Downtown Vineyard Haven’s monthly First Friday event ballooned into a three-day Christmas party over the weekend, complete with two tree lightings and two visits from Santa Claus.

“Tis the Season” festivities kicked off Friday afternoon at the Martha’s Vineyard Museum, which waived admission fees from 4 p.m. to 6 p.m. so that all comers could enjoy hot cocoa and snacks, a snowflake scavenger hunt, cardboard gingerbread house building and live music.

As dusk fell, the museum switched on its Christmas “tree,” a cone of lights strung from the landmark flagpole overlooking Lagoon Pond.

After dark, the action moved to Main street, where shops stayed open late and the street was closed from Cromwell Lane to Union street.

Holiday market is set up in the Capawock. — Jonathan Fleischmann

Wood fires crackled in open fire pits with benches for sitting by the flames, and propane-heated obelisks provided extra warmth on the weekend’s coldest night.

“This is some hard-core Yankee [stuff],” said local musician Jim Moore as he joined a circle of folks around the fire.

Decked in Santa hats and smiles, cultural district president Althea Freeman-Miller and board member Taylor Stone poured hot cocoa and made sure plenty of marshmallows were speared on long toasting sticks, ready to be made into s’mores with chocolate bars and Graham crackers.

Festooned with holiday lights, the vacant former Bowl and Board retail building became the stage for an energetic performance by the Jaywalkers, whose eclectic mix of up-tempo oldies had Ms. Freeman-Miller and others dancing in the street.

There was music indoors as well, just across the street at S & S Kitchenette, where singer-songwriter Jared Salvatore’s solo performance was followed by a set from the group Big Weather.

On Saturday, Union street closed for an outdoor art market with 18 local vendors, while MVY jazz host Dave Kish spun records at the intersection with Main street.

The jollity was so infectious that a caroling group of unknown origin joined in, Ms. Stone told the Gazette Sunday.

“I caught them at Linden Tree Park. They were just singing,” she said with a smile.

For kids, Saturday’s holiday fun centered around the Black Dog campus on Water street, where Santa Claus held court in the tavern amid cookie-making, ornament-decorating and s’mores-making activities.

Mr. Claus also lighted the restaurant’s Giving Tree, decked with ornaments that each represent a donation to an Island cause.

On Sunday, Mr. Claus was back in town, arriving by Tisbury fire engine as gentle flurries fell from snow machines above. 

This time, the Christmas patriarch welcomed visitors to his workshop on the deck at Main Street restaurant Fish.

“That was a big hit,” said Elaine Barse, owner of the Green Room stores and president of the Vineyard Haven Business Association, which teams up with the cultural district for First Friday and holiday events.

Another popular offering Sunday: free wagon rides behind Fred Fisher’s draft horses, whose hoofbeats rang out along Main street as the snow machines sifted down their flakes.

Local businesses have chipped in to make the wagon rides free of charge, Ms. Barse said.

“We want everything to be free for everybody,” she said.

Wagon rides, caroling, Mr. Claus and his workshop all will return on Dec. 22, when downtown Vineyard Haven once again hosts its Winter Wonderland from noon to 2 p.m.