On June 28, 2025, the Outlaw Music Festival rolled into Hollywood Casino Amphitheatre in Maryland Heights, Missouri, delivering a vibrant celebration of its 10th anniversary. Headlined by legends Willie Nelson and Bob Dylan, the festival featured a stellar lineup including Nathaniel Rateliff & The Night Sweats, Trampled by Turtles, and Tami Neilson. Despite the summer heat, the event drew a diverse crowd, from longtime fans of Nelson’s outlaw country to younger attendees drawn to the Americana and folk-rock vibes. The laid-back, communal atmosphere was palpable, with the scent of sunscreen and festival fare filling the air.
Set Times and Performances
The show kicked off at 3:00 PM with doors opening, setting the stage for a day of music under the Missouri sun.
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Tami Neilson (4:00 PM – 4:35 PM): New Zealand’s Tami Neilson opened with her soulful blend of country, rockabilly, and blues. Her powerful vocals and retro swagger set a high-energy tone, warming up the sparse early crowd with tracks like “Big Boss Mama.” Her 35-minute set was a perfect appetizer, though some fans noted her placement might have deserved a later slot for a larger audience.
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Trampled by Turtles (4:55 PM – 5:55 PM): The Duluth bluegrass outfit brought their frenetic energy, tearing through a set of high-octane string-band tunes. Songs like “Wait So Long” had the crowd on their feet, with their tight harmonies and breakneck banjo riffs cutting through the humid air. Their performance earned high praise, with some attendees calling it a highlight for its raw, infectious vibe.
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Nathaniel Rateliff & The Night Sweats (6:25 PM – 7:40 PM): Rateliff and his band delivered a soul-rock masterclass, blending gritty vocals with horn-driven grooves. Hits like “S.O.B.” and “I Need Never Get Old” ignited the amphitheater, with the crowd singing along fervently. Their 75-minute set was a standout, radiating energy and heart, though a few fans wished for a longer performance given their momentum.
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Bob Dylan (8:10 PM – 9:25 PM): Dylan, ever the enigmatic troubadour, took the stage with a set heavy on his later works, interspersed with classics like “All Along the Watchtower.” His gravelly voice and minimalist stage presence polarized the crowd—some revered the raw authenticity, while others found it less engaging compared to the high-energy acts before him. At 84, Dylan’s performance was a testament to his enduring legacy, though it leaned more introspective than crowd-pleasing.
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Willie Nelson & Family (9:55 PM – 10:55 PM): Closing the night, Willie Nelson, at 92, proved why he’s the heart of the Outlaw Music Festival. Backed by his Family band, he delivered a heartfelt set including “On the Road Again,” “Always on My Mind,” and “Whiskey River.” His voice, warm and weathered, carried the weight of decades, and his understated guitar work on Trigger was flawless. The crowd’s adoration was electric, though some noted the set felt short at just an hour. Nelson’s charisma and the communal sing-alongs made it a fitting capstone.
The 2025 Outlaw Music Festival at Hollywood Casino Amphitheatre was a testament to Willie Nelson’s enduring vision of uniting genre-defying artists in a celebration of music’s rebellious spirit. With a crowd spanning generations, the event captured the essence of Americana—raw, soulful, and unapologetic. While Dylan’s set may not have resonated with all, the collective energy of the lineup and Nelson’s timeless performance made it a memorable night. For fans of country, folk, and rock, this festival remains a must-see.
