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When you have the pleasure of sifting through Kenny Chesney's expansive catalogue of songs, you'll find there are a small selection of places that emerge again and again.
There are, of course, the odes to Chesney's upbringing in Knoxville, Tennessee, and his tribute to the sunny, freeing shoes of the US Virgin Islands. But there's no question that Boston, Massachusetts, holds a uniquely special place in Chesney's heart.
It's where the ‘I Go Back’ hitmaker's summer tours would conclude year on year, with Chesney delivering a momentous three-show stint at the city's Gillette Stadium during his last stadium run in 2024 with Zac Brown Band and Megan Moroney.
It's where he describes the birthplace of his loyal fanbase, No Shoes Nation, as being back in 2012. And it's where Chesney sings so fondly about on his fan-favourite gem, ‘Boston’.
Such is the lore that surrounds that island-inspired anthem - which follows the story of a bartender in the US Virgin Islands who has moved away from her home on the East Coast - that Chesney has maintained he will only ever perform it in Boston.
It's a beautifully perceptive and immersive offering, with Chesney capturing the gentle defiance and joie-de-vivre that underpins this mysterious character's vibrant journey of independence. Throughout the album, he transports you to the hazy, easygoing afternoons spent at the Quiet Mon or to the sunset revelations received when viewing the world from the comfort of an Old Blue Chair on the beach. The album on which ‘Boston’ lives, Be As You Are, remains one of Chesney's cult classics, a project that fans often cite as feeling the most unmistakably “him”.
In his new book with Holly Gleason, HEART*LIFE*MUSIC, the five-time CMA and ACM Entertainer of the Year reveals the tale of ‘Boston’ was inspired by a real-life encounter.
He begins by recalling how the Be As You Are writing sessions began organically, before he even realised he was crafting a cohesive album. The project is intentionally pared-down and intimate, with Chesney eschewing his arena-sized hooks and galvanising, electric guitar riffs in favour of mellow, acoustic gems.
The ‘Just To Say We Did’ singer-songwriter shares that he quickly noticed a connection between the East Coast and his beloved Virgin Islands, “Starting in 1998, it seemed eight out of every ten girls I met in the Virgin Islands were from New England. Whether in the bars, in restaurants, or on boats, those accents you can't miss. Having some local friends, I could hang out and run into someone I knew”.
Chesney goes on, “I kept seeing this one bartender. She wore a Red Sox cap backward, and you could see she had these baby dreadlocks peeking out from under it. Didn't matter when or where I saw her, she always had that Boston cap on”.
It was these meetings that led to the kernel of the idea for ‘Boston’, “You never know why something strikes you. Someone's spark, a random detail catches your imagination...”
Chesney expands, “All that was whirling around my head one night when Mark Tamburino started playing this guitar part. It had a real groove, with a melody inside it that felt good”.
From this musical foundation, as Chesney hurtled down the highway on his tour-bus, the beginning of ‘Boston’s now-iconic hook began to take shape, “I was in my bunk thinking about that bartender, about a lot of stories I'd heard from a lot of my friends down there. That groove started circling around my head, the beats dropping just so...She wears a Red Sox cap...to hide her...baby...dreads...”
It's fascinating hearing the wonderfully casual and simple origins of a song that has since left such a lasting impact on so many fans, and has helped entrench Chesney's relationship with the city. It feels apt that ‘Boston’ appears on what remains, in many commentators’ eyes, Chesney's most personal album to date, Be As You Are.
While the spirit of the US Virgin Islands will always be laced into that project's DNA, and indeed much of Chesney's later work, his love for Boston still radiates fondly through.
We're hoping that, after his eagerly anticipated second Sphere Las Vegas residency this summer, Chesney will embark on another of his signature summer tours in 2027, concluding with a familial, celebratory run at Gillette Stadium. Because that means that, after two years without it, we'll get to enjoy ‘Boston’ live once again.
For the full lyrics to Kenny Chesney's ‘Boston’, see below:
“She comes from Boston, works at the jewelry store
Down in the harbor, where the ferries come to shore
She never really knew how good it would feel
To finally find herself in a place, so warm and real
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She wears a Red Sox cap to hide her baby dreads
The girl she was in New England, is different now and dead
In all the local bars, she flirts and tells the boys
While they're talking, she's from Boston
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She comes from Boston, talks to her family, now and then
Through e-mails and post-cards, she tries to explain to them
That education and occupation will have to wait for now
She loves the Rosta Reggae rhythms, her dreams have changed somehow
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She wears a Red Sox cap to hide her baby dreads
The girl she was in New England, is different now and dead
In all the local bars, she flirts and tells the boys
While they're talking, she's from Boston
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Her toes dig deep and deeper in the sand
She's seduced by the sunsets and her new life at hand
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She wears a Red Sox cap to hide her baby dreads
The girl she was in New England, is different now and dead
In all the local bars, she flirts and tells the boys
While they're talking, she's from Boston
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She wears a Red Sox cap to hide her baby dreads
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From Boston
She came to this island from Boston”
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