Event Category: All Events

  • MML’s Weekend Creator

    MML’s Weekend Creator

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    Join MML for a come-and-go craft time for children and young adults on Saturday, May 30. From 9:30 a.m. to 12:00 p.m., a variety of crafts will be available for you to create. This is a free event.

  • Summer Reading Kick Off Celebration

    Summer Reading Kick Off Celebration

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    The Kick Off Celebration for the 2026 Summer Reading Program will be a movie matinee on Thursday, May 28, at 10:30 a.m. and 1:00 p.m., at the Milford Pioneer Theatre. The movie will be The Land Before Time. If you bring two nonperishable food items, you will receive one free popcorn. Other concession items will…

  • Adam & Jacob

    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!

  • Keifer & Scott

    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.

  • Liveband Karaoke

    Liveband Karaoke

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    Join The Peacock Lounge & Grille for Liveband Karaoke, delicious food, and unique cocktails!

  • Live music at the Winery

    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!

  • The Iron Horse Bar Loop

    The Iron Horse Bar Loop

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    Sportsmans is celebrating 30 years of owning Sportsmans!  Did you know that Sportsmans has been Sportsmans since 1937! This is worth celebrating, and we are celebrating for 3 days straight starting Thursday 4/30/26 and ending with this IRON HORSE BAR LOOP bike ride on Saturday 5/2/26.  The same fun Tiki Ride organizers are also organizing…

  • Shredding Flannel

    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…

  • 90s Kid

    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!

  • Chad Elliott

    Chad Elliott

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    Enjoy live music at Block Party Retro Pub located at Vintage Block Inn & Suites!