Meet the Weilands

Oak Bluffs School music teacher Brian Weiland and his traveling family band.


The Weilands live down a dirt road in Oak Bluffs, one you’ll miss if you aren’t paying attention, so they literally live off the beaten path. Mom and Dad, Jennifer and Brian, have been on the Island since the mid-1990s, after Brian slipped into a full-time job teaching music at the Oak Bluffs School.

“I used to come here and drive tour buses in the summertime during college,” Brian remembers, “then we weren’t sure if we would be able to afford to stay here, so we kept working in the summertime, and I graduated with my degree in music education, and right after that, the music teacher in O.B. went on maternity leave, and I was her replacement. She decided to leave permanently, and I slid in and got hired in 1998. It’s my 24th year, I’m almost at my 25-year anniversary.” 

Jenn spent 20 years as a family childcare provider at home before moving on to teach special education at the Charter School. They raised their family here — three children: Liam, 22, Avalon, 20, and Aiden, 15 — plus two cats just beyond kittenhood, and a dog named Quinn. The Weiland house is filled with musical instruments, a hammered dulcimer in the living room, guitars hanging on the wall, Avalon’s harp nearby. Brian says he met Jenn in college when she saw him perform and decided she wanted to take guitar lessons. 

“I think she managed to learn one song and then we got distracted,” he laughed. “She also plays the violin and she sings, but she doesn’t really like to do it in public. My family was onstage one time at a show and someone said to her, ‘You should be up there too,’ and she said, ‘Somebody has to drive the bus.’”

Brian said his dream was to play all instruments, but mostly he plays the hammered dulcimer and guitar. He majored in percussion in college, he says, and plays on the Island with the Flying Elbows, and was a drummer in the Day Trippers back in the day. You can find Brian in the orchestra pit during the high school musicals, or onstage at the M.V. Playhouse’s many musical events. He’s sat in with all kinds of musicians, sort of an auxiliary player, filling in anyplace he’s needed. 

You would think with a family full of musicians at home, Brian would have grown up himself in a house filled with music, but that’s not the case. His parents didn’t think music was a good career path, Brian says. 

“I always knew I wanted to be a musician,” Brian says. “My earliest memories are of music. I remember seeing a guitar and thinking, ‘When I’m big enough, I’m gonna make that thing work.’ I didn’t really have a wildly supportive musical family.” 

Brian played in the school band, and was a musician throughout high school, but ended up joining the Army, where he was an air traffic controller, something he did mostly to pay for college, he explained. “I still didn’t study music right away, because I was always told that wasn’t really a thing to do. All my friends were surprised that I wasn’t studying music. Eventually I realized I should do that. I remember thinking that the world doesn’t really need another bored science teacher. It’s much nicer to have people who are passionate about what they’re doing, especially music.”

Brian followed his devotion to music, and managed to pass it on to his children, with plenty of support from Jenn along the way. A dozen or so years ago, Brian and first Liam and then the other two children began playing at Renaissance festivals all over New England. Jenn would stay home with whichever child was busy with soccer practice, figure skating, or the Minnesingers. They play a lot of Celtic music, Brian says.

“I remember working hard to try to encourage them without feeling like they were being forced into it. Instruments would always be available, conveniently,” Brian laughs. “I always tried to make musical experiences joyful. Liam grew up with music, and played violin with the Island strings program. He played cello for Nancy Jephcote for 10 years, and he played with me whenever I asked. I remember I had a gig to play at the Wharf, and he’d been playing with me at home for a long time and I needed a bass player, so I brought him when he was 10 years old, which is kind of crazy. Around that same time we started a Renaissance festival act. He’s been part of the groups I play in for years.” 

Nowadays Liam is assistant engineer at Larrabee Studios in North Hollywood, a job he was well prepared for after graduating from Berklee College of Music. He earned a scholarship, and while Brian suggested the scholarship meant he could go to any school, Berklee is what Liam wanted. 

“I did say, Well yes, you could go to Berklee, but you could go to another school,” Brian said. “He had the right to follow the dreams that he’s earned, and I’m very proud of him.”

Liam says “growing up Weiland” meant that music was an inescapable part of day-to-day life. 

“I still love to get together with my family and play,” Liam wrote in a text. “I now live on the opposite side of the country, so it is much more difficult to do, but when I’m home I love to play and perform with my family whenever possible.”

COVID threw a wrench in visiting this past year, but Brian says he hopes to visit Liam this summer. 

Avalon graduated from MVRHS in 2020, another strange, pandemic-fraught year. She decided to travel rather than jumping into more remote learning at college right away. After spending close to a year living on and around Oahu in the Hawaiian Islands, Avalon is back home for the time being. Her instrument of choice is the harp, although she enjoys other creative outlets besides music. 

“In high school I discovered my love for ceramics,” Avalon says. “I’ve always considered myself more of an artist than a musician. I plan to continue to study ceramics in the coming years as I enter the world of college. Since leaving the Vineyard and coming back home, I’ve gained a new appreciation for the Island and music in my family — one that was hard to have when Martha’s Vineyard and this small life was all I’d ever known.” 

Avalon said she loves that she was surrounded by love and music growing up. “Growing up Weiland was and is so special,” she says. “I had an extremely unique, love-based, and music-filled childhood. I’ve played many different instruments over the years, but mostly the harp. Throughout my musical upbringing, I was on the stage a lot. As a family we played tons of shows, benefits, weddings, and any kind of event where there could be music.”

While growing up with music always around, it sometimes felt like a lot, she admitted, but now she’s looking forward to getting her harp out again. “I’m not sure I’ll ever get back to performing, but playing music will always be part of the Weiland family, and it will always be a part of me.”

While Jenn has been the one to keep track of the schedule and who is going where, she does enjoy playing fiddle, calling herself “a perpetual beginner fiddler.” She says she’s ready to delve back into playing as well, but says it takes her a month to learn a song the rest of the family can pick up in an afternoon.

“I believe the best way I can support Brian and the kids as they continue to pursue music is to go with the flow and be a roadie whenever possible … haha!” Jenn wrote in an email. “Oh yes, and deliver snacks and forgotten instruments when they are performing locally.”

The youngest Weiland, Aiden, picked up the violin at age 4. “The older he gets the more he falls in love with musical theater,” Brian says about Aiden. “He was playing in the orchestra pit when he was 8 or so. As soon as he could, he wanted to be on the stage.” 

Aiden’s just back from the Minnesingers trip to Ireland, and he played a role in the recent high school production of “Les Misérables.” He and Brian played 66 live-streaming Facebook sessions when the pandemic began, because Brian wanted to be sure there was still music for students. Aiden is taking voice lessons locally as he pursues his own passion, supported by Jenn, Brian, and his brother and sister. The youngest Weiland has a practical head on his shoulders even as he follows his own dreams. 

“I find singing to be a new and exciting aspect of music in my life,” Aiden writes in an email. “I play both violin and fiddle, as they’re technically the same instrument. Fiddle is an informal way of referring to a violin, often in the context of genres such as folk or country music. I often think about whether I’d like to pursue something musical as a possible career path post–high school. The stability of a musical career raises concerns, but I certainly haven’t ruled out the possibility. Either way, I’m positive I’ll be continuing to do musical things for the rest of my life, whether or not they be in the form of a career.”

Brian said he and Jenn have talked to Aiden about what he might want to do when he “grows up,” but that he’s still young and has time to think of the possibilities. 

“He’s basically said he has no idea, he’s still young. But he also said, ‘I do have to ask where the revenue stream is with all this,’” Brian said with a chuckle. “I kind of wish we lived in a world where you didn’t have to ask that question to follow your passions, but we all have to pay the bills. I’m kind of glad he gets that point now.”

Growing up in a house filled with music has brought a lot of joy to the family, and it’s paved the way for their individual paths. Brian says he thinks if it were another time, Jenn might’ve wanted an even larger family, so that maybe there would be a doctor in the mix, someone who could take care of them as they got older: “We have a musician, an artist, and an actor … my wife says maybe that fourth child would’ve been the doctor, and I say, ‘No, that would’ve been the poet.’” 


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