Tisbury celebrates annual Street Fair

Annual celebration highlights Vineyard Haven businesses, the community, and the founding of the town.


Monday evening marked the annual Tisbury Street Fair and Tisbury’s birthday, with crowds and tables winding up Main Street, many of which represented new small businesses.

Tisbury was officially incorporated as a town back in 1671, though the fair began in 1971. It was founded by Cora Medeiros, previous Tisbury select woman who died in 2016, as a way to celebrate the town’s 300th birthday.

The community gathered around 6:30 pm Monday for the festivities, including live music, lobster rolls, face painting, cotton candy, and lots of laughter. Children chased one another up and down the street, and customers browsed vendors’ pop-up tables lining the sidewalk.

By close to 7 pm, the street became tightly packed with people. Some of the more popular booths had lines across the pavement. Good Shepherd Parish was among the busier tables, with at least 20 people lined up for malasadas fried by church volunteers.

“It’s really exciting,” said Mark Clements, one of the volunteers. “They give us tubs and a recipe and say, ‘Please make some dough at your house,’ so everybody makes it. And then early afternoon on Monday, the ladies chop it up and bring it down here.”

Their operation included an assembly line of people passing each other dough, frying it, and finally selling the finished product. And they’ve been doing this at the fair for four years now, said Clements.

A few tables down from Good Shepherd Parish was Cameron Bishop, with her family’s small business called Sideline. Her mother opened the apparel and accessory collection on Main Street back in 2020, with inspiration from Bishop’s brother.

The aim of the collection is to produce and sell accessories and clothing inspired by sports game days, with Bishop herself in dance and her brother a football player throughout high school and college.

Another small business down the road, Adrift, has been selling clothing through pop-ups for some time, but only just began at the fair this year.

“We finally got our own brick-and-mortar storefront in May, which is really exciting,” said Alysha Norbury about her store.

The end of the street held another popular table, the American Legion’s lobster rolls. The women running the table wore T shirts that read “Lobster Ladies,” handing out bags to customers with a smile.

Nancy Nevin, one of the ladies, said they do lobster rolls at the American Legion in Tisbury every Tuesday, and have been at the fair for as long as she can remember. She recounted when Medeiros began the street fair years ago.

By a little after 9:30 pm, the street quieted, with people dispersing throughout the course of the fair, anticipating its return next year.