This Saturday marks the fifth annual Art Stroll in the ever-expanding arts district in Oak Bluffs. The evening promises to be as eclectic as the tenants of the district, with traditional seascapes displayed adjacent to steampunk mechanical dinosaurs. The diversity of work represents the growing vocabulary of art on the Vineyard, which has found its fullest expression in this bohemian corner tucked away on Dukes County avenue.

For Dragonfly Fine Arts Gallery owner and painter Don McKillop the evening is all about increasing Island awareness of the burgeoning community of artists and galleries that has sprouted up there over the years.

“A number of people when they come in, we ask, ‘Is this your first time?’ and they say ‘Yeah,’ and then when we ask if they’re new to the Vineyard they say, ‘No, we’ve lived here for 30 years and never knew this was here.’”

Mr. McKillop, who bought the studio two years ago with his wife, Susan Davy — who is herself a photographer — has about 25 artists on display in a constantly rotating collection, spanning all styles and mediums, from Morgan Madison’s Mondrian-like, multi-layered fused glassworks to Island favorite Adam Thompson’s spare and striking depictions of local vehicles. Also on offer are Peter Batchelder, whose evocative twilight-soaked barns are instantly recognizable, and local truck driver Traeger diPietro, whose maritime tableaus evoke an abstracted Winslow Homer, among many more.

From 4 to 7 p.m. on Saturday the gallery opens its doors and invites Island jazz keyboardist John Alaimo to accompany the increasingly popular stroll, a night of art, food and socializing.

Just up the road from Mr. McKillop is Michael Hunter’s PikNik Art and Apparel.

“I don’t know where Michael finds his stuff,” says Mr. McKillop, “It’s always funky. He draws the crowds.”

For Saturday’s event Mr. Hunter has prepared a show of nine artists, all of whom will be showing their art for the first time on the Island. Mr. Hunter has dubbed the show “Primo Tempere Pictoris in Insula” (Latin for “First Time Artists on the Island”) to reflect this fact.

“The whole ‘new artists thing’ is a little patronizing in my mind, because they’re really not new artists, even though they might be new to here, so that was my point with the title.”

Among Mr. Hunter’s diverse collection are the photorealistic canvases of Frances McGuire’s Oak Bluffs sea wall; a scene at once extremely familiar to locals but rendered with a singular attention, producing an abandoned and disorienting effect.

“It’s a really gorgeous contemporary take on something that’s so mundane but that she just makes come to life,” says Mr. Hunter. “It’s so iconic, everybody knows that shot. “

Equally striking are the totem poles and dinosaurs composed entirely of spare mechanical parts and scrap metal of Walter Monstream, which tower next to PikNik; or the psychedelic surfing-inspired works of Michael Miller, five of which have been purchased by the MTA of Manhattan to be converted into 15 foot murals on the A line to JFK. Mr. Hunter emphasized the difficulty in bringing together such an eclectic show.

“A big part of a show like this is the planning which takes the better part of a year,” he said. “People might not realize that. You’re dealing with nine different souls and their personal private work, so there’s building that relationship and that trust, and then there’s the physically getting all the work here.” (As of Wednesday two of Mr. Hunter’s paintings were held up in customs from France).

“The work that Michael does and the work I do — we’re trying to stretch the definition of what is considered art on the Vineyard,” said Angel Quinonez of Amity Ink, which sits just across from Dragonfly, shares a building with Stephanie Wolf Jewelry Design and is adjacent to the Alison Shaw Gallery, in the heart of the district.

Mr. Quinonez is primarily a tattoo artist, but the walls of his shop are lined with an impressive collection of paintings, photographs, metalworks and, perhaps most interestingly, needlepoint, which he plans to display on Saturday.

The needlepoint is that of Ray Materson, a Michigan native who spent 15 years in prison for drug-related crimes. While in prison he recalled the enjoyment he derived practicing needlepoint with his grandmother when he was a child and began bartering cigarettes for tube socks which he would unravel and use as thread. Using a needle he bribed from a guard Mr. Materson began to sew, both the idyllic scenes of his childhood along with horrific representations of drug abuse and prison life. The tiny works, which need to be seen to be believed, are marvels of miniature. Highlights include a reproduction of an Ozzie Smith baseball card and a sepia-toned photograph from a grandfather’s photo album.

“He documented his whole life story in needlepoint! From jail!” said Mr. Quinonez, who is friends with Mr. Materson.

“This is thread from socks, okay?” he says, indicating the lettering on Ozzie Smith’s jersey. ““Look at the detail right there. Are you nuts?”

Mr. Quinonez is a painter himself, not only of skin but also of the more traditional easel and canvas variety. His series of purple and blue quahaug paintings seem destined to become an iconic Island print.

“The old ladies walk in to see the art, then they see the tattoo needle and go ‘Ah!’ I have to go, ‘Don’t worry, I’m not going to tattoo you for free.’”

“It’s like a version of wampum for your house,” said Stephanie Wolf of Stephanie Wolf Jewelry Design. “If you can’t wear jewelry in your living room, you can put Angel’s clam paintings on your wall. Aren’t they gorgeous?”

Ms. Wolf will be displaying her jewelry at the art stroll on Saturday as well. Inspired by the ocean, Ms. Wolf’s work uses recycled glass as well as tile mosaics. Even though her jewelry has been worn by Gwen Ifill on a broadcast of the Newshour on PBS, the art stroll has been one of the best ways for her to get her work seen by the public.

With Alison Shaw opening her new show, Dock, next door, a typically arresting collection of photographs of that old Island mainstay, and Tom Dunlop signing copies with her of their new book, Schooner, for the stroll on Saturday, Dukes County avenue will be the epicenter of the Martha’s Vineyard art world, if it isn’t already permanently.

“Everyone’s got something different to offer and it becomes a real party,” said Mr. McKillop. “It’s really a social event. There’s so many people it’s hard to see the art sometimes.”