Yes, that James Taylor.
You might see him waiting in line at the coffee shop, picking up groceries, or biking along back roads. Of course, you’ll definitely see him at Tanglewood, where he’s performed for decades to sold-out crowds under the summer sky.
Visitors to the Berkshires often ask us: Why Lenox? Why does a five-time Grammy-winning artist—someone who could live anywhere—choose this tiny town of fewer than 5,000 people? Turns out, there are lots of reasons. And many of them are the same ones our guests fall in love with when they stay here.
A Life Rooted in the Berkshires
One clue comes straight from the lyrics of “Sweet Baby James”:
“Now the first of December was covered with snow
And so was the turnpike from Stockbridge to Boston
Though the Berkshires seemed dreamlike on account of that frosting…”
It’s more than a poetic line—James Taylor has a real connection to this region. His first show in the Berkshires was at the old Music Inn in 1970. Even then, he knew that this place was special. “…it had the advantage of being a Berkshires audience, which is very savvy but relaxed,” Taylor said. “They pick up what you are putting down. That’s the thing. You want a smart audience.”
It stuck with him. Years later, when Taylor and his wife Kim had twin boys in 2002, they looked for a place to raise their family. After trying out a few other options, they settled in Lenox—for good.
Photo Courtesy of BSO Press Office
A Great Place to Be at Home
In a 2024 interview with Berkshire Magazine, Taylor put it beautifully:
“A lot of people who’ve traveled a lot in the world for a long period of time have decided that the Berkshires is the place. I don’t know why that is. I think it’s energy from Boston and from New York. And the finger of the Green Mountains that reaches down into Massachusetts and is the Berkshire Hills. It’s like a route to essential New England, Vermont, New Hampshire, Quebec, and the Adirondacks. That’s what it is geographically, and it has as much history as you can hope for. It also has the cosmopolitan energy of Boston and New York that has always fed it. You feel the cultural roots in dance and the theater and the music that’s up here, and the museums. And the people here—we say it over and over again—they’re the people you want to be with.”
It’s not just about scenic beauty (though there’s plenty of that). It’s the rhythm of life here. The blend of creativity, community, and culture.
Photo Courtesy of BSO Press Office
Music, Meaning, and Giving Back
Since 1974, James Taylor has made Tanglewood his musical home base, performing his 52nd and 53rd concerts there in 2024. His very first Tanglewood appearance—alongside Linda Ronstadt—drew 15,000 people when the lawn was only half the size it is today. In 2002, a show with John Williams drew 24,000, prompting Tanglewood to set a permanent 18,000-person cap on attendance.
“I’m not gonna let go of Tanglewood,” he says. “When I stop doing it, it’s gonna be because I am retiring.”
Taylor’s love for the Berkshires extends well beyond the stage. After the 2010 Haiti earthquake, he and Kim organized a benefit concert at the Mahaiwe Theater in Great Barrington. Within a week, two sold-out shows raised over $600,000 in aid.
Explore the Best of Lenox from Hampton Terrace
There’s a reason people from around the world flock to Lenox—and why so many return. World-class performances at Tanglewood. Art at The Mount and MASS MoCA. Moments of stillness in the hills and trails. The energy here is vibrant but unhurried.
Taylor says it best:
“This is a great place to be at home.”
And for those just passing through—it’s a great place to stay awhile.
At Hampton Terrace, we’re just minutes from Tanglewood and steps from downtown Lenox. Our inn has hosted guests for over a century, and we continue that tradition with modern comfort, Southern charm, and some of the highest guest ratings in the region (5.0 on TripAdvisor, 4.9 on Google).
Book Your Stay Today
Ready to experience the Berkshires like a local? Whether you’re planning a summer getaway around Tanglewood, a romantic weekend, or a cultural escape, Hampton Terrace Inn is your perfect home base in Lenox. Don’t wait—rooms fill quickly during concert season.
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