Sierra Ferrell and her band rolled into the tropical charm of the Saint Augustine Amphitheatre on Florida’s east coast Friday night, bringing her Shoot for the Moon tour to a capacity crowd that was more than ready to sing along.

The stop came just two days after Ferrell picked up her second consecutive Artist of the Year award at the Americana Music Association ceremony at Nashville’s fabled Ryman Auditorium. At this point, Sierra may need a bigger trophy case—she’s also a four-time Grammy winner for her 2024 masterpiece Trail of Flowers—and just this week she was added to the 40th Farm Aid lineup in Minneapolis at the invitation of Lukas Nelson.

The Saint Augustine set leaned heavily on tracks from Trail of Flowers and her breakthrough Long Time Coming. The show burst open with “I Could Drive You Crazy” and “I’ll Come Off the Mountain”, followed by the wistful “Jeremiah” and the haunting “Bells of Every Chapel.”

The latter, famously inspired by a line from The Crown and featuring Billy Strings on the studio version, earned huge applause from the crowd. Later, “Silver Dollar” and the gypsy-jazz firecracker “Far Away Across the Sea” showcased her knack for weaving vintage styles into something fresh and magnetic.

Highlights of the Night

• “Whispering Waltz” – Sierra’s vocals soared with a tenderness that froze the crowd in place.

• “Lonesome Feeling” – A traditional acoustic cover of the Osborne Brothers’ classic, complete with spot-on banjo, mandolin, and fiddle breaks, transporting the audience back to the golden age of bluegrass.

• “Rosemary” – Performed solo and acoustic, one of the most intimate moments of the show.

• “Years” – The John Anderson cover became a powerhouse showcase for Sierra’s raw, passionate delivery.

• “Dollar Bill Bar” – Opener Nikki Lane joined Sierra to reprise her vocal role from Trail of Flowers, lighting up the stage with effortless chemistry.

• Encore: “Me & Bobby McGee” – The Kris Kristofferson classic ended the night with a raucous singalong.

Ferrell’s story is as fascinating as her music. A West Virginia native who once hopped trains and busked in Seattle, New Orleans, and Asheville, she now commands some of the biggest stages in Americana.

Her sound is a wild cocktail—old-time country, gypsy jazz, ragtime, folk, bluegrass—all filtered through a voice that feels like it belongs to another century yet speaks directly to today.

The crowd reflected that devotion. Many arrived in floral headpieces in her signature style, ready to harmonize on every chorus. When Sierra cued up “American Dreaming,” she asked the audience to sing along. There was no coaxing, no “one more time” ritual. From the very first note, the chorus roared back—proof of the unshakable bond between artist and fans.

Before Sierra took the stage, Nikki Lane warmed up the amphitheatre with her blend of honky-tonk swagger and retro-country soul. Her performance of the heartbreaking “Woodruff City Limit” was a standout, showing why she too is rapidly building a fiercely loyal following.

Together, Lane and Ferrell were a one-two punch of modern Americana—two artists rewriting the rules while paying homage to the roots. Catch them both if you can.

Sierra Ferrell – Saint Augustine Amphitheatre, FL
Shoot for the Moon Tour

• I Could Drive You Crazy

• I’ll Come Off the Mountain

• Jeremiah

• Bells of Every Chapel

• Silver Dollar

• Whispering Waltz

• Chittlin’ Cookin’ Time in Cheatham County

• Money Train

• Lonesome Feeling (The Osborne Brothers cover)

• Rosemary

• Far Away Across the Sea (Arthur Smith Trio cover)

• Lighthouse

• Why Haven’t You Loved Me Yet

• Years (John Anderson cover)

• Lesson in Leavin’ (Jo Dee Messina cover)

• American Dreaming

• Dollar Bill Bar (w/ Nikki Lane)

• Fox Hunt

Encore:

• Me and Bobby McGee (Kris Kristofferson cover)

• In Dreams