It’s one thing to imagine buying a run-down, century-old general store in a ramshackle neighborhood of Oak Bluffs, fixing it up, and living the artist’s life. It’s another thing altogether to do it. To make it work, you’d need to be wildly spontaneous in the short run and fiercely committed in the long run – two opposing traits not often found in the same person, let alone the same couple.

If anyone was up to the challenge, it was Holly and John Alaimo, who met on a Friday and married the following Monday – “Hey, it was a great weekend,” says John – and who four decades later are still going strong. In 1995, they retired early (she as a Boston concierge, he a Polaroid employee), left their newly remodeled home in Lexington, and arrived at 91 Dukes County Avenue in Oak Bluffs. What they found was a place rife with history, but notably dilapidated.
    
In the first part of the century, Dukes County Avenue, lying west of the Martha’s Vineyard Camp Meeting grounds and parallel to Circuit Avenue, had been a bustling little commercial district with a bakery, fish market, general store, and firehouse. All that had faded by the late 1960s when Molly and Herbert Kahn, proprietors of Newton Pottery, bought up much of the block to create an impromptu arts colony. After Herbert, then Molly, died, the buildings fell into disrepair. An auto mechanic expressed interest in the property, but the Kahns’ son chose to revive the vision of his parents by selling three of the buildings to John and Holly Alaimo.
    
When John and Holly moved into the old general store, the upstairs quarters were unlivable. They set their futon on the ground floor, in the enclosed front porch. The heat didn’t work. It was April. The house was drafty. Snow fell. “We were freezing,” remembers Holly. “People thought we were crazy. I said, ‘Look, where else can I buy a business property that I can walk to the ocean, walk to town, and sun in my yard?’ I thought, ‘This is heaven.’ ” She was watching television in her nightgown one morning when some people wandered in to admire her artwork on the wall. Some days later, John, an accomplished pianist, was playing music when people came in for what they thought was a concert. Most folks might post a sign saying Keep Out. John and Holly decided it was a sign to set up shop; if the building was meant to be public space, so be it. They refurbished it – wood floors, raftered ceilings, white walls. In addition to Holly’s own work, they hung fine contemporary art by other Island and national artists, and opened the doors as Dragonfly Gallery.
    
The spirit and aesthetic behind this idea inspired other artists. Judy Drew, who’d been renting the former fish market from the Kahns, bought the property and opened a hand-block-printed clothing studio and boutique. Jim Parr remodeled the old bakery building and established Parr Audio, a recording studio, in the basement; his former wife Anne has Island Interiors home decorating on the first floor and a living space upstairs. Fashion stylist Michael Hunter fixed up 99 Dukes County Avenue for his home and business called Pik-Nik, which specializes in antiques and vintage housewares. Martha’s Vineyard Center for the Visual Arts bought the old firehouse and converted it to a gallery for member shows that often overlap with Dragonfly’s Saturday receptions. The area was suddenly alive with art lovers.
    
“It was sheer, wonderful luck to end up with such good neighbors,” says Judy Drew. “I feel very fortunate.” Though each of the new residents had independent goals and worked in different mediums, they were drawn together by a common interest in the arts, by the funkiness and affordability of the old industrial buildings, by the off-the-beaten-path charm and safety of the neighborhood, and by the B-1 zoning that allowed both residential and business space to share the same buildings. “We’re not in the downtown area and that’s all to our advantage,” says Michael Hunter of Pik-Nik. “I couldn’t live in my shop on, say, Commercial Street in Provincetown. I couldn’t have a garden.”
    
Oak Bluffs has long been a collection of villages, with people identifying themselves as being from a specific section, neighborhood, or district (Eastville, the Highlands, Hartford Park). Now a group had resettled another outpost of Oak Bluffs and made it a destination in its own right. Unlike the planned areas of Cottage City or the Copeland Historic District – or even Circuit Avenue, developed nearly a century and a half ago specifically to cater to crowds of vacationers – the artistic district of Dukes County Avenue came together haphazardly. Without really thinking about it, the artists established the sort of place that urban scholar Jane Jacobs had advocated years earlier in The Death and Life of Great American Cities: a historic neighborhood, saved by shops selling what residents and visitors wanted to buy.
    
Once they realized what they had, the artists of Dukes County Avenue wanted to spread the word. What they needed was a sign with their name on it. That set them to thinking about their identity as an arts district. “There are many great [arts districts],” says Ellen Weiss, professor of architecture at Tulane University and author of City in the Woods: The Life and Design of an American Camp Meeting on Martha’s Vineyard. “The Design Districts in Miami and San Francisco, and here in New Orleans, the Warehouse District. All of these, along with the Oak Bluffs version, depend on an intelligent reuse of historic buildings in intimately scaled neighborhoods that have a variety of building types and usages, so that people will walk from building to building and enjoy the ambience.” The Vineyarders were certainly thinking in this vein, but should they call themselves Little SoHo or The SoHo of Oak Bluffs? Or should they pick a name that suggested something more homespun? In the end, they decided their identity drew less from the ultra-cool urban art scene and more from the character of the working-class folks whose buildings they now 
inhabited. Fine arts in a fine location. They would call themselves Arts District, plain and simple.
    
They were just being themselves, and that meant you could be, too. Author John Villani, who included the Vineyard in his book The 100 Best Small Art Towns in America, was all in favor of the result: “In a small art-town gallery, people don’t have to contend with the absurdly comic snobbery of buzz-cut, bleached, pierced, and black-jacketed gallery owners hiding behind paper-thin shields of elitist affectation.” Where other arts districts might have fern bars or beret-filled coffee bistros, this side street in Oak Bluffs had Tony’s Market – you could have coffee and doughnuts in the morning on one side of the street, wine and cheese at an evening reception on the other. For years Holly had given directions to Dragonfly Gallery in relation to Tony’s Market. Recently she was delighted to hear Tony’s bill itself on the radio as located in the Arts District, “where every sandwich is a piece of art.” When she heard that, she thought, “Boy, this is really something. We’ve got it made now.”
    
To an outsider, Circuit Avenue – the town’s Main Street – might seem the better place to draw customers, but to the residents of the parallel universe of Dukes County Avenue, it isn’t. “We add something to Oak Bluffs,” says Chris Dreyer, co-president of the Martha’s Vineyard Center for the Visual Arts, “which is a place you can get to without going through the mishmash of Circuit Avenue. To get here, you can go the back way and end up in a safe neighborhood with places to park and affordable art in a range of styles made by a great many outstanding artists.”
    
“It’s a bit of a destination,” says Michael Hunter of Pik-Nik. “It’s not like we have to babysit the ice-cream lickers all day long. We may be busy for a while, then quiet for a few hours, and I’ll have time to paint a set of chairs or garden.”
    
The ebb and flow of visitors means that Judy Drew can design her next block print while her shop is open, or that interior designer Anne Parr can stop in to consult with Judy on some fabric for her next project. It means that the CD of John Alaimo’s jazz piano music that’s playing at Dragonfly Gallery can be recorded across the street at the first-class recording studios of Parr Audio. It means that sculptor Tom Carberry, who organizes weekly life-drawing classes upstairs in the Firehouse Gallery, can go across the street to Dragonfly to show Holly his bronze cherub sculpture. “We all work alone,” says Judy Drew, “but we’re so close that if you need an opinion or a walk to Tony’s, you can always grab someone for company and support. It’s the best of both worlds.”
    
With such a magical balance, the danger is that it might tip. Other arts districts have outgrown their roots. “Arts communities tend to gentrify their neighborhoods and eventually price themselves out,” notes Ellen Weiss. The key to preventing the Arts District from going the way of SoHo and Tribeca – which are now too upscale for most of the artists who were first drawn to them and made them valuable – is zoning that protects the character of the historic neighborhood. Weiss sees that happening in Oak Bluffs. “Its preservation proves that there has been smart planning, protecting community values,” says Weiss.
    
After a decade, it’s not so much that the Arts District may break apart because of the pressures of the marketplace, but that it still remains a few “cards short of a deck,” as Michael Hunter puts it. The artists want to encourage more people like them to come in. “The key to surviving here is to own your gallery space,” says Holly.
    
When the Alaimos first moved into their run-down buildings, Holly showed her own artwork almost exclusively. But within the first year, she realized it was important to promote the neighborhood and other artists as well. In the process, everything and everyone has come together around her. “It’s like this strange little planetary center,” she says. “There’s an energy source in this building that allows people to connect.” She realizes now that the canvas of her creativity is larger than she originally thought. Although she still makes the occasional concrete relief or mosaic, her real creative outlet lies more in making the gallery and neighborhood shine.
    
Though she and John will continue to live in Oak Bluffs, run Dragonfly Gallery, and perform live music, they no longer want to juggle the upkeep of three buildings. “We are looking for someone else who has the same dream to give it a positive push,” says Holly at presstime. To entice other artists, the Alaimos are offering their three-bedroom Camp Ground 
cottage next door to the gallery at a reasonable price. “I feel like I’m guarding this precious little thing,” says Holly of the neighborhood and its potential.
    
“A lot of people dream of this,” says Pik-Nik proprietor Michael Hunter, “but you can’t just think of it. It’s something that you have to make happen.” For those who aren’t yet ready to make the move, there is still the option to visit. Chances are you’ll find a piece of an artist’s life to take home with you to call your own.