Written By: Demetra Edwards & Elsie Gaw | Photography By: Kit Noble

When it comes to catching good tunes on Nantucket, it’s usually only a few steps away.


Guitarist / Vocalist

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Twenty-year-old Matthew Merritt hopes that performing on Nantucket’s cobblestone streets will eventually pave his way to the big time. Despite picking up guitar only three years ago, Merritt hasn’t wasted any time in taking his sounds to the streets. Whenever he gets time off from his valet job on Nantucket, Merritt can be found on the bottom of Main Street, strumming his acoustic and singing ballads like “Brown Eyed Girl.”

“Playing on Nantucket has been a good opportunity to practice playing in front of a lot of people since it’s usually so crowded in town whenever I’ve been out there,” Merritt says. “I would like to make enough money off of playing music to be able to live comfortably, while doing something that I enjoy.” So how much money can you make as a street performer on Nantucket? On a busy summer night, Merritt says he can make around $25 an hour. Of course, the experience alone is worth its weight in gold. Hopefully someday in gold records.


A Cappella

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For nineteen years, The Cobbletones have taken the stage at the bottom of Main Street where their harmony draws throngs of fans on summer nights. Legend has it that the the all-male a cappella group got its start when the original members couldn’t pay their tab at the Club Car. Instead of washing dishes, they took to the street to literally sing for their supper. The Cobbletones became an official group in 1997 thanks to island brothers, Caleb and Seth Wheldon.

In the years since, The Cobbletones have seen hundreds of alumni pass through their ranks. For many local Nantucketers, singing on the streets is a rite of passage. Past members include the likes of local triathlon star Beau Garufi, who was a member for four years, and budding professional musician Jacob Butler. One of their founders, Caleb Wheldon, now sings a cappella professionally in Boston.

Yet, most members consider singing a cappella a passion, not a profession. They all work other jobs throughout the summer. “We have been on the border between being a professional, legit group and just a couple of guys who want to have a great time,” says Will Wraith, the group’s business manager. “We’re not doing CDs or anything like that. We just genuinely love bringing our happy vibes to the community.”

The group’s history, however, hasn’t always been harmonious. In 2011, they ran into trouble with the police when they were kicked off of their spot at zero Main because crowds were overflowing into the street and disrupting car traffic. “There was outrage,” says Wraith. “Things got intense, but eventually people in town badgered the police long enough to let us come back to zero Main. The community banded together and said let them sing.” And that’s exactly what the Cobbletones continue to do.



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If you’ve ever taken an evening stroll down Main Street, you’ve most likely come across a neatly appointed man vigorously playing the fiddle outside of Ralph Lauren. Cast in the yellow street light with his foot keeping time, the fiddler looks like he stepped out of an English fairytale, which is not far off from the truth. Born in London, Bobby McGuire began studying music at the age of five. He first learned to play the violin, then the piano. By the age of 23, he was the organist at his local church. McGuire went on to graduate from Cambridge University with a degree in music.

Now twenty-nine, McGuire is a full- time musician, performing at various venues across Nantucket and spending a few evenings a week with his fiddle in town. His favorite venue is in the classic close quarters of the Starlight Theatre, where his Irish melodies make you wish you had a Guinness in hand. He begins each performance with his rendition of “Red Haired Boy,” immediately transporting his audience to a pub in Dublin.

When asked what advice he would give fellow aspiring musicians, McGuire says, “Keep making noise. The key for success is to just do it as much as you can. You can never predict what’s going to happen.” Indeed, from playing his fiddle in front of King’s College in London, to playing on the streets of Nantucket, Bobby McGuire knows how to make royal sound on both sides of the pond.



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At just fourteen years old, Phaedra Plank has already mastered the clarinet, the piano, the violin, the guitar, the ukulele and the musical saw. Performing at the Nantucket Community Music School during the school year and taking it to the streets last summer with her sister, Plank is no stranger to the Nantucket music world. Opting to go solo this summer, this bubbly teen and her whimsical ukulele make a harmonious match.

“I usually see if kids are around, and I will play upbeat songs,” says Plank, whose usual spot is on the corner between the Juice Bar and the Sunken Ship. “If adults are around, I usually play pop songs.” Entering her first year at Nantucket High School, Plank conducts more than just her musical career. By day, she sails and volunteers doing research on scallops. By night, she enters performance mode, though she admits that it can be a challenge. “Getting out for the first five minutes is hard,” she says of the mild stage fright she conquers each night. But once Plank begins playing, that fear is replaced with pure confidence. After all, she says, “It’s just so much fun to play and make a little money doing something you love.”

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