Win Tickets: Legendary Guitarist Leo Kottke Live at Dubuque’s Five Flags Theater

If you love live music that’s both soulful and a little surprising, mark your calendar now. Acoustic guitar legend Leo Kottke is making his return to Dubuque, taking the stage at the Five Flags Theater on Saturday, December 13th, 2025.

Kottke has spent a lifetime carving out a style that doesn’t really fit into one box. From the moment he first picked up a guitar at age 11, he’s been blending blues, folk, and classical influences into something uniquely his own. His music is at once intricate and approachable, filled with dazzling fingerpicking, unexpected rhythms, and a dry sense of humor that has become just as much a part of his shows as the songs themselves.

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Over the years, Kottke’s career has taken him from small coffeehouses in Minneapolis to international tours, major record deals, and collaborations with big names like Phish bassist Mike Gordon. Along the way, he’s released a long list of albums that showcase his unmatched guitar work, including classics like Mudlark and Greenhouse, as well as more recent projects that prove he’s still pushing boundaries.

Seeing Kottke live is something else entirely. His concerts are a mix of jaw-dropping musicianship and quirky storytelling, with the kind of intimacy that makes you feel like you’re sitting in his living room. It’s the sort of performance that stays with you long after the last note fades.

And here’s the best part: we’re giving you the chance to win tickets to see Leo Kottke at Five Flags Theater. Don’t miss your shot at catching one of America’s true guitar originals in person. Sign up below for your chance to win!

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• Who: Acoustic guitar legend Leo Kottke
• Where: Five Flags Center, Dubuque, Iowa
• When: Saturday, December 13, 2025 – Tickets on sale now