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Okoboji Events for Every Season

There’s always something happening in Okoboji! From lively summer festivals and family-friendly celebrations to live music, sporting events, and seasonal traditions, the region offers a packed calendar of activities year-round. Browse our Events Calendar to find upcoming happenings, or check out this weekend’s top events to make the most of your visit!

Upcoming Events

Big weekends, live music, local traditions — you never know what you’ll find, but you’ll always be glad you came. Explore the events calendar to join in the fun.

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Dick Bauman Big Band

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Siesta Cruise Public Cruise

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Antique Show & Flea Market – Vick’s Corner

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Flea Market – Treasure Village

sign booth flea market

Grand Champion Antique Show and Blue Ribbon Flea Market

2023FarmersMarket

Farmers Market in the Park

Your Saturday morning routine!  Spend your Saturday mornings at the park with family, friends live music, local vendors, and more! Visit by boat, bike, vehicle or foot!  Enjoy live music, food fresh produce and goods from local vendors, shopping, children’s activities and yoga on the pier every weekend throughout the…
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Mark Your Calendar for Okoboji Fun

Our events calendar is packed with concerts, celebrations, and can’t-miss happenings. See what’s going on when you’re in Okoboji.

Show me events for…

Month When Are You Visiting?
This Weekend May 30 – 31
Next 7 Days May 25 – 31
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Sweet & Savory Small Party Bites Cooking Class – Part 2

May 28
3:00pm - 12:00am
Pearson Lakes Art Center
2201 Hwy 71
Okoboji, IA 51355
Learn More
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Summer Beer Runs

May 28 +3 more
Occurs weekly on Thursday
Starts at 5:30pm
West O Beer
503 Terrace Park Blvd
West Okoboji, IA 51351
Learn More
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Milford Kiwanis Bingo Night

May 28 +1 more
6:00pm - 8:00pm
Spirit Lake VFW
914 Lake St
Spirit Lake, IA 51360
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WPW Headshot1

Wild Prairie Winds: Musical Pairings

May 28
6:00pm - 8:00pm
Little Swan Lake Winery
1350 320th Ave
Estherville, IA
Learn More
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West O Trivia Night

May 28 +3 more
Occurs weekly on Thursday
7:00pm - 9:00pm
West O Beer
503 Terrace Park Blvd
West Okoboji, IA 51351
Learn More
Emerald Hills

Keith Abens Memorial Cyclone Wrestling Club Fundraiser Tournament

May 29
Starts at 8:00am
Emerald Hills Golf Club
808 US Hwy 71 S
Arnolds Park, IA 51331
Learn More
WPW Headshot1

Wild Prairie Winds: Peter and the Wolf

May 29
Starts at 10:00am
Milford Memorial Library
1009 9th St
Milford, IA 51351
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Round Lake Vineyards

Live Music at the Winery: Dave Anderson

May 29 +3 more
Occurs weekly on Friday
Starts at 6:00pm
Round Lake Vineyards & Winery
30124 State Highway 264
Round Lake, MN 56167
Learn More
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Live Music Fridays with Dave Anderson & the Invisible String Band

May 29 +3 more
Occurs weekly on Friday
6:00pm - 8:00pm
Round Lake Vineyard & Winery
30124 MN-264
Round Lake, MN 56167
Learn More
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Barefoot Dock Hop Public Cruise

May 29 +11 more
Occurs weekly on Friday
weekly on Saturday
weekly on Saturday
6:00pm - 9:00pm
The Barefoot Bar
24457 178th St
Okoboji, IA 51355
Learn More
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Ryan Sather

May 29 +2 more
6:00pm - 9:00pm
Block Party Retro Pub
1107 Sanborn Avenue
Okoboji, IA 51355
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Barefoot Bar scaled 3

Live Music by hicktown mafia

May 29 +1 more
7:00pm - 11:00pm
The Barefoot Bar
24457 178th Street
Okoboji, IA 51355
Learn More
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