Phish fans went gaga in 2013 when the Vermont jam-rockers dropped waves of stunning improvisation in a 37-minute “Tweezer.” Holly Bowling, a classically trained pianist who’d grown up on the Grateful Dead and seen Phish nearly 300 times, was at that Nevada show. But Bowling didn’t simply obsessively listen back to a recording. She painstakingly transcribed the “Tahoe Tweezer” for solo piano.

“That was the first time I’d kind of merged these two worlds,” says Bowling, 34, who at her husband’s urging posted a solo performance of the historic jam on YouTube, eliciting more than 100,000 views. “That number was a little higher than I anticipated, and that [clip] ended up being the doorway that opened for me.”

A Michigan native who lived in New Hampshire before moving to San Francisco, Bowling soon boosted her repertoire in the wake of offers to record and perform. She recorded Distillation of a Dream, a 2015 album of Phish songs that included a take on “Tahoe Tweezer,” and then the kindred 2016 Dead project Better Left Unsaid. She recasts songs from both bands in piano concerts that include a Sept. 15 date at City Winery. She’s also set to perform original songs at Brighton Music Hall on Nov. 16 with the promising jam-band Ghost Light, which she co-launched this year. Whether performing solo or with her comrades in Ghost Light, Bowling embraces taking risks.

Her solo work distills the music of bands that take similar risks, but with multiple instrumental and vocal parts that she pares down to piano. “I’m definitely drawn to some of the more complex compositions from both Phish and the Dead,” she says. “It’s an interesting puzzle. … The whole arranging process is about accuracy, but it’s also about what you choose to include and what you choose to leave out.”

She takes sonic liberties beyond the keys, plucking or using sticks on the piano strings in open-ended epics like the Dead’s “Dark Star,” in addition to stretching beyond her original arrangements. “At this point, I pretty rarely play the transcriptions,” says Bowling, who credits Brad Mehldau and Christopher O’Riley as inspirations for her approach. “There’s a lot more room for me to improvise and have each piece be a springboard for what I want to do at the piano.”

She’s been able to perform with the Dead’s Bob Weir and Phil Lesh and play her solo pieces for members of Phish. “Those guys have all been really cool,” she says. “I love this music and see [my work] as another way to explore and catch it in my own way.”

What she doesn’t do in her solo shows is sing. “I’m definitely singing the words in my head,” Bowling admits. “It’s really cool to let people hear the lyrics unfold in their minds when they hear the melody.” She describes her solo concerts as a more inward alternative to outwardly communal Dead or Phish shows. “It’s kind of contemplative, and this music has really strong emotional ties for a lot of people, so they can take it in and let it transport them.”

Bowling now gets her communal kicks with Ghost Light, where she joins—and sings with—guitarists Tom Hamilton (of Joe Russo’s Almost Dead) and his American Babies bandmate Raina Mullen, drummer Scotty Zwang (of Dopapod) and bassist Steve Lyons. “We went into the studio as a brand new band that had never played a show together and started working on songs and recording,” Bowling says. “There was definitely a bit of that element of ‘cross your fingers and see what happens.’ ” But while song choices for an album—as well as release plans—remain in flux, initial live sets prove Ghost Light has quickly forged a natural personality and knack for blending song craft (the tentatively titled “If You Want It” is a kinetic earworm) with free jamming.

“Everybody’s bringing really different stuff to the table, so it doesn’t have one flavor or one thing that the improvisational sections sound like,” says Bowling, who expands to electric keyboards in Ghost Light. “That kind of flexibility and unpredictability is something that really fires all of us up.” ◆

Holly Bowling plays City Winery on Sept. 15 and Brighton Music Hall with Ghost Light on Nov. 16.

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