The singer-songwriter returns for back-to-back shows at The Guild in Menlo Park.

Palo Alto-raised singer-songwriter Molly Tuttle, who took home a Grammy for Best New Bluegrass Album, returns to the Bay Area to play The Guild April 1-2. Courtesy Samantha Muljat.

Although Molly Tuttle moved out of the Golden State more than a decade ago, the acclaimed musician will always be a California girl at heart – and in the hearts of her Peninsula family, friends and fans.

“People feel like I’m still a local,” she said during a recent interview from Nashville, Tennessee, where she’s lived for the past eight years following a stint in Boston attending the Berklee College of Music. “I still get that feeling like I’m coming home when I get to come play in the Bay Area.”

The Palo Alto-raised Tuttle and her band Golden Highway will be back for a pair of concerts at The Guild Theatre on April 1 and 2. Both shows are sold out, but there is a waitlist.

Her visit comes on the heels of her recent Grammy Award for Best Bluegrass Album, honoring last year’s “Crooked Tree,” and a high-profile Best New Artist nomination.

Calling the Grammy experience “pretty surreal,” Tuttle said the week leading up to the awards, held in Los Angeles, was a flurry of activity and exciting music-industry events culminating, of course, in that gratifying win. 

“To actually take home the bluegrass award was really validating,” she said. “It’s such an honor to be awarded that by my peers … it’s really affirming of what I’ve been doing.” 

Though she’s new to The Grammys, Tuttle is no stranger to accolades, as she’s racked up many honors over the years, from the likes of the International Bluegrass Music Association, the Americana Music Awards and the International Folk Music Awards. 

An astonishingly virtuosic instrumentalist (particularly on guitar), Tuttle is also a talented singer and songwriter, and “Crooked Tree,” her third full-length album, is the first that fully leans into her bluegrass background.

Jack Tuttle, left, practices with his daughter Molly Tuttle during a session in January 2010. Courtesy Don Feria.

The daughter of local bluegrass legend Jack Tuttle, a beloved Palo Alto music educator, she grew up performing both locally and internationally with her father and brothers. Bluegrass, to her, means music meant to be shared among family and friends, with a certain community spirit in addition to a recognizable sound. 

Acknowledging its roots in the southern United States, pioneered by Bill Monroe, “I think it’s always been a fluid thing since it was first created,” she said. “It’s really the spirit of simple music people can play together.” And, she noted, “there’s a lot of bluegrass that comes from California.” 

The final track on “Crooked Tree,” “Grass Valley,” evokes memories of the West Coast bluegrass community she grew up in, attending festivals and jam sessions with her family. Her California ties pop up in other parts of the album as well. In “San Francisco Blues,” she mourns for the Bay Area of the past, a time when artists and working families weren’t pushed out by rising rents and gentrification, and expresses a homesickness for both the Bay Area of her youth as well as the imagined one from long before she was born. Tuttle said she wished she could go back in time to see what Palo Alto was like in the 1960s, when her mother was growing up there. “She’s really seen it change,” she noted. 

The haunting song “Castilleja” was definitely not written about the private Palo Alto girls’ school, but Tuttle, a graduate of nearby Palo Alto High School, did first encounter the word (meaning a desert-blooming flower) thanks to the Old Palo Alto neighborhood campus.

Tuttle’s songs often reflect the beauty she finds in the natural world, and she has a special love for the coastal region between Half Moon Bay and Santa Cruz, where the redwoods and the Pacific Ocean are both within reach. “That’s my happy place,” she said. The album’s title track uses an arboreal metaphor to explore the challenges and benefits of not always fitting in. Tuttle co-wrote the song with her friend and fellow Bay Area artist Melody Walker. 

“Both of us kind of grew up feeling different from the other kids,” she said. Tuttle has the immune condition alopecia areata, and, at age 3, permanently lost all of her hair. “That was something that made me stand out,” she said, recalling the embarrassment and worry she felt as “a pretty shy kid,” masking the condition under hats and, later, wigs. As she grew older, though, she found a sense of community and acceptance, and has worked as an advocate and mentor with the National Alopecia Areata Foundation (an organization that meant a lot to her as a child). In “Crooked Tree,” she embraces not conforming to an expected mold.

The cover of “Crooked Tree,” album by Palo Alto-raised musician Molly Tuttle and Golden Highway. Courtesy Sacks & Co.

“Oh can’t you see? A crooked tree won’t fit into the mill machine. They’re left to grow wild and free. Oh I’d rather be a crooked tree,” she sings. Feeling different, it turns out, can also be something many of us have in common. 

“I wrote that song out of my own experience of feeling like I had something that made me different,” she said, “but it’s really for everyone, because I feel like we all have something like that.”

Though her music is steeped in bluegrass traditions, Tuttle’s never been one to be pinned down to just one genre, and enjoys exploring other sounds and styles. “I love going back to my bluegrass roots,” she said. “I could see going off and doing something different as well.” 

The “Crooked Tree” album was recorded with Tuttle’s band, Golden Highway, which includes mandolinist Dominick Leslie, banjoist Kyle Tuttle, fiddle player Bronwyn Keith-Hynes and bassist Shelby Means. They will be joining her at her local shows – and for the foreseeable future. 

“We’ve been having such a great time on the road; I want to keep it going for as long as I can,” she said. Coming up, she’ll be busy with a slew of tour dates across the country, including summer gigs with Dierks Bentley and, in September, an appearance at acoustic-guitar icon Tommy Emmanuel’s Nashville guitar camp. But before that, she’s looking forward to her April homecoming.

“I’m really happy that The Guild exists,” she said of the former movie theater-turned-performance space. “It’s so nice to have a venue that size in Menlo Park.” 

Coming back to the Peninsula to perform “used to make me a little more nervous,” she said, “now I feel a little more free to talk about growing up, where I went to school, my favorite places … it’s a really good feeling to come back.” 

At last year’s Guild performance, she brought her dad up to play, and she’s likely to call on some special guests again. “I haven’t started asking people yet – that’s a good reminder!’ she laughed. “I hope to see a lot of old friends and maybe make some new friends.” 

Molly Tuttle and Golden Highways performs at The Guild Theatre, 949 El Camino Real, Menlo Park, on Saturday, April 1, and Sunday, April 2, at 8 p.m. Both shows have a waitlist (tickets are $48-$88). More information is available at and

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