Christmas music each morning. It has a slew of events scheduled for the weekend with its Habitat for Humanity of Martha’s Vineyard fundraiser returning. Titled No Room in the Inn, the display shows roughly 70 nativity scenes.

Pastor Mark Winters at the Federated Church said it can be difficult to feel the spirit of Christmas this year, with all the challenges the world faces. But he said God is with everyone no matter where they are in life and coming together can help provide comfort. 

“I encourage people to find something that meets their spiritual needs and go participate and be present,” Reverend Winters said. “We all need community.”