Andy Herr and Gabriella Greco sat in a small alcove outside of Bananas Clothing on Main street, Vineyard Haven. There was a guitar case open at their feet with a few crumpled bills inside. Andy strummed while Gabriella sang. People strolling by turned their heads to look, one stopped to listen. Several shops down, in front of Bunch of Grapes, a duo of fiddlers played. Further down the block Merrily Fenner and Christine McLean from the group Serendipity performed near the Capawock theatre. As their song finished a young couple standing at the refreshments window of the movie theatre ordered a medium popcorn before going to see the new film Me Before You.

Alyssa Cimeno tries her hand at busking. — Mark Lovewell

It was 6 p.m. on a Saturday evening. Shops were still open and would be for another hour as people enjoyed the evening in town — browsing, buying and eating — during what has become a weekly event this summer, the Saturday Stroll.

Saturday Stroll is a cooperative effort between the Tisbury Business Association, the Vineyard Haven Harbor Cultural District and the Chamber of Commerce to bring more people into downtown Vineyard Haven. It’s a group of citizens and business owners dedicated to a vision of Vineyard Haven as more than a bus stop on the way to Oak Bluffs or Edgartown.

Main street has had its ups and downs. A massive fire in 2008 displaced two integral businesses, Bunch of Grapes and Cafe Moxie. Both rebuilt, but Cafe Moxie closed in 2014, replaced by Mad Martha’s Ice Cream. Business associations came together and fell apart. Tristan Israel, long time selectman, said that about a decade ago the town did a report of Main street, taking stock and upgrading the street. He remembered going into enough detail to compare textures of pavement.

“Main street looks very different from 20 years ago,” Mr. Israel said, leaning out of the window of his truck. “It’s certainly more vibrant, but I think it’s time to look at this stuff again.”

Vineyard Haven library director Amy Ryan and Vineyard Playhouse executive director MJ Bruder Munafo. — Mark Lovewell

Downtown Vineyard Haven is known for its year-round businesses, many of which remain open 11 if not 12 months of the year. For many business owners, the idea of increasing the vibrancy of the area began over the winter holidays. First they started organizing sales at various stores to take place on the same day. Then they began a more concentrated effort to host events like Thursday Friends and Family Night. As the winter thawed, the group started to talk more seriously and decided they were ready to commit to an association again.

Sarah York, general manager of CB Stark which is celebrating its 50th year and is one of the business mainstays on Main street, was involved in the last association and is president of the current one.

“Vineyard Haven is tricky, the challenges that restaurants have in keeping night business here,” she said. “I think we have great restaurants that do their best with what they’re given, but this isn’t a town full of restaurants so our nightlife is never going to be like Edgartown or Oak Bluffs. Doing something like this, where we can at least have entertainment and something going on, maybe someone could head over to Edgartown for dinner at seven, but at least they could be in Vineyard Haven from five to seven.”

Enhancing the dynamic of the street won’t happen over night, Ms. York admits, and it can be difficult for business owners who already invest so much time in their shops to set aside more time for association meetings and extra hours of operation. But Vineyard Haven has a fan section and they are dedicated.

“Eighty per cent, 90 per cent of these businesses are open year-round,” Ms. York said. “Edgartown closes up. Oak Bluffs closes up. These are businesses that if you need something in February, the Green Room is open, Rainy Day is open, we’re open, LeRoux is open, you go up and down Main street, Brickman’s is open. We’re open, we’re here and that’s pretty huge.”

Tara Lewis of Mangku food truck, a new Main street venture, talks with a passer-by. — Mark Lovewell

One of Vineyard Haven’s biggest struggles is the small restaurant scene. It is not a hub of dining and cannot compete with the bars in Oak Bluffs and Edgartown. Currently restaurants in Vineyard Haven can get a beer and wine license and a recent vote expanded the license to include hard liquor, but no bars are allowed.

But for Robert Cropper, the manager of Juliska, Vineyard Haven is growing in its own right.

“It’s my favorite town,” he said, standing behind the counter as people browsed shelves of dinnerware. “It’s a great mix of people and stores and it doesn’t get as jammed. It’s more comfortable.”

Mr. Cropper sees downtown Vineyard Haven as filling a niche on the Island.

“You can go to Edgartown for clothing, here it’s home goods,” he said. Juliska is joined in this arena by Scott Mullin’s Brickyard, LeRoux at Home, Rainy Day, Bespoke Abode, Midnight Farm and more.

Hubs are helpful for business, Sarka Havlatkova Greene, owner of the spa Revive by Sarka, agrees. The more options, the more likely people will come, but she also thinks outdoor seating would go a long way in helping business boom.

The Sound Wave: Gabe, Curtis, Jared, Christian, Oliver, and Jake. — Mark Lovewell

“It amazes me, we have hardly any places to sit outside to have a cup of tea or a glass of wine,” she said.

And yet there are nooks and crannies on the street if you know where to look. One nook in particular is Nat’s Nook, which opened in the summer of 2014 and has a delightful patio down a small alleyway where customers can sip tea and eat crepes.

A new food truck recently set up shop next to the Capawock Theatre and also has a small outdoor seating area. Mangku Truck serves rice bowls topped with pickled vegetables, Island meats and an egg. The low orange chairs scattered around the truck were nearly full on a recent Friday afternoon as people waited for their bowls, finished a dessert of whole orange sorbet or just rested a moment while reading the menu.

“I want there to be more business on Main street and I want to be a part of it,” said Jacqueline Foster about her new food truck.

In front of Bernie’s and Bobby B’s (pizza and ice cream), Bob and Jeannette Breth have created a brick courtyard with blue picnic tables, umbrellas and patio lights.

Soon to be ninth grader Violet Southwick performs for strollers. — Mark Lovewell

“It feels like there is a heartbeat in town,” Mr. Breth said of the emerging changes in town. The Breths have become mini Vineyard Haven moguls. Last summer they opened Bernie’s Homemade Ice Cream and now have taken over Bob’s Pizza next door, giving the whole space a makeover in the winter months. They have also taken the reigns at Tisberry Frozen Yogurt and are opening Candy Haven down on Union Street. Mr. Breth said he feels strongly about developing more businesses in Vineyard Haven because of the people.

“The people you meet here, they aren’t just in and out,” he said. “You can have a conversation with them, make a personal connection.”

It was generally agreed that it will take a combination of changes and time to help Main street reach its full potential. The street’s gala night may be the annual street fair, this year on July 8, but businesses in town are looking for something more than one night.

Judy Hartford the owner of Bananas Clothing said it will come in steps.

“I think the more there is, the more opportunities there are for people to eat, talk, have a glass of wine, the better,” she said.

“We want to be here,” Ms. Hartford added. “That’s the main thing.”