Sitting in her childhood home, Charlotte Rose Benjamin can’t help but get a faraway glint in her eye while talking about Cumberland Farms in Vineyard Haven. Her latest album, Dreamtina, features an ode to “Cumbie’s Parking Lot” and the love won and lost there.

“Every great night began or ended in the Cumbie’s Parking Lot,” Ms. Benjamin said. “People smoked weed there, met up after parties, held sexual rendezvous, or just stopped by to get a late-night snack. The song itself is about a crush I had that didn’t like me back, which happened a lot in high school.”

After moving to New York to pursue a music career at 18, Ms. Benjamin has returned to the Island intermittently, most recently for her show tonight, August 3, at The Loft in Oak Bluffs, before she embarks on a three-week tour in September. The show begins at 8 p.m.

Charlotte and Zoe have been friends since birth. Tonight they play the Loft; show begins at 8 p.m. — Jeanna Shepard

On stage with her will be best friend and bass player, fellow Islander Zoe Zeeman, who will also join her on tour.

The women have been friends since birth.

“When my mom found out she was pregnant with a girl, her first thought was, ‘Oh, now Zoe can have a friend,” Ms. Benjamin said when asked how she and Zoe met.

As if on cue, Ms. Benjamin’s mom, Sandra Stone Benjamin, calls out from another room.

“You need to see the bathtub picture — I’ll go get it.”

She returns with a framed photograph of Ms. Zeeman and Ms. Benjamin as toddlers sitting in the bath together. The two girls, now in their late twenties, seem to take it in stride.

Ms. Zeeman and Ms. Benjamin are the daughters of two other prominent local musicians, Jon Zeeman and Mike Benjamin. Mr. Zeeman and Mr. Benjamin have been playing together for 35 or 40 years depending on who you ask, first on the Island, then in New York, and then back again. They have played in countless wedding bands and a number of individual projects, but are perhaps best known as a duo for their Grateful Dead cover band, the Grateful Dread.

Sitting at the dining room table together with the daughters, the two music veterans share an ease with each other that comes from decades of experience.

The daughters credit their fathers with their love of music and help learning the craft. — Jeanna Shepard

“It just gets easier and easier the longer you play with someone,” Mr. Benjamin said. “You know exactly what the other person is going to do, where they’re going when they play a riff.”

That experience has passed on to the next generation. Both Ms. Zeeman and Ms. Benjamin took to music more or less immediately, accompanying their fathers to gigs and later forming their own projects.

“I first played violin, which I hated and dropped for guitar, which I thought was much cooler,” Ms. Zeeman recalled. “I learned bass when I was 16, and that felt much more natural than anything I had played before.”

Ms. Zeeman now plays bass in a number of bands around New York, most recently touring with the Los Angeles-based group TV Girl in Ireland and the U.K. She wrote the bass parts for Dreamtina and toured with the Charlotte Rose Benjamin Band during their show at South by Southwest the past year.

“She took to bass immediately,” Mr. Zeeman said. “We had her learn a couple songs and hop in a set one day, and from then on everyone kept asking, ‘Well, why don’t we bring Zoe along?’”

Ms. Zeeman doesn’t remember every gig fondly.

“It wasn’t actually that fun to be 16 in a bar where you can’t drink waiting for your dad to finish his beer,” Ms. Zeeman said. “My dad would be talking to someone, chilling out after a show, and I’d just be like, ‘Dad, when can we go home?’”

Zoe began by playing bass in her father's band. — Jeanna Shepard

Ms. Benjamin started playing gigs even earlier than Ms. Zeeman, if you count any public space as a gig.

“As soon as I could sing, I would sing to anyone who would listen,” Ms. Benjamin said. “My dad would prop me up in a restaurant and get everyone’s attention and I would just go at it. I loved to perform. I loved hearing people clap at the end.”

Both girls credit their fathers for teaching them nearly everything they know about music, even as they have struck out on their own.

“With Charlotte pursuing her own artistry, there’s not much I can get involved in,” Mr. Benjamin said. “She’s doing that all on her own. When they were recording, I let her use my studio space, but even then, she was very capable and with a very talented producer, so I let them do their own thing.”

Dreamtina takes inspiration from female rock icons like Liz Phair and Fiona Apple. Songs like Slot Machine and Satisfied mourn and lambast ex-lovers over punky instrumentals. It’s a decidedly contemporary sound, and a far cry from the acoustic covers she and Ms. Zeeman first performed together as adolescents.

“Our first ‘gig’ together was actually at the Chilmark Community Center,” Ms. Zeeman said. “We were 13, playing at [a friend’s] birthday party.”

Mike Benjamin and Jon Zeeman play in the Grateful Dread together, along with numerous other bands. — Jeanna Shepard

After months of recording and a pandemic delay that pushed her South by Southwest performance back a year, Ms. Benjamin is excited to get back on the road. In September, she joins Langhorne Slim on their U.S. tour, performing Dreamtina live to new audiences.

“It’s nice to be touring with an established band so I don’t have to text everyone I know to come out so the show doesn’t look pathetic,” she laughed, adding, “I can’t wait to be on tour. I just want to be on tour forever. It feels like an adventure.”

Despite years of live performance experience, Ms. Benjamin still has one lesson she wants to learn from her father.

“My dad can just command a room in a way that I never could,” Ms. Benjamin said. “He can get everyone’s attention, he can make everyone start clapping and burst into song just from nothing. I still want to learn to do that.”