Singer-songwriters with Island ties debuted new music and lulled the audience with familiar tunes for a cause on Friday night: a benefit for elder locals to raise money for their continued care and self-sufficiency.
Around 350 tickets were sold for attendance to the show, called the “Songwriters for Island Elder Housing,” the third in an annual concert series where ticket proceeds directly benefit amenities for elder housing on the Island.
Friday’s lineup was rife with talent and experience, with many of the musicians being longtime friends. The event was organized by Jemima James, a caregiver and board member at Island Elder Housing (IEH), and advocate for affordable, independent living for elders. The father of her children, former husband and friend Michael Mason, was a resident of the IEH units before he passed away a few years ago. James said the housing and care he received was paramount to his own — and their family’s — comfort and happiness for those last few years.
“Island Elder Housing has meant a lot to me,” James said. “This [concert] brings some new light to it.”
Now she continues to spread that message and raises money for IEH through music. “We have the best of the local, Island-grown talent,” she said excitedly.
The lineup was locally-star-studded for Friday’s show. Other featured artists included James’ son, Willy Mason, as well as Jessie Pinnick, Lexie Roth, Lilah Larson, Nina Violet, Elisha Weisner, Kit Orion, Colin Ruel, Caroline Sky, and Isaac Taylor.
James herself is a celebrated musician who has performed for decades, released albums like her most recent in 2024, “Silver and Gold,” and has held audiences captive with her calming, yet strong voice, folk sound, and storied lyrics.
And the other musicians — who all sang one by one in a semi-circle on the Tabernacle stage in Oak Bluffs — harmonized with one another’s songs, joined together, and spoke to the importance of the cause they sang for.
“We can’t know where we’re going if we don’t know where we’ve been,” one of the nights’ musicians, Isaac Taylor, said in an interview with The Times before showcasing his deeply emotive vocals. “I just feel like honoring and supporting the elderly is of vital importance, because they are the foundation of our community.”
Spread out across three towns and four campuses, IEH provides 165 affordable units for low-income elderly and disabled locals. They handle most components of the organization, but for additions like electric generators, they need to raise the money externally.
“When we fundraise, it’s for the residents,” the executive director of IEH, Dorothy Young, said.
Each benefit concert over the past three years has been to raise money for generators in each elder housing complex, so the communities are never without electricity in the case of blackouts. The cost for these generators is close to a million dollars — and although they received a $50,000 grant for one automatic generator so far, they need much more to reach their multiple units. After an emergency blackout a few years ago showed IEH that residents were in dire need of generators to keep the power on, these benefit concerts were introduced by James as a way to bridge that financial gap.
State Rep. Thomas Moakley attended the show and spoke to the crowd during intermission. He voiced his support for IEH and their residents.
“This is not just about keeping the lights on,” he said. “Martha’s Vineyard is a community that sees a need and fills a need.”
IEH board member Cole Powers echoed the same sentiments, pointing out the benefit of services for Islanders of all ages, and the strength of a community that supports those in need of care and kindness.
“We need to help support our elders in every way we possibly can,” Powers said. “What does it say if we are a community that does not support its youth, elders, weak, and sick? Not much. And that’s not the Island community.”
The performances were a powerful backdrop to IEH’s message. Each musician sang two songs — mainly their own music, with only one or two covers throughout the night.
Lilah Larson, who lives and performs in New York and the Island, showcased a punk rock influence with their singer-songwriter originals. Their voice was emotive and rich with a raspy edge. They were immediately followed by born-and-raised Island musician Nina Violet, who alternated between a guitar and violin throughout the night.
Violet’s voice was commanding, ethereal, and familiar for many audience members who used to frequent her performances before she moved to San Francisco. Her original songs were a storyteller’s journey, rooted in inward investigation and metaphor.
Jessie Pinnick debuted a never-before-heard original about a woman named Julia who went on a journey of self-discovery. Her lilting and lovely voice strung the phrases and the lines together, captivating the audience and the other musicians beside her.
And Lexie Roth followed — her voice astoundingly soft and comforting in clarity — with an original of her own, which ebbed and flowed with harmonies from the other musicians.
In addition to a stirring performance of a tune called “Wrong Again,” written by Michael Mason, James and Willy Mason also performed a song that was written specifically for the occasion by James and Colin Ruel.
“I’m really happy that we have this reason to come together — to play music with new and old friends,” Mason said in an interview before the show.
Some of the newcomers of the night included Kit Orion, a Cambridge-based duo headed by Caitlyn O’Brien along with a bassist accompaniment. Their music explored themes of loss, mental health, and self-discovery, and O’Brien’s vocals were a soft place to land for the intense themes in the lyrics.
And Caroline Sky — who has volunteered for Camp Jabberwocky for more than a decade — lives in New York, has competed on “The Voice,” and “American Idol,” and sung with international musical legends. She sang an original, called “Giving Tree,” and stunned the crowd with her vocal jumps and runs.
Elisha Weisner, an acoustic guitar maker in Chilmark, debuted originals with an indie feel and tenor tone — and said he recognized the housing issues on the Island, and felt great about donating his time and music to benefit IEH. “It’s such a bonus that this is for a great cause,” he said.
From Ruel’s raw lyrics and deep tone to Mason and the Alpha Gals’ (a duo made up of Pinnick and Roth) hauntingly beautiful three-part harmonies, audience members were enthralled, tears fell, and standing ovations closed out the night.
“You need people with a lot of heart to make things like this happen,” the director of programming at the Martha’s Vineyard Museum, Laurel Redington Whitaker, said in a speech to the crowd. She then addressed the musicians on the stage behind her: “They’re all playing from their hearts.”
