Holly Alaimo describes the creation of the Arts District

Holly Alaimo. — Photo courtesy of Holly Alaimo

Holly Alaimo is a busy woman. Once a painter, a waitress, a seamstress in the wardrobe department of the Boston Ballet, and well-known as the former owner of Dragonfly Gallery, Ms. Alaimo now works at the Red Mannequin, Craftworks, and in real estate.

Taking a break for a casual brunch, she recently spoke about her involvement in the formation of the Oak Bluffs Arts District, roughly the area of Dukes County Avenue near its intersection with Vineyard Avenue.

Ms. Alaimo explained that the present Arts District used to be an active business area in town. The Red Mannequin was a fruit and produce market. Periwinkle Studios was once a fish market.

“The Dragonfly was a general store that sold supplies to the people who built the Campground in 1860,” she said. “That neighborhood has a deep history as an enterprising neighborhood.”

In 1994, Ms. Alaimo and her husband bought three condemned buildings, previously used as artist’s studios and workshops. After repairs and restorations, the couple moved into their new home the next year.

She described living in the space that is now the Dragonfly Gallery. Her husband, a jazz pianist, would be playing music with their art collection hanging on the walls around him. Passersby would walk in the door and ask if the gallery was open.

“After the first year, we realized that we had a commercial space as a home. Even though we owned it, it was still resonating as a commercial space,” Ms. Alaimo said. “So I called all my friends and said, ‘I’m opening a gallery. Bring your things. Set it up. See what happens.’ And that’s how it started. Basically it happened to us. It certainly was my interest, but I didn’t expect to do exactly what I did.”

As the owner of the Dragonfly Gallery, Ms. Alaimo said she looked for something fresh in an artist. “I tried to take new artists, to work with them, and to present them,” she said. “I had great people come through there and move on to really special things. And with the fact that a lot of the artists lived with me, or in the gallery when they stayed for shows, I was able to have some really wonderful people from Boston or New York.”

Ms. Alaimo said that the installation of five businesses into the neighborhood, Periwinkle Studios, Piknik, Alison Shaw Gallery, Parr Audio, and Island Interiors, added to the existing art businesses and helped complete the core of the Oak Bluffs “Arts District,” the first of its kind on the Island. Now, there are several more businesses that have joined.

The owners of these establishments held meetings to plan advertisements or events such as art strolls, but their relationship was more about camaraderie, Ms. Alaimo said.

“The one thing that makes the art district special is that we were trying not to influence one another. These were individual studios as well as shops. Everyone needed to maintain their own personalities,” she said.

Although the district did not have formal organization or leadership while she was involved, the group may have become more structured since, she explained. Three years ago, she decided to sell Dragon Fly Gallery to Don McKillop and Susan Davy. She was happy “to move on to other adventures.”

“The first year I helped out a bit [with the Arts District], and then I realized they really didn’t need me,” she said. “I am still in touch with everyone. I still support the artists who were with me. Within the art community, we realize that it’s not that you need each other, but that it is just nice to know that there are other people who have the same struggles and the same questions. We appreciate the beauty in things. Artists question how things are done and that brings them together in a lot of ways.”

Ms. Alaimo is hoping to bring the entire community together through the second Wind Festival, to take place September 1 at Ocean Park in Oak Bluffs. The event will include a kite competition, model airplanes, a dog parade to benefit the American Cancer Society, and a group of radical kite boarders. Last year, participants built over 150 kites at the festival.

“Art should not be something that makes people feel excluded. It is an inclusive thing,” she said. “It is a beauty that everybody should embrace. And it is everywhere. Art is everywhere. It is in everybody’s window. It is in everybody’s hearts somewhere. There is something that they see.”