Outerland, the Island’s only nightclub, is up for sale. Aboveground Records and Offshore Ale have cut back on their performances. The Oyster Bar’s entertainment license was revoked this summer. The Wintertide is gone. The old Atlantic Connection is now an amusement arcade.

Is it that hard to put on a little music?

Well, clearly Vineyard music promotion is a tough racket, but the pervading sentiment of those working in music on the Island is that it can be done.

The co-owner of Aboveground Records in Edgartown, Chris Liberato, is a longtime promoter who has consistently lured interesting independent acts to the Island and found impressive audiences for the shows. He thinks that a viable club is both possible and necessary.

“It’s my firm belief that clubs could survive and be financially successful here,” he said.

“Having had my feet a little bit in the water, I’ve seen that every club in the world makes money off the bar, not ticket prices. Outerland tried to cover all the price in the ticket costs,” he added.

“Another issue with music is you need to mix it up. You can’t bore your audience,” he said, “But look at the papers in Boston, they have great acts every night of the week. Why aren’t they playing here on a slightly off night?”

There are some clear logistical obstacles to booking off-Island music. First, Martha’s Vineyard does not fall naturally on a tour schedule.

Then, those musicians who get near enough could potentially at least be contractually obliged to stay away.

The director of marketing at the Cape Cod Melody Tent, Paula Gates, said all their booking contracts prevent musicians performing at another venue within a certain amount of miles for a period of time around the show.

“It’s standard industry practice,” she said. “You’d be stupid to say that’s okay.”

But it is unclear in practice how much of a factor such a limitation would be for the Island. Several promoters consulted for this article said they had never run into the issue. Ms. Gates said there shouldn’t be much crossover with artists from the Melody Tent, which have recently included LeAnn Rimes and Tony Bennett.

“Most of our performers, you don’t see them playing small clubs — to many of them, our place is very small at 2,220 seats,” she said.

Then the costs and time associated with a trip to the Island are substantial. Providence or Boston is a day trip, and the Vineyard is not a cheap place for accommodation.

There are ways around the problem: Whitney Daley worked as talent advance manager at Outerland, booking hip-hop DJ RJD2 for the club earlier this summer. Though he was not on tour, she was able to entice him to fly from Philadelphia and stay for the weekend.

“It’s a built-in vacation, that was our negotiating power. But it’s a help and a hindrance, the Island aspect.”

Putting on a successful show on the Vineyard takes special effort, conceded Mr. Liberato.

“It takes a lot of people banding together,” he said. He helped facilitate a recent show with Brooklyn band Death Vessel at Che’s Lounge.

But it wasn’t easy: Death Vessel left the tour van at Woods Hole and came over on foot with minimal equipment, to save on ferry costs. Mr. Liberato was one of a team of around eight providing, among other things, an on-Island stand-up bass to help pull off the show.

“He had come before, he knew he’d have a good time and trusted he wasn’t going to be treated poorly,” he said. “And Che’s is the best gig in town.”

As for population, Mr. Liberato said that issue, too, should be possible to overcome.

“I’ve seen off-season as more successful than summer. People are starved for things to do,” he said.

In 2006, Mr. Liberato helped bring over post-rock band Cul-De-Sac which played a a live sound track to the film Faust at the Katharine Cornell Theatre.

“It was a cold day in November and it was packed,” he said. “The Vineyard is unique in that people come when you do something different. They’re not stuck-up about something new. Boston audiences are uptight. Here people just try it.”

He pointed to KCT Concert series run by Mary Wolverton and Gregg Harcourt, a nonprofit which regularly brings folk, Celtic and bluegrass music to the Vineyard. Next Saturday KCT is bringing North Carolinian bluegrass singer Shannon Whitworth to play at the Katharine Cornell Theatre. They have brought the acclaimed folk group Old Crow Medicine Show here twice. Grammy-winning singer Gillian Welch joined them at one of the shows.

“They love the music they love,” Mr. Liberato said, “and they do it just on small grants.”

Last fall three musicians, Alex Karalekas, Brad Tucker of Ballyhoo and Willy Mason, banded together to put on two musical potlucks over Thanksgiving weekend at the West Tisbury Grange Hall and the Chilmark Community Center.

Both shows went for over four hours, boasted more than a dozen sets and, as a showcase of musical talent, rivalled many major circuit music festivals. The success of the evening led to regular events through the winter managed by Mr. Karalekas, who was given the ability by enthusiastic selectmen to book the Chilmark Community Center on short notice. After a summer break, he has booked the center for Oct. 11 and for a Thanksgiving show Nov. 29.

Mr. Karalekas plans the shows around the phases of the moon, to help ensure good vibes. “The waxing moon let me down once though — people weren’t that social,” he said, “The Thanksgiving night will be the big one. I want to be careful not to do too many — I want to keep it new.”

Mr. Mason predicted the Island music community will feel the loss of the Outerland.

“I think it is a big deal,” he said. “A number of venues keep the local scene going to at least an equal extent, if not more, than when I was growing up. But having off-Island musicians is important for musicians to feed off and get fresh ideas. I do wish there was a good club here. It’s a big hole. Hopefully it can be filled. The population is so shifty it’s hard to maintain a venue, but I think [a club] could work if done right.”

He added that live shows are an important part of social life on the Island, particularly in the winter.

“We’re not living in the suburbs where you walk down the streets and see people,” he said. “It’s parties and shows where you’re used to seeing people in the same numbers as at schools. Without the venues, and with the parties getting shut down, I don’t know what people will do.”

Che’s Lounge on Main street, Vineyard Haven is a rare venue success story here. The alleyway coffee shop which has a capacity of less than 50 opened in 2006.

Early this year co-owner P.J. Woodford teamed up with Colin Ruel, an Island musician who had played at the cafe in an evening of music he had helped to arrange, to put on regular nights of entertainment.

Mr. Ruel assumed the role of promoter and quickly established a following for the venue with themed multi-act bills.

The coffee shop has blended regulars such as Nina Violet, Sofi Thanhauser, Chorus of Arrows, Yes Future Yes, and Willy Mason, with critically acclaimed national and international musicians including Mara Carlyle, Bradford Reed and recently Death Vessel.

“Even if it’s by default I’ll take it,” said Mr. Woodford, of Che’s new status as the off-Island musicians’ venue.

Mr. Woodford says the place is breaking even off the back of the music, but the cover charges range from $5 to $15, and without a liquor license it’s a low-margin operation.

“Hopefully it’ll be self-perpetuating. It’s a business, no matter how boho you are,” he said. “Musicians deserve to be paid.”

But he said the venue’s built-in limitations — being in Vineyard Haven it is bring-your-own — are also part of its charm.

“For me the vibe is great. Musicians really like the set-up, and when people turn up they’re really committed to listen. It’ll never be Wembley stadium but I love that about it,” he said.