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  • Jud Hailey Trio

    Join us for a great night of live music during Winter Games with crowd favorite Bud Hailey!

  • Holiday in the Ville

    Holiday in the Ville : A Festive Celebration!  Join us for a magical evening in Downtown Estherville as we celebrate the long-standing tradition of the Chocolate Walk from 4-7 PM. Stroll through our charming streets while sampling delightful sweet treats that will kick off your holiday shopping with a sprinkle of cheer! Enjoy free horse-drawn…

  • Circus Street Comedy: Free Comedy with Jessimae Peluso

    Circus Street Presents: Free comedy with Jessimae Peluso on Sunday, November 16th. Live music from loakal favorite, Boon & Lambert before and after the show! For nearly two decades, Jessimae Peluso has been captivating audiences around the world with comedy that’s as fearless as it is healing. Known for her breakout role on MTV’s Girl…

  • Circus Street Comedy: Lucas Hirl

    He’s an Iowa boy who made a name from himself as a Comedy Store regular. I shot his special last year in Des Moines called DARK FARMER. You all are in for a treat!!! He’s done some big things below: Lucas Hirl is an LA-based comedian from the heartland of Iowa, known for his dry, dark-farmer…

  • Circus Street Comedy: Mike Young

    CIRCUS STREET COMEDY BY MIKE YOUNG• Live in Okoboji for TWO nights!• Detroit native Mike Young is an original voice in comedy. After touring with Dave Chapelle, Joe Rogan, Sebastian Maniscalco & Bob Saget, Young headlines nationwide with his down-to-earth stand up.• Mike wrote and directed several feature films, using his comedy voice for the…

  • Iowa Ice Show

    6th Annual Iowa Ice Show at The Hook Up, Oak Hill Outdoor – 2188!SATURDAY, NOVEMBER 29, 2025 – ALL DAY! • See the latest ice fishing products from top manufacturers! • Vendor reps, staff, guides, and ice fishing experts demo & are available to answer your questions! Stay tuned for special guest announcement! – visit with…

  • Holiday Vendor Fair

    Holiday Vendor Show at the Old School Mercantile. Saturday and Sunday December 6/7 from 9AM-3PM, Visit from Santa, donations for Humane Society, shopping, and more! Mark your calendars and watch our page for vendor sign up link.

  • Christmas Grand Lighting

    Join us for the grand lighting of our Christmas light display for the 2025 season. Cost: only $5 per car! This just helps to cover some of the extra cost of lights & extra staff for grand lighting night.  There will be free hot cocoa, cotton candy & popcorn. Plus a food truck (to be…

  • Wine Pairing Dinner

    Enjoy a 5 course wine pairing dinner! Explore how the flavors of food evolve as we introduce each new course. Doors Open – 6:00 PM 1st Course served at 6:30 PM Cash Bar Available Advanced Purchase is required. Menu is TBD. Cost: $75 per person

  • Wine Pairing Dinner

    Enjoy a 5 course wine pairing dinner! Explore how the flavors of food evolve as we introduce each new course. Doors Open – 5:00 PM 1st Course served at 5:30 PM Cash Bar Available Advanced Purchase is required. Menu is TBD. Cost: $75 per person