The sidewalks and parking spaces changed in Oak Bluffs this spring but among the things that stayed constant is the presence of Laughing Bear, the women’s clothing store that Annie Schwenk has owned and operated on Circuit avenue since 1985.

The store’s roots began in Woodstock, N.Y. Ms. Schwenk, who describes herself as “kind of a hippie from the old days,” moved there after studying French at Antioch College, living in France, working at Columbia University and as a nurse’s aide at Mass General Hospital in Boston, and six years of Manhattan life.

“I was a very free spirit,” she recalled with laughter during a recent interview with the Gazette. “It was the ‘70s and Woodstock was an artists’ community and a hippie world.”

In Woodstock, she and a friend learned the art of batik and made children’s clothing.

“We started using a coloring book with Native American designs like a bear,” Ms. Schwenk recalls when asked about the origin story of her store and its name. “We taught ourselves using those designs.”

By the time she left Woodstock, she was using non-toxic dyes and expanded the repertoire of images to unicorns, stars and moons printed onto nearly fluorescent-colored children’s clothing.

She joined her friends Arthur Smith and his wife Ellen on a visit to the Vineyard that involved camping in a thunderstorm. Despite that memorable but not pleasant experience, her feelings about the Island turned sunny.

“One thing I remember is that I loved Ocean Park,” she recalls. “It was kind of mystical. There was something about the spaciousness and the lawn going down to the sea. And for the past four years, since I moved into Oak Bluffs to live, I walk through Ocean Park every day. I say hello to the geese.”

Another of her first impressions has held fast over the years.

“I fell in love with the ferry,” she admits. “It’s like going through the clouds. It’s a passageway from one reality into another. I’ve always loved watching the ferry and the water.”

She brought her batik practice to the Vineyard and set up shop in Oak Bluffs. Laughing Bear has moved among three locations on Circuit avenue, first at the site of what used to be a Chinese restaurant next to the Army Navy store. A few years later, she and her batiking parter moved to a spot further up the avenue — but a year later, the town of Oak Bluffs condemned the building. Ms. Schwenk lost the money she had put into building renovations and had to shut down Laughing Bear and put all of its inventory and fixtures into storage temporarily.

She credits real estate agent Alan Schweikert with coming to her rescue. In 1990, he gave her the opportunity to rent 33 Circuit avenue, which had been the W.S. Brown Insurance office. With help from friends, Mr. Schweikert, and her mother, she bought the building. The space is one of Ms. Schwenk’s design: She had it renovated to put in the big front windows, create high ceilings, and add insulation.

By that time, Laughing Bear’s focus had to what it is known for: artsy, colorful, women’s clothing and unique pieces of jewelry. The store’s brightly colored dresses and tops, often stretched out on dowel rods to show their flow, catch the eyes and fancy of passersby.

“I am an artist. I think I have a pretty good sense of design,” Ms. Schwenk explains. “I have always looked for something a little bit more colorful. I also believe in showing your shape and flaunting it. I think you should say, ‘This is me and this is what I want to look like.’”

Laughing Bear customers are never far from her mind.

“The customers have helped us so much,” she says with fondness. “They’re all different shapes and sizes, so we ended up catering to every shape and size. We have a lot of clientele who come in here year after year. They’re Island people and summer people who end up loving the store and come back. We’re so lucky to have that.”

She also credits the longtime location she has held for so long on Circuit avenue.

“We’re close to the center. We’re right across the street from Reliable Market [and] the hardware store and we’re near the post office.”

Her location is one of the reasons why she has always chosen to keep Laughing Bear open during the winter months — that and wanting people to not be depressed as shops close at the end of the summer season.

Last year, Ms. Schwenk put the Laughing Bear building up for sale. Though she thought last season would be the store’s last season, she and manager Elaine Allen continue to be an anchor on the avenue and they’ll keep doing so.

The possibility of retirement makes Ms. Schwenk excited to think of the hobbies she’d have time to pursue: playing blues guitar, traveling, and making art are on her mind. So is what she accomplished by not pursuing playing the oboe as a career.

“Owning my own business has meant being able to determine my own life. It gave me freedom. And I don’t have to work for anyone else; I’m working for myself,” she said. “I know that’s a privilege.”

She is also reflective how much fun it has been to be on the Vineyard, to get to know her customers and her staff, and to now be living in the town that has for so long been her professional home.

“I think the town formed Laughing Bear. Oak Bluffs is the honky tonk town, the fun town. It’s where people are celebrating,” she said. “I just think Laughing Bear is this town. I don’t think it could have happened anywhere else.”