Judges Aoife Estes, Charlotte Hall, Willoe Maynard and Charlotte Benjamin stand outside the winning display at Mix. — Ray Ewing

A mechanical Santa wrote with a quill inside Moonstone Jewelers window, a mannequin fashioned a poinsettia dress in Alley Cat’s and a toy train zipped around photographs of snowy Vineyard days inside Island Art Gallery.

All were admired by the crowds assembled on Main street in Vineyard Haven on Tuesday, but Mix’s storefront — adorned with vintage toys stuffed in coffee cups — earned the best window award, given by four high school art students.

The lettered coffee cups spelled out Peace On Earth, and housed Pez dispensers, wind-up toys, Gumby and chattering teeth. A handmade sign by Paul Brisette, high school art department chair, will now hang in the window marking the store’s win.

“You could kind of walk by all the other windows,” said senior Charlotte Hall. “But this one stood out.”

The Green Room's window was filled with stars and lights. — Ray Ewing

The window contest kicked off Twelve Days of Tisbury, a nearly two-week-long holiday celebration that will bring a host of daily events to the town, said Beach House manager Jane Chandler, who has taken the reins for the Tisbury Business Association’s Christmas celebration.

“We haven’t had a window contest for years,” she said. “Some old traditions have been resurrected. Like Santa coming on the ferry; we did that when my kids were young.”

With the Christmas festivities, revival may be in store for the association, too.

In early November, TBA president Dawn Braasch announced she would be stepping down from her position, and would be forced to dissolve the association if no one came forward. So Ms. Chandler, who is not on the association’s board, offered to plan the town’s holiday celebrations.

Snow was the theme at Rainy Day. — Ray Ewing

“What will happen afterward remains to be seen,” said Ms. Chandler. “I think there is a possibility that if we restructure we can get some more involvement, and [the association] could continue and be stronger. I really hope that is what happens as a result of this.”

Ms. Chandler said she has been reaching out to other businesses the “old-fashioned way,” walking up and down Main street and State Road, and asking them to get involved with the Twelve Days of Tisbury events.

The efforts have paid off. For the first time this year, businesses have donated raffle baskets with proceeds going to the Family-to-Family program and raised $500 to give to the Vineyard Committee on Hunger.

Ms. Chandler said town businesses and schools have collaborated on a few other events. The high school theatre department will send out a slew of elves to Main street on Saturday, where they will hand out hundreds of gingerbread cookies baked by the high school culinary department. Tisbury school children will decorate the windows of Shirt Tales with drawings, and the businesses have donated $100 to give to an eighth grade student for outstanding community service.

Candles in the window at Midnight Farm. — Ray Ewing

The town will host its annual friends and family night on Friday with late shopping hours and sales until 8 p.m., and have brought Santa back for a 2 p.m. ferry ride on Sunday.

“It can be a wonderful thing to go downtown to any of your local stores and feel like you are part of something,” said Ms. Chandler. “To see Santa coming on the ferry or go on Fred Fisher’s hay ride, you don’t have to be five to enjoy that.”

She added: “I hope people enjoy this and see the value in keeping this tradition alive. Because it’s more than just the businesses, it’s about Main street. We need to do things together. I’m hoping there will be a rebirth in people’s interest in keeping businesses alive.”