Bringing music into Vineyard Haven

Live music has long been central to Island life, from the legendary Hot Tin Roof, where Carly Simon — who co-founded and co-owned the venue — performed alongside other notable names including Lou Reed to karaoke nights at the Ritz Café in Oak Bluffs, the Island music scene is, and has always been, wide and varied. In recent years, Vineyard Haven, once a dry town, has emerged as a vibrant new hub for live music.

Although live music is actively becoming more prevalent in Vineyard Haven, the town is also home to one of the oldest bands on the Island. Founded in 1868, the Vineyard Haven Band regularly performs in Owen Park. Now celebrating its 150th anniversary, the band is the oldest continuous nonprofit cultural organization on Martha’s Vineyard. Its repertoire ranges from patriotic marches to contemporary fare, performed at summer staples like Illumination Night, the Fourth of July, and the end-of-summer fireworks. The band represents the Island’s long-standing music tradition. 

More recently, in 2016 Vineyard Haven became home to First Friday. The event transforms the town’s harborfront and Main Street into a hub of activity, with live music, local art displays, food trucks, artisan vendors, and family-friendly activities. 

Andy Herr is the guru behind all things music at First Friday. He is a producer and sound engineer, as well as a musician himself. “The vibe is always a bit different,” said Herr; “at the same time, there is a core intergenerational group, even in the summer. It’s an event among events in the summer that is very well-attended by Islanders and their families.” 

In its early days, First Friday featured solo performers tucked among artists’ tables. Post-COVID, Herr and his team reimagined the setup, shifting performances from the Owen Park bandstand to the beach — and memorably, in 2021, to a floating barge. The event now draws teens and young adults for its popular silent disco, presented by Pathway Arts, which kicks off after the live music is over. “One of the big successes of the event is bringing multiple generations together,” Herr said.

Herr sees First Friday as more than entertainment: It’s about community. “With everything happening on the federal scale and nationally, small communities like this are one of the most important things we can possibly cling onto and build upon,” said Herr. 

“People have all different reasons for listening to music, and part of it is just feeling a sense of belonging and kinship with the human race. Everyone has a certain social need, even the most introverted of us,” added Herr. “Going to listen to live music is a really easy and approachable way to get that, and if it’s right, it can be really a total mood changer, and have possible ripples in their lives and in everyone they interact with.”

Beyond First Friday, Herr has kept Vineyard Haven buzzing with music through Open Mic Nights at Island Music, which he has hosted for more than eight years. Herr explained that there is a core group of regulars who attend these open mics, but in the summer, the evenings are dominated by walk-in visitors who often bring very special talents to share. 

In the off-season, attendance is still high at Open Mic Night, and many people who have recently moved to the Island attend the event looking for a musical community as well as a space to share their talent. “Even in the off-season, I have consistently seen the store full,” said Herr. 

One musician of note is Delanie Pickering, who began attending Open Mic Nights when she first arrived almost a decade ago, sharing her blues with the local community. Pickering now plays with Johnny Hoy and the Bluefish. 

Herr is also a board member of the Vineyard Haven Harbor Cultural District, and he shared that the board is hoping to take over booking at the Katharine Cornell Theatre in order to get more live music in that space.

“Slowly, more places are hosting live music, and I’m encouraged to see that. Part of it has to do with the fact that there are bars in town now,” said Herr. 

Regarding his own musical career, Herr said he plays a little bit of a lot of instruments. He started lessons when he was 3, doing classical piano, followed by guitar, alto saxophone, and string bass. Now he plays and teaches a variety of instruments at his music studio directly under the old Stone Bank that is now recently opened as the Ocean Club at the end of Main Street. 

“I hope people walk away with a song in their head,” said Herr about live music events. “I hope they had a good time.” 

Also providing a venue for local artists is the Martha’s Vineyard Sound Festival, an annual event that takes place at the end of August at Cove Golf & Grill, 386 State Road. This year it will feature performances by reggae legend Barrington Levy, and local bands and musicians including Sarah Shaw Dawson, Dock Street Fight Club, and WIlly Mason, as well as live DJ sets. 

With artisan vendors, delicious eats, and fun activities for all ages, the festival serves as a fitting capstone to the summer, inviting both Islanders and visitors to enjoy creative expression and togetherness on the Island. Each year, the festival features a musical mashup of genres — reggae, rock, soul, and more — delivering a rich and varied lineup meant to appeal to a broad audience. 

Phil daRosa is the co-producer of M.V. Soundfest along with his partner, Carter Hakala. He started it back in 2014, and it has grown from a series of shows into the festival that has now been taking place at the Cove for the past five years. DaRosa described the event as a passion project, showcasing local art and providing a space for Islanders to reunite after a busy summer. 

“We were happening at the same time as Beach Road, and since that left, it sort of left a hole for people with the desire to see live music –– and in an odd way, that helped the smaller events pick up the slack,” said daRosa. 

“Our festival is locally grown,” he continued. “The whole idea is basic, to showcase all of the talent on Martha’s Vineyard, as much as we can every year, and have that support an internationally touring act, which this year is Barrington Levy.”

Not only is the lineup almost entirely local talent, the audience is predominantly Islanders as well: “It’s mostly a local attendance, which is great –– that’s what we are hoping for, because a lot of people who live here, we don’t get to see each other that much in the summer. The past couple years, as this has been growing, everyone shows up to put a cap on the summer and get some time together. Carter and I just want to throw a party for all our friends, and bring in acts that we love.” 

DaRosa referenced the history of music on the Island, namely the Hot Tin Roof, which was a staple of the summer, describing this festival as an homage to how that history has changed. 

“That whole era was so special,” said daRosa. “Bonnie Raitt, Peter Tosh, just so many people played on that stage. That was a real place where you could see nationally touring or global acts, especially back in the early ’80s or late ’70s.”

“That paved the way for this really cool opportunity for those types of acts to come play in a small and intimate venue with a really appreciative audience –– that’s rare,” said daRosa. “There’s a new era now, where we’re trying to figure out how to fill that void.”

MV Soundfest is daRosa’s effort to help address that live music void felt across the Island. “It’s not a reggae festival, it’s an eclectic mix of artists and genres, so musically speaking, there’s something for everybody,” said daRosa, emphasizing the importance of the need for community events. 

“Considering how divided everybody seems to be these days, I think that having any opportunity to get together and just appreciate something, whether you’re right, left, straight, gay, whatever race you are, everyone can get together around music,” said doRosa. “You might have totally different viewpoints politically, but we might have the same favorite band. You can get together with anybody and appreciate art without conflict.” 

Vineyard Haven will continue to grow as a space for live music, bringing together community members and strengthening the bond of the town.The Black Dog Tavern & Cafe host live music, and M.V. Tap is looking to do the same. 

Tickets for Martha’s Vineyard Sound are still on sale! Buy them at marthasvineyardsound.com.