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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!

Wine Class

Dec 4
Starts at 6:00pm
Pearson Lakes Art Center
2201 Hwy 71
Okoboji, IA 51355
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MINGO – Music Bingo

Dec 4 +1 more
Starts at 6:00pm
The Peacock Lounge and Grille
575 Hwy 71
Arnolds Park, IA 51331
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Karaoke at Oak Hill Outdoor

Dec 4 +2 more
Occurs weekly on Thursday
7:00pm—10:00pm
Oak Hill Outdoor
2188 IA-86
Milford, IA 51351
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West O Trivia Night

Dec 4 +2 more
Occurs weekly on Thursday
7:00pm—9:00pm
West O Beer
503 Terrace Park Blvd
West Okoboji, IA 51351
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Holiday Market in the Park

Dec 5
4:00pm—7:00pm
The Roof Garden
244 US-71
Arnolds Park, IA 51331
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Live Music Fridays with Dave Anderson & the Invisible String Band

Dec 5 +1 more
Occurs weekly on Friday
6:00pm—8:00pm
Round Lake Vineyard & Winery
30124 MN-264
Round Lake, MN 56167
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Circus Street Comedy: Mike Young

Dec 5 +1 more
Starts at 8:00pm
Oak Hill Outdoor – 2188
2188 Hwy 86
Milford, IA 51351
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Varsity Rejects

Dec 5 +3 more
Starts at 9:00pm
Captain’s Getaway
107 Broadway St
Arnolds Park, IA 51331
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Holiday Vendor Fair

Dec 6 +1 more
9:00am—3:00pm
Old School Mercantile
10 Broadway St
Arnolds Park, IA 51331
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Holiday Shopping Extravaganza

Dec 6 – Jul 6
9:00am—3:00pm
Parks Marina
24457 178th Street
Okoboji, IA 51355
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Milford Holiday Fantasy Weekend

Dec 6
9:30am—2:00pm
Downtown Milford
Milford, IA 51351
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FREE Community Showing of The Grinch

Dec 6
10:00am—12:00am
Great Lakes Cinema 7
1698 Exchange St
Okoboji, IA 51355
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