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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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West O Trivia Night

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Mediterranean Dinner Series

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Trunk or Treat | Hosted by GrapeTree

Oct 30
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Keelson Harbour Halloween Trick ‘r Treat & Carnival

Oct 30
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Modern Granny Square with Sandie Smith

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WOW: Women’s Okoboji Weekend

Nov 7 – Nov 8
Enjoy fashion, food, fun and thousands of dollars in prizes at WOW- Women’s Okoboji Weekend, November 7-8 at the Dickinson County Expo Building.
LEARN MORE

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.

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Trunk or Treat | Hosted by GrapeTree

Oct 30
4:30pm—6:00pm
GrapeTree Medical Staffing, LLC
2501 Boji Bend Drive Suite 100
Milford, IA 51351
Learn More
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Keelson Harbour Halloween Trick ‘r Treat & Carnival

Oct 30
4:30pm—6:00pm
Keelson Harbour
2810 Aurora Ave
Spirit Lake, IA 51360
Learn More
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Mediterranean Dinner Series

Oct 30
Starts at 6:00pm
Pearson Lakes Art Center
2201 Highway 71 N
Okoboji, IA 51355
Learn More
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Modern Granny Square with Sandie Smith

Oct 30
Starts at 6:00pm
Pearson Lakes Art Center
2201 Hwy 71 N
Okoboji, IA 51355
Learn More
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West O Trivia Night

Oct 30 +7 more
Occurs weekly on Thursday
7:00pm—9:00pm
West O Beer
503 Terrace Park Blvd
West Okoboji, IA 51351
Learn More
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Trick or Treat with Milford Businesses

Oct 31
3:30pm—5:00pm
Downtown Milford
Milford, IA 51351
Learn More
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Trick Or Treat at Accura HealthCare & Stonebridge Suites of Milford

Oct 31
3:30pm—5:00pm
Accura Healthcare of Milford
1600 13th St
Milford, IA 51351
Learn More
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Live Music Fridays with Dave Anderson & the Invisible String Band

Oct 31 +6 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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Masquerade Party

Oct 31
7:00pm—11:00pm
Snappers Turtle Bay Cafe
24457 178th Street
Okoboji, IA 51355
Learn More
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Halloween Costume Contest and Karaoke

Oct 31
7:00pm—12:00am
Sportsmans
1605 Hill Ave
Spirit Lake, IA 51360
Learn More
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Shirts and Skins

Oct 31 +3 more
Starts at 9:00pm
Captain’s Getaway
107 Broadway St
Arnolds Park, IA 51331
Learn More
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Fall Vendor Show

Nov 1
9:00am—3:00pm
The Shops at Old School Mercantile
10 W Broadway St
Arnolds Park, IA 51331
Learn More
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