Event Category: Live Music & Nightlife
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Adam & Jacob
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Adam & Jacob are 2 musicians who bring a high energy show, a few lame jokes, and sometimes a banjo!
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Keifer & Scott
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Keifer and Scott deliver a set packed with familiar favorites, rich harmonies, and laid-back energy that’s perfect for a night out in Okoboji. Join them at the Okoboji Store for great music, good drinks, and an easygoing vibe.
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The peacock 1-Year Anniversary Celebration
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Join The Peacock Lounge & Grille to celebrate t heir 1 year anniversary celebration! Enjoy $1 off drinks all day! Come early for dinner & stay for live music by Decoy from 8-11pm.
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Live music at the Winery
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Enjoy live music at Round Lake Winery. With a full summer line up and a variety of seasonal events and wines to enjoy, add this to your summer bucket list!
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Shredding Flannel
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Join us for another night of live music at Captains Getaway with Shredding Flannel! Hold on to your doc Martens and brace yourself for a wild sonic journey back to the era when flannel shirts were as ubiquitous as dial-up internet! Introducing shredding flannel, the hottest 90s cover band to hit the midwest like a…
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90s Kid
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Join us for a fun night of live music at Captain’s Getaway with 90s Kid! Come enjoy the best of the 90s!
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Lakeside Jukebox
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Enjoy live music at Block Party Retro Pub located at Vintage Block Inn & Suites!
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Wild Prairie Winds: Peter and the Wolf
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We are excited to be returning for our third annual Iowa Great Lakes Summer Chamber Music Festival from May 26-29, 2026. The festival’s mission is to provide accessible classical music experiences to the Iowa Great Lakes region. Our third year of this festival includes performances at the Lakeside Laboratory, Little Swan Lake Winery, and Milford Memorial Library. …