It starts quietly. A few flannel-clad regulars sitting at the bar, sipping on whatever suits their fancy, which, despite it being called the Ritz, is never fancy. The walls, like a college activity board, are layered in pictures of performers past, the beer fridge plastered in overlapping bumper stickers. The dancing hasn’t yet begun, just some bobbing, some head nodding, and some half-stares at the woman in the corner you think you know, or at the man in the back who you hope you don’t.

Then it starts to pick up. A blonde lipsticked lady — her name is Rose Guerin and she performed on Ringo Starr’s last album — plays the guitar, centrifuging what seems like the energy of the universe into every song she sings and every string she strums. The rest of the bar feels it. Work boots start to stick to the wooden floor, covered in a decades-old cocktail of disinfectant and $3 PBR. The room fills with sequined dresses and Carhartt hats. Everything starts to sparkle under the ceiling’s spiral of Christmas lights. The disco ball finally has something it wants to reflect.

It’s 9 p.m. on a Saturday in early February and the only thing awake on Circuit avenue are the Oak Bluffs skunks, skittering down the road like the Vineyard’s version of a wintertime tumbleweed. But inside the Ritz, the Island’s winter music scene has come alive.

“That’s generally how we start the night,” Ms. Guerin said. “It’s like a listening room in there . . . And then things get rowdy at the break. And then it starts to get crazy.”

When most everyone else on the Island leaves, the bands and performers everyone knows from the summer largely remain — not just in photos on the wall but often bouncing off them. In one frigid January week alone, Johnny Hoy and the Bluefish, the Edbury All-Stars, the Dock Dance Band, the Brother’s McMahon and of course, the inimitable Ms. Guerin graced the Ritz’s stage (or lack thereof). The music ranged from blues to funk to soul to pop to rock to honky tonk to “Vineyard stuff.” And they bring their own eccentric hordes of Vineyard year-rounders with them, emerging from the woodwork to enjoy the music they love on an Island they can finally call their own.

Year-round music scene is always hopping. — Jeanna Shepard

“This is when people get their Island back, and the community sees it as a time to come together,” said Ritz general manager and set scheduler Kelly Feirtag. “If you want to go out and have a good time, you will. Because it’s the Ritz. We know everyone by name. We know everything they will drink. We know where they’ll sit. And anything can happen.”

“Anything” ranges from dancing on the bar to the fire alarm going off at 12:30 a.m. because of a “paint fume situation.” When that happened two weeks ago, Ms. Guerin played on, the tone a welcome metronome for what had to become an improvised trance song. Nobody cared one bit.

“It’s the time where people probably try to get a little more experimental, take bigger chances, because you can,” Ms. Guerin said. “Falling on your face isn’t that hard when you’ve got people who are going to catch you.”

The Ritz isn’t the only spot to see a show in February. But unlike the summer, there is no pastel-colored, teenage menagerie dock-dancing under Memorial Wharf or senior acts at the Old Whaling Church. Instead, a seasonal summer restaurant (the Chilmark Tavern) is converted into an ad-hoc acoustic music venue (Pathways) and the Chilmark Community Center becomes the home of the potluck jam, hosting everything from ex-hippies who play an Indian box-accordion called the Shruti to fishermen keen on a different kind of bass. Bands with names like Jellybone Rivers and The Maniacs of the Heart kick it at the Portuguese American Club one night and the winter’s farmers’ market the next morning. The Dock Dance Band occasionally decides to come up from the Caribbean for a show. And the Ritz serves as the center of it all — making live music one of the few Vineyard activities that are truly year-round and accessible.

“The owners like to think of the Ritz as a community fire that people gather around,” Ms. Guerin said, referring to Larkin and Jacqueline Stallings. “A comfortable place to go and be warm, because it gets cold out there. But we are open year-round. And we will have music for you.”

Delanie Pickering, relatively new to the Bluefish lineup. — Jeanna Shepard

Of course, it all sort of started with bluesman Johnny Hoy. The now-infamous stonemason, fisherman and harmonica maestro, flush off three decades of wedding gigs, still plays at the bar with his Bluefish every Wednesday.

“You try not to compare yourself to Johnny Hoy,” Ms. Guerin said. “But the thing that makes him so special is that he’s very encouraging for people to get up and try. He’ll pull people out of the crowd and get them started. And he definitely has a communal, creative spirit. He brought that to the Ritz.”

Along with the iconic pianist Jeremy Berlin, Mr. Hoy tapped not long ago two new Bluefish for the band — drummer Kevin Medeiros and guitarist Delanie Pickering, who was literally plucked from the crowd.

And they aren’t the only newcomers on the music scene. Ms. Guerin, who’s been at it for nearly a decade, rattled off a list of musicians even she didn’t know about until recently, including Maryse Smith, who she invited on stage with the Dock Dance Band last Friday night.

“I wasn’t honestly that aware of the Vineyard music scene at all before I moved home,” Ms. Guerin said. “I’m not surprised, now that I know what kind of a hot bed of creativity this Island gives to you. But still, the creativity, the talent here, is pretty astounding. And you know what? You never run out.”

Kelly Feirtag and Rose Guerin earlier this year organizing Ladyfest. — Mark Alan Lovewell

Other newcomers have established themselves on the circuit. The Brothers McMahon, a heavily-bearded trio from western Massachusetts that has been gigging on the Island since 2017, now play every Sunday at the Ritz and every Friday at Town MV, mixing in shows at The Loft, Offshore Ale and elsewhere. When there’s an opening on Saturday, they’ll play then too. Setlists might start with Bruce Springsteen and Johnny Cash, an inferno of I’m On Fire and Ring of Fire arriving in a one-two punch. They then Take a Load Off Annie

and play an 11-minute version of This Is the Place by The Talking Heads.

“We like to take things really psychedelically,” guitarist and singer Sean McMahon said. “We like to stretch it out.”

Sean looks like the iconic images of Jesus, and he plays guitar like a believer too — especially on Sundays, when he leads the Community Baptist Church of Gay Head (Aquinnah) in song. His brother Griffin looks a little less like Jesus, but the way his fingers float on the keyboard might well represent the second coming. And their cousin Ted McGuinness looks kind of like a muscular Jesus. He plays the drums. Religiously.

“I’m so lucky to have them,” Mr. McGuinness said of his cousins. “They’re like fire and ice. And I’m like water.”

Where everyone knows your name and your song. — Jeanna Shepard

The brothers live on the Vineyard year-round now. Sean is married to singer Siren Mayhew. Griffin is engaged. And their following extends far beyond the family.

“Well all met Griffin first, which was fabulous, and we were all mind blown,” Ms. Guerin said. “Then Sean showed up, and then Ted, and the three of them together, they’re amazing. They do literally everything from Michael Jackson to an entire set of old truck driving songs. They’re the most versatile. And they’re so much fun to play with.”

But the unquestioned center of the winter music scene is Ms. Guerin herself. She grew up in a musical family in Chilmark and spent years touring the world with her band Vandaveer (that’s how she met Ringo). She came back in 2013 and has been on the Island ever since. She and Ms. Feirtag organize an all-female show in October called Lady Fest. When musicians are asked about the winter bar music scene, she’s the first person they mention. It’s not really a Ritz show without her.

“It feels like a million different things when you’re playing up there,” Ms. Guerin said. “But what I think I try to strive for is to be some conduit of spirit. To let something flow

through you and pour out, because you are trying to make a connection. That’s what it is.”

Ms. Guerin’s physicality on stage forces her to make a connection with everyone she plays and all who watch. That’s what music is for her — a form of intimacy. And that’s what makes it so special on the Island, especially in the off-season.

This Friday, Valentine’s Day, is The Ritz Prom, with Ted and Sean playing. Ms. Guerin is on the night after. It’s guaranteed to be an intimate affair.

“I just love music,” Ms. Guerin said. “It’s my purpose, and I don’t what else to do.”