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.
Holiday Window Lighting
Join us to kick off the Holiday Season in downtown Spirit Lake! Come see the beautiful store fronts lit up for the holiday season, some with live window displays. Santa will arrive around 4:30pm at The Venue on a Fire Truck. Saturday, November 29, 20254:30-6pm
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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.
Live Music Fridays with Dave Anderson & the Invisible String Band
+1 more
Occurs weekly on Friday
6:00pm—8:00pm
Round Lake Vineyard & Winery30124 MN-264
Round Lake, MN 56167
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Circus Street Comedy: Mike Young
+1 more
Starts at 8:00pm
Oak Hill Outdoor – 21882188 Hwy 86
Milford, IA 51351
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Varsity Rejects
+3 more
Starts at 9:00pm
Captain’s Getaway107 Broadway St
Arnolds Park, IA 51331
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Holiday Vendor Fair
+1 more
9:00am—3:00pm
Old School Mercantile10 Broadway St
Arnolds Park, IA 51331
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Holiday Shopping Extravaganza
9:00am—3:00pm
Parks Marina24457 178th Street
Okoboji, IA 51355
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Milford Holiday Fantasy Weekend
9:30am—2:00pm
Downtown MilfordMilford, IA 51351
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Open Clay Studio
+2 more
Occurs weekly on Saturday
10:00am—4:00pm
Pearson Lakes Art Center2201 US-71
Okoboji, IA 51355
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FREE Community Showing of The Grinch
10:00am—12:00am
Great Lakes Cinema 71698 Exchange St
Okoboji, IA 51355
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Escape the Nature Center
4:30pm—7:30pm
Dickinson County Nature Center22785 Nature Center Rd
Okoboji, IA 51355
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The Winery Comedy Tour
6:00pm—7:30pm
Round Lake Vineyards30124 MN-264
Round Lake 56167
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Jazzed Up Christmas
7:00pm—12:00am
The Roof Garden Ballroom91 Lake Street
Arnolds Park, IA 51331
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Christmas at the Winery
12:00pm—3:00pm
Round Lake Vineyards30124 State Hwy 264
Round Lake, MN 56167
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