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The Castle Theatre Welcomes
Molly Tuttle - The Highway Knows Tour
🗓 Tuesday, November 18th, 2025
⏰ Doors: 6:30pm | Show: 7:30pm
➡️ 18+. Minors Welcome with parent or guardian
On the heels of two Grammy-winning albums in succession, with her band Golden Highway—2022’s Crooked Tree and 2023’s City of Gold—plus a nomination for Best New Artist, Molly Tuttle returns with a solo album that’s her most dazzling to date: So Long Little Miss Sunshine.
Recorded in Nashville with producer Jay Joyce (Orville Peck, Miranda Lambert, Lainey Wilson, Eric Church, Cage the Elephant), the fifth full album from the California-born, Nashville-based singer, songwriter, and virtuoso guitarist features twelve new songs—eleven originals and one highly unexpected cover of Icona Pop and Charli xcx’s “I Love It.”
Tuttle’s career, which began at age fifteen, has charted a course between honoring bluegrass and stretching its boundaries. On this album—a hybrid of pop, country, rock, and flat-picking, plus one murder ballad—she goes to a whole new place. Her stunning guitar work is more up-front on this album than ever before. (One of the most decorated female guitarist alive, Tuttle was the first woman to win the prestigious International Bluegrass Music Award’s Guitar Player of the Year in 2017, at age twenty-four, and won again the following year, with nominations nearly every year since; she has also won Americana Music Association’s Instrumentalist of the Year award.) So Long Little Miss Sunshine also features Tuttle playing banjo, something she’s never done on one of her albums before.
“I like to be a bit of a chameleon with my music,” she says. “Keep people guessing and keep it full of surprises.”
Tuttle has been slowly building this collection of songs over the last five years, while also writing and releasing two hugely successful albums and a six-song EP (last year’s Into the Wild) and playing more than 100 shows each year with Golden Highway. Along the way she’d send songs to Joyce, who she first started talking to about collaborating on the album a few years ago.
“I’ve been wanting to make this record for such a long time. Part of me was scared to do such a big departure, and that went into the album title So Long Little Miss Sunshine. It’s like, ‘You know what? I’m just not going to care what people think. I’m going to do what I want.’”
The album was recorded with a group of musicians that includes drummer/percussionists Jay Bellerose and Fred Eltringham, bassist Byron House, and Joyce on multiple instruments. Ketch Secor (Old Crow Medicine Show) also plays banjo, fiddle, and harmonica, as well as singing harmony.
Tuttle also conceived the artwork for So Long Little Miss Sunshine, which features multiple Mollys, each wearing a different wig except for one with nothing on her head at all. (“I probably own as many wigs as I own guitars,” she says.) Tuttle has been bald since she was three years old due to the autoimmune condition alopecia areata; she acts as a spokesperson for the National Alopecia Areata Foundation.
“I love raising awareness,” she says. “I talk about it onstage a lot and broaden it to include anyone who’s ever had something that makes them stick out and look or feel different from others. Playing my song ‘Crooked Tree’ live is very meaningful to me, because it’s a moment where sometimes I’ll take off my wig and talk about my struggles with self-acceptance.”
One album track, “Old Me (New Wig),” is “about leaving all these things behind that don’t serve you anymore,” she says. “Parts of yourself that really aren’t in your best interest, like low self-esteem, anxieties, and not feeling confident. Learning to own these different aspects of my personality but not letting them control me is another theme of the record that inspired the album title and the cover art. Those are all things I’ve struggled with through the years—just feeling like an impostor, like I wasn’t good enough. I like singing this song because there are days when I still have to tell myself to leave that stuff behind.’”
Most of the So Long Little Miss Sunshine songs were co-written with Secor, who is also Tuttle’s partner. “We spend so much time together, we live together, and anytime I have a song idea, or he has one, it’s just so easy to transition from whatever we’re doing into writing a song.”
Although they were written in different times and circumstances, Tuttle found to her surprise that the songs were all tied together by interwoven themes. The opening track, “Everything Burns”—a dark, intense, big-guitar song—was written in 2020, during the chaos and division of the start of the Covid pandemic. It might as easily refer to the current chaos and division in America since Election Day 2024, though. In fact, they recorded it the day after the election.
There are several songs about traveling—sometimes down the open road, like “Highway Knows” and “Oasis”—but also back in time, as on “Easy” and “Golden State of Mind.”
The record also tells “a kind of coming-of-age story,” Tuttle says. “‘Golden State of Mind’ is one of the songs I feel is a through-line to that. It makes me think about people I’ve been close to in the past that I’ve drifted away from, and about growing up and figuring out who you are.”
That theme is in turn picked up in the beautiful ballad “No Regrets,” one of the last songs Tuttle wrote for the album. “It’s about looking back on your life and thinking, ‘Well, maybe I could have done things differently, but if I hadn’t made certain mistakes or gone down certain roads, then I wouldn't be here.’ And I really like where I am now!”
So Long Little Miss Sunshine closes, as her last two albums did, with an autobiographical song, “Story of My So-Called Life.” “This is me looking back on my life, from growing up to going to school in Boston to moving to Nashville to where I am now—taking stock of all these pivotal moments throughout my life that made me who I am. I feel like after I’ve said so much in all the other songs, it’s just kind of nice to end it on a note of, ‘Here’s how this all came to be,’” she says.
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Earlier this year, Tuttle played guitar and sang on Ringo Starr’s new country album, Look Up. She also played with him and a host of other stellar musical guests at Nashville’s Ryman Auditorium and Grand Ole Opry as part of his televised Ringo & Friends shows. She was inspired by his fearlessness in following his passion for country music. “It is cool to see someone like that who has done everything you could imagine doing in a music career and he’s still just so psyched and still has a list of things that he wants to accomplish,” Tuttle says.
Looking back on her own career, Tuttle admits that she also has pursued what interests her: “It has never been a cookie-cutter thing where I’m just going down a straight road. I always had this crooked path.”