The Tisbury Street Fair’s reputation as a playground for silly-stringers held true again this year. Thin ribbons of fluorescent foam decorated the asphalt Monday night and no passer-by was safe.

The fair began in 1971 as a way to celebrate the town’s 300th birthday. It was founded by Cora Medeiros, often referred to as the unofficial town matriarch, who died in 2016.

It is unclear when the silly string tradition began but it was out in force again this year. Gabrielle Guimaraes stood on Main street with her cousin Melissa Yuman, whose thick curly hair was splattered bright pink and orange.

“The silly string is my favorite part,” Ms. Guimaraes said before she made it clear that she would only be spraying her family and friends.

Bubbles make everything fun. — Jonathan Fleischmann

Food is another mainstay of the fair. Lines for favorites, like malasada and fresh lobster rolls, were so long that it was hard to know where one started and another ended.

“I’ve had the mozzarella sticks and dried candy,” Ms. Guimaraes said. “I want to get the fried dough later.”

Charities and local businesses also lined the street and local musicians populated every corner.

Peter Shepardson, a resident of Vineyard Haven, sat at a table with his sister. Both were holding two black Labrador puppies in need of adopting from Angels Helping Animals.

Mr. Shepardson said events like the Tisbury Street Fair help promote local businesses.

Fire department knows how to make the burgers hot and smoky. — Jonathan Fleischmann

“It’s a venue to show [business] wares in a very public forum,” Mr. Shepardson said. “I’ve already bought a pair of shoes.”

Oak Bluffs restaurant Vineyard Caribbean Cuisine has had a booth at the street fair for five years. Head chef Newton Wait and his team chopped jerk chicken with razor-sharp precision before packing it with coleslaw for a line of hungry customers.

Mr. Wait said business at his brick-and-mortar locations is booming — he opened an additional store in Falmouth on July 4 — but he still counts the street fair as a very special day, as do his diehard fans.

“I have customers calling me from Jersey asking me if I’m going to be here because they’ll be in town,” he said. “A couple of them are here.”

Emily Burrows, owner of Vaalbara Supply in Edgartown, has been selling her handmade leather goods and other accessories at the fair for over 10 years. She said it’s the one time a year she is able to connect with some of her most loyal customers.

Businesses stayed open throughout the night. — Jonathan Fleischmann

“I always love seeing people I haven’t seen,” she said. “I do have people who wait to buy from me at this street fair, which is nice.”

Brian Gonsalves sat in between his son and mother while listening to the live music and finishing his last bites of barbecue. Mr. Gonsalves said he used to come to the fair when he was growing up in Vineyard Haven. His mother has lived in town for over 90 years and has been coming to the fair since she was a little girl.

He said the tradition means a lot to the community. “There’s something special about people being out on a summer night in a Vineyard town and seeing old friends and family.”