Victor and Penny bring vintage-flair tunes to the Island

Victor and Penny will perform at the Port Hunter in Edgartown, and at Alex’s Place at the YMCA this weekend. Courtesy YMCA.

Direct from Kansas City, Mo., a unique musical experience is coming to the Vineyard for two performances this coming weekend. Veteran musicians Victor and Penny put their own very cool spin on original songs reminiscent of Prohibition-era jazz. The married couple (real names Jeff Freling and Erin McGrane) tour all over the country, both as a duo and with their band, the Loose Change Orchestra, and they will be heading to the Island in between appearances at New York City clubs.

On Saturday, Oct. 21, Victor and Penny will perform at the Port Hunter in Edgartown. On Sunday, Alex’s Place at the YMCA will host an evening with the duo billed as “A highly entertaining, living musical history lesson.” A workshop with Ms. McGrane and Mr. Freling, titled “Ukulele/Guitar as a Rhythm Instrument,” will precede the Sunday performance at the Y.

The Sunday all-ages show will include a performance of original songs peppered with tidbits that illuminate the roots and evolution of Kansas City jazz.

“It isn’t a tribute or a lecture,” says Liz DiSessa of West Tisbury, who serves as booking agent for the duo through her business, Heart Root Music. “I call it a presentation, but it’s really a concert. There’s nothing heavy-handed. You get to experience talented musicians performing fun music, but you also get this really beautiful dialogue about where the roots came from. People walk out from their shows with smiles on their faces.”

Ms. DiSessa compares Victor and Penny’s style to other genre-blending groups like Boston’s Lake Street Dive.

The couple’s music ranges from smoky ballads to bouncy hook-laden tunes, all with a vintage flair — a style they call “swing-infused folk-jazz.” Whether you’re a fan of jazz or just interested in musical history, the catchy tunes and musical artistry of these two seasoned professionals are more than enough to encourage attendance.

Mr. Freling is a master guitarist whose dazzling solos alone are worth the ticket price. Ms. McGrane, who sings and plays ukulele, has a polished voice through which her sparkling personality shines through. She can do peppy ’30s pop singer or wistful chanteuse with equal ease. Mr. Freling also sings, and together the two harmonize beautifully.

It’s not surprising that the two artists present a tight and polished performance. Victor and Penny have performed more than 1,000 times in the past five years at venues both large and small. And they are both veteran musicians with music and theater backgrounds as varied as they are impressive.

Mr. Freling is a Berklee-trained composer, arranger, and instrumentalist who has contributed compositions to a number of films, TV shows, and theater projects. He performed with the Blue Man Group in Chicago and has lent his considerable talent to a variety of musical and creative projects.

As well as a musician and composer, the lovely, willowy Ms. McGrane is also an actress who appeared in the film “Up in the Air” with George Clooney.

Ms. DiSessa, who handles many national acts, first caught a performance by Victor and Penny in Boston, and was captivated enough to sign them on. This will be her first experiment with bringing outside artists to the Vineyard, and she hopes to continue booking both musicians and other acts throughout the off-season.

“I work with a lot of different artists,” she says. “The reason we chose these folks is that they have an amazing crossover appeal. A lot of younger people like them as well as an older audience. They play hot, fiery jazz and do it really well. They have a lot of energy.”

Ms. DiSessa encourages those unfamiliar with the performance space at Alex’s Place to check it out. She notes that the nightclub-style listening room has great acoustics and boasts state-of-the-art sound equipment. Alex’s Place has a history of hosting musicians and performers from all over the country, many of whom opt to play there instead of one of the Island’s many bars. The space is alcohol-free and designed to feel like a cabaret. A portion of the proceeds from the show will benefit the teen center.

Victor and Penny perform a 21-plus show at the Port Hunter in Edgartown, Saturday, Oct 21. They present a “Musical Time Capsule: the Renaissance of Antique Pop” on Sunday, Oct. 22, at Alex’s Place. Doors open 6 pm, showtime is 6:30-8 pm, with a meet-and-greet after. (Tickets $15 advance, $20 at the door.) The Ukulele/Guitar Workshop with Victor and Penny: Sunday, Oct. 22, at Alex’s Place at 1:30 pm ($20 or $15 if purchased along with tickets to the evening show).