Liz DiSessa has lived on the Island for close to 30 years. A longtime musician she created Heart Roots Music nearly a decade ago which books national acts around the country. Nearly all of her work has been for off-Island events, frequently in rural areas where it’s hard to get acts to tour, and yet the demand is high in these isolated communities, particularly among young people.

Recently, she was talking to Ryan Schwab-Doyon, the new director of Alex’s Place, the teen center at the YMCA, about her work and she was struck by how closely the Vineyard fits that description too. Very quickly the two decided to bring a show to Alex’s Place, with plans for a few more in the off-season.

The first show is this Sunday, Oct. 22, and features Victor and Penny, a duo that bills themselves as a Musical Time Capsule, and brings to life both the music and origins of Kansas City swing. They also crush on the ukulele.

“I wanted to start with something that would appeal across generations,” Ms. DiSessa said. “Older people like the swing, and young people love the fiery ukulele.”

The concert begins at 6:30 p.m., and there will be a ukulele workshop from 1:30 to 3 p.m. given by Victor and Penny, whose real names are Jeff Freling and Erin McGrane. In addition to touring together, Mr. Freling was the musical director for the Blue Man Group and Ms. McGrane is an actress, staring in Up in the Air and other movies.

“And there will be a meet and greet after the show,” Ms. DiSessa said.

The duo will also perform at the Port Hunter on Saturday, Oct. 21.

Ms. DiSessa is excited about the prospect of creating a vibrant series for the off-season. “This first one is to put a stake in the ground,” she said. “And then do four events this year. And to do things that are different, not what you know.”