By Amy Conway
Current portraits by Megan Haley
Family photos courtesy of the Taylor family

“The smell of the dirt floor in the Shed during a show—that’s a very strong memory for me,” said Rufus Taylor. As Proustian experiences go, it’s probably rare. But Rufus and his twin brother, Henry, know the Koussevitzky Shed—Tanglewood’s famed open-air performance space—much better than most.

Their father is James Taylor, the legendary singer-songwriter who will perform again at Tanglewood on July 3 and July 4. Their mother, Caroline (Kim) Taylor, worked for the BSO as a senior advisor, later becoming a trustee. A writer and musician, she often joins James in concert. Rufus and Henry, now 24, grew up just down the road and spent countless hours on campus, both backstage with their parents and running around on the greens. Their unique Berkshire upbringing—surrounded by nature and music, and largely insulated from the trappings of fame—has shaped who they are today.

“We live on top of a hill, surrounded by forests,” said Henry. “Having the freedom to just explore in nature, go outside and have fun, that’s a big part of what the Berkshires means to me.”

This summer, Rufus plans to thru-hike the Appalachian Trail southbound from Maine to Georgia—90 of its 2,000-plus miles run right through the Berkshires. Henry, a gifted guitarist, is touring as a backing vocalist and band member for James Taylor & His All-Star Band. This is Henry’s fourth tour with the group (the first was in 2022–23 with Jackson Browne and his father).

The brothers have an easy way about them, joking around with clear affection. You’d never guess that, as Rufus joked, “we almost killed each other for the first 12 years.”

They attended Berkshire Country Day School through ninth grade, and Rufus credits the experience with launching his love of academia. “The teachers are really, really engaged and thoughtful. I’ve never studied under people who cared so much about education,” he said. Henry appreciated the emphasis on studying science through exploring the outdoors and has fond memories of Ski Fridays—the tradition of school ending early so kids could head to Butternut or Bousquet.

By the time they graduated from BCD with their class of 14, the twins were ready for space apart. Milton Academy near Boston was a bigger pond. “We could find our own interests. We weren’t overlapping and we didn’t have to be competitive,” Henry said. Rufus went on to attend Amherst College, studying psychology and religion, and graduated in December 2024. Henry transferred from Williams College to Berklee College of Music in Boston, where he’s studying songwriting and may add classes in music business and production. They both now have apartments in Boston.

Genuinely curious, Rufus asks his brother: How does the experience of playing with their dad differ from projects he does at Berklee, with his peers? “There’s a pretty laid-back vibe compared to other bands and touring acts on Dad’s level,” Henry said, “but it’s still very professional. With a new arrangement of a song, my dad and Jimmy Johnson, the bass player, will conduct their way through it and get all the parts tight. We’ll focus on strings, percussion, and background vocals. It’s well considered, and it flows very efficiently.”

Henry knows the experience is special: “It’s an amazing privilege to learn from some of the best. Everybody’s very kind and accommodating and willing to play and experiment.” But the training isn’t what means the most. “We’ve been at boarding school and then in college, so we’ve spent a lot of time apart. It’s a great privilege to spend three months with my dad—in hotel rooms or tour buses, watching TV shows or playing cards. What I appreciate the most on the road is just having time with my dad.”

That closeness didn’t happen by accident. “Our parents have a lot going on in their lives,” Henry said. “But they’ve always been parents first. They tried to make our childhood as normal as possible.” Being in the Berkshires was part of that. “Things could have played out really differently if we were growing up in New York or L.A.,” Rufus added. “One of the lovely things about the Berkshires is that none of that really exists here. It’s just all very grounded.”

It was only later that they realized their musical upbringing wasn’t typical. Rufus recalls hearing the birthday song harmonized by different family members. Or memories like, “Dad running around with an electric toothbrush going ‘mmm, mmm, mi mi,’ looking for a piano to figure out what note it was making.”

World-class musicians were a regular part of their lives, though the boys didn’t think of them that way. “You look back and you go, ‘that’s the best cellist in the world,’” Rufus said. “But Yo-Yo Ma is just a normal sweet guy that cracks jokes and is good with kids.”

Having grown up at Tanglewood and now playing music professionally, “it’s a trip to be on stage at the Shed, to look out from that perspective,” Henry said. “Acoustically, it’s amazing. And there’s something special about playing to a home crowd, to people who love Tanglewood and the Berkshires as much as you do. But it’s also sort of nerve-wracking. I’m more conscious about how people are receiving the performance, because you’re not just leaving the next day—you live there.”

For his part, Rufus is considering a master’s degree in social work or psychology, or pursuing regenerative agriculture. “I care a lot about food sovereignty, making sure communities have access and control over the food that they have,” he said. He sees good work happening in Western Mass and could imagine settling in the Berkshires: “If I can get my partner here—he’s very attached to Boston.” The two met while Rufus was at Amherst and his partner was at UMass Amherst. They both play on the Boston Ironsides, an inclusive rugby team that is part of IGR, International Gay Rugby. “It’s a really great part of my life,” Rufus said.

Before graduate school or settling down anywhere, though, Rufus has a trip to take. He plans a thru-hike of the Appalachian Trail, starting in Maine and heading south to Georgia. Though he’s hiking solo, friends—and Henry—will join him for sections. “A thru-hike has been a lifelong goal,” Rufus said. “And in terms of where, it’s always been the Appalachian Trail. Because, you know, that’s where we’re from.”