Threads of neon colored Silly String were already strewn across Main street as vendors put the finishing touches on their booths for the Tisbury Stree Fair.
The celebration took place Wednesday evening in Vineyard Haven, crowding the pavement with fragrant food stations, clothing displays and artwork.
This year marked the 55th anniversary of the Tisbury Street Fair, an event launched in 1971 by former town select board member Cora Medeiros. Though it began as a celebration of the town’s 300th birthday, the fair has grown into a beloved community gathering and unofficial start to the Vineyard’s busy season.
Ross Hathaway looked back fondly on childhood summers spent causing chaos at the fair.
“One of my favorite things to do as a little kid was trying to run through the crowd as fast as possible without knocking into anyone,” he said. “Me and my friends would try to race to the end.”
He also remembered the dunk tank station, where kids used to take a plunge on hot evenings.
This summer, Mr. Hathaway manned the Attic’s taco station. He described the 24-hour process of marinating the chicken and shrimp, pausing a few times to hand a customer a taco.
A few booths down, Ria Cimeno and her granddaughter Luna Harre reminisced about their family’s long history with the fair.
“We’ve been going to the Tisbury Street Fair since her mother was in a pack on my back, over 50 years ago,” she said, pointing to Ms. Harre.
Although they have attended the fair for decades, this was their first time vending. The pair started crafting together this past year, pasting printed designs on the insides of seashells for Ria’s business: She Sells Seashells by the Seashore Handmade by Ria on Martha’s Vineyard Island.
Ms. Cimeno said the process includes finding the shells, washing them, bleaching them and letting them dry out. From there, she cuts out eye-catching designs from rice paper, napkins or stickers, and uses Mod Podge and resin to stick them on.
If the shell has to be sanded first, she said, the final product takes “one and a half songs to make.”
Ms. Harre said the Tisbury Street Fair means a lot to the community.
“People love when they see the sign come up,” she said. “We are in the thick of summer.”
One relatively new vendor sat at the corner of Union street, putting money into his red plastic cash register and sipping a milkshake delivered by his mom. Grayson, age 11, was selling inflatable animals for the third year in a row. He said he anticipated the inflatable gummy bear would be the most popular sale of the night, but his favorite was the alien.
Grayson said the best part of the street fair is “just really having fun and selling with my own business.”
Many young vendors took the lead at this year’s street fair, including the troupe at Theatre on the Blue. The company, started by Heather Capece, was fundraising for their trip to the Edinburgh Fringe Festival in Scotland, where they will perform their rendition of The Hobbit.
Isla and Nicola, two teenagers in the group, took turns holding a microphone to convince passersby to get hair tinsel in support of the cause. They said their favorite part of the market was being able to spread the word about their upcoming performance.
“It’s really cool to support local theatre, and I think people should do it a lot more,” Isla said.
Down the road, people listened to live music performed by Dave Willis and the Down Island Band. Mr. Willis, the singer songwriter, said this was the group’s fourth year in a row performing at the street fair.
Cary Steinberg and Philippe Jordi walked by holding ice cream from the Mad Martha’s street cart. Mr. Jordi said other than the ice cream, the live music is the best part. “Tisbury is kind of a quintessential small town in New England…it’s probably a little bit more local than some of the other events,” Mr. Jordi said.
After moving to the Vineyard from Ireland, painter Joan Walsh has been selling her art at the street fair since 1995. Ms. Walsh said she aims to bring joy to people through her art, and that the street fair — and Martha’s Vineyard — is the perfect place to do that.
“It’s hard to say what it is,” she said. “It’s je ne sais quoi — it’s very peaceful…you meet people from all over the world.”
This article appears in July 10, 2026.