Even on a gray Monday after noon in mid-June, with a cool wind blowing off the sea, Oak Bluffs still feels like the place you want to be. Circuit avenue is crowded with everyone from teenagers to seniors all looking for that special memento; wherever you lie on the spectrum, you can find a place for yourself, and something you want.

This weekend Oak Bluffs opens its doors extra wide announcing itself, yet again, as the place to go for summer entertainment. Saturday, June 18 seems to pack in a full summer’s worth of events. From noon to 5 p.m. the Harborfest invites one and all to enjoy food, music, shopping, antique cars, a pet blessing, parade, and, of course, carousing. For the first time the Midsummer Faerie Festival is joining hands with Harborfest bringing Celtic musicians and a host of faerie guests to the party. In the evening and lasting until 11 p.m. the Solstice Celebration takes the baton. Circuit avenue will be closed to vehicles as pedestrians take to the street to enjoy outdoor music and dining. Fireworks are scheduled to begin at 9:15 p.m.

But Oak Bluffs is more than just a seaside resort town. It is a community that stands apart and a place where, after just a bit of time, anyone can feel at home.

Deon Thomas came to Martha’s Vineyard from Clarendon, Jamaica about 12 years ago. After opening several restaurants in different parts of the Island, he has come to rest, for now, at Deon’s on Circuit avenue. Standing behind the bar of his restaurant, Deon jokes with the patrons slinging back cocktails in the early afternoon.

As if the bar were a stage, Deon poses with his drinks before expounding on the merits of his town. “Oak Bluffs is awesome,” he exclaims. “It’s where the action is, and you wanna be where the action is.” He pauses before adding with a laugh, “But sometimes there’s too much action.”

Either way, Deon knows the real recipe for success. “We just need more sunshine.”

Dennis daRosa, president of the Oak Bluffs Association and owner of daRosa’s, marvels at the decorating facelift Deon has given the restaurant. Over coffee at Deon’s he remarks, “It’s a beautiful setup. It’s one of our nuggets of diversity in town.”

Tia Sequeira, a 12th generation Islander, who makes and serves chocolate at Ben and Bill’s, is looking forward to the weekend and summer crowds. “We get a line snaking all around the store with people waiting outside,” she says. “But you don’t mind so much, it gets you pumping, you get used to it.”

Though Ms. Sequeira lives in Edgartown she prefers Oak Bluffs to any of the other towns. “It’s friendlier here. Vineyard Haven is earthy-crunchy and Edgartown is overly priced, and it’s uncomfortable there with everyone walking around in their polo shirts.”

Oak Bluffs, she feels, is different. “Oak Bluffs is laid back. You can come in your sweatshirt and your flip-flops and no one cares.”

And it is true, while walking around town, that everyone does appear to be unconcerned with fitting in or looking the part. At Offshore Ale Co., Pedro Sene, a native of São Paolo, Brazil, sits in the corner of the restaurant rolling napkins full of silverware. His small ponytail and three facial piercings provide a contrast to his bright red Lacoste polo shirt. But it all seems to work together as he speaks about the town he has called home for four years.

“It’s easy here because it’s a young town,” he says. “It’s just chill, there’s no need to be fancy or polite. You can be rude here, you can be yourself, it’s easier to express yourself.”

There is also a sense of comfort he feels in the community he’s found here. “Oak Bluffs is my town, it’s what I like. In the other towns, you have to put up a show and fake it, but I can’t fake it.”

Nestled amidst all the action and authenticity, there is also peace and quiet to be found in Oak Bluffs in the Camp Ground, a summertime community that has become a must-see for every tourist. On this cool day the porches, usually filled with residents in rocking chairs people-watching those who watch them, are rather empty. Still, the small circle of homes feels alive with color and the rocking chairs moving about in the breeze. The homes, each one unique, transform into one long gingerbread façade, the names, colors, and quaint kitsch of it all blending together into one circle of fairytale homes.

Tomm Warburton, a concierge at the Wesley Hotel, has spent his summers at the Camp Ground since he was a boy. He likes the Wesley Hotel for retaining a sense of serenity as a part of the Camp Ground, despite the hundreds of visitors who stay there every summer. Looking out from the front desk at the hotel, he muses, “It’s a great place to work because we’ve got a window on the world. I enjoy working here so much. You almost get a barometer reading for what’s going on in town.”

Despite his generational difference from the young servers downtown, Mr. Warburton also connects to the same simplicity and freedom Oak Bluffs offers. “The diversity in town is great. There is something in Oak Bluffs that appeals to every element of the social strata. There isn’t any pretense here, and there’s a wonderful cohesion to the community.”

Even first-time visitors to the Island can tell that Oak Bluffs stands apart. Liz Malone, a visitor from central Florida, who, with her husband and another couple, is making a sailing tour of the gems of the Massachusetts coast, gushes, “Oak Bluffs is definitely a highlight of our trip because of the quaintness. And we really like the unique shops. They’re not all the same.”

Her friend, Tina Dentel, inquires after how the Island got its name. Learning that Martha may not have had a vineyard after all, she turns the name into myth. “Maybe it was just a dream, a lark,” she said.

You could say the same about Oak Bluffs, although its quiet and dreamy side may not be on view this weekend during the Harbor Festival. But Saturday promises to employ Oak Bluffs’s other special gift: It’s a great town for a party. One you wouldn’t want to miss.