Memorial Day Weekend marks the unofficial start of summer in Okoboji, and there’s no better place to kick off lake season than right here in the Iowa Great Lakes. From live music and lake cruises to family-friendly activities and community events, the holiday weekend is packed with ways to enjoy everything Okoboji has to offer.
Whether you’re spending the weekend on the water, exploring local shops, enjoying outdoor dining, or taking in live entertainment, Memorial Day Weekend in Okoboji brings together the energy and excitement that make summers at the lake so special.
Friday, May 22
The holiday festivities begin Friday with a full lineup of entertainment, live music, and lakeside fun throughout the area.
Live Music & Entertainment
- LIVE MUSIC: Two Ol’ Fishheads at Next Level Rooftop at Captain’s Getaway at 4:00pm
- Siesta Cruise Public Cruise — Boat cruise departing from Barefoot Bar from 5:00pm–6:15pm
- LIVE MUSIC: Sounds Fishy at Mullets from 5:00pm–9:00pm
- LIVE MUSIC: Ryan Sather at Block Party Retro Pub from 6:00pm–9:00pm
- LIVE MUSIC: Dave Anderson at Round Lake Vineyards & Winery from 6:00pm–8:00pm
- Barefoot Dock Hop Public Cruise — Boat cruise departing from Barefoot Bar from 6:00pm–9:00pm
- LIVE MUSIC: Hicktown Mafia at Okoboji Barn Bar & Grill at 7:00pm
- LIVE MUSIC: Cam Cummings at Barefoot Bar from 7:00pm–11:00pm
- Karoake with Jason Grinnen at Snappers at 8:00pm
- LIVE MUSIC: Sushi Roll at the Okoboji Store at 8:00pm
- LIVE MUSIC: Skitzo Fonik at Captain’s Getaway at 9:00pm
- LIVE MUSIC: The Fishheads at Mullets from 9:00pm–1:00am
- LIVE MUSIC: Jeremy DeWall at Nautical Okoboji from 10:00pm–2:00am
Saturday, May 23
Saturday brings even more opportunities to experience the best of Okoboji. From community events and farmers markets to live music and lake activities, there’s something happening around every corner.
Community Events & Activities
- ALL DAY: Memorial Day Veterans Free Greens Fees at Brooks Golf
- Farmers Market in the Park on Lake Street in Arnolds Park from 8:30am–12:30pm
- Memorial Day Flea Market at Treasure Village from 9:00am–5:00pm
- Memorial Day Flea Market at Vick’s Corner from 9:00am–5:00pm
- Antique Show & Flea Market at Dickinson County Expo from 9:00am–5:00pm
- Shake the Lake Public Cruise — Boat cruise departing from Barefoot Bar from 1:00pm–4:00pm
- Sunset Cruise Public Cruise — Boat cruise departing from Barefoot Bar from 8:00pm–10:30pm
Live Music Around the Lakes
- LIVE MUSIC: Boon & Lambert at Farmers Market in the Park from 8:30am–12:30pm
- LIVE MUSIC: Aventi at Mullets from 1:00pm–5:00pm
- LIVE MUSIC: Keifer & Scott at the Okoboji Store at 1:00pm
- LIVE MUSIC: Live Music at the Round Lake Vineyards & Winery from 2:00pm–6:00pm
- LIVE MUSIC: Davy Williamson at Barefoot Bar from 2:30pm–6:30pm
- LIVE MUSIC: Two Ol’ Fishheads at Next Level Rooftop at Captain’s Getaway at 4:00pm
- LIVE MUSIC: Sounds Fishy at Mullets from 5:00pm–9:00pm
- LIVE MUSIC: Tim Horsman at Block Party Retro Pub from 6:00pm–9:00pm
- LIVE MUSIC: Cam Cummings at Barefoot Bar from 7:00pm–11:00pm
- LIVE MUSIC: Schoon Brothers at the Peacock Lounge at 7:30pm
- LIVE MUSIC: Sushi Roll at the Okoboji Store at 8:00pm
- LIVE MUSIC: Skitzo Fonik at Captain’s Getaway at 9:00pm
- LIVE MUSIC: The Fishheads at Mullets from 9:oopm–1:00am
- LIVE MUSIC: DJ Wheelz at Portside from 10:00pm–2:00am
Sunday, May 24
Sunday in Okoboji offers another full day of lake fun, entertainment, and opportunities to relax with friends and family before the holiday weekend comes to a close. Whether you’re enjoying brunch by the water, heading out on the lake, or catching another round of live music, the atmosphere throughout the Iowa Great Lakes is hard to beat.
Community Events & Activities
- ALL DAY: Memorial Day Veterans Free Greens Fees at Brooks Golf
- Dad’s Belgian Waffles Fundraiser at Okoboji Summer Theatre from 8:30am–12:30pm
- Memorial Day Flea Market at Treasure Village from 9:00am–5:00pm
- Memorial Day Flea Market at Vick’s Corner from 9:00am–5:00pm
- Antique Show & Flea Market at Dickinson County Expo from 9:00am–5:00pm
Live Music Around the Lakes
- LIVE MUSIC: Aventi at Mullets from 1:00pm–5:00pm
- LIVE MUSIC: Keifer & Scott at the Okoboji Store at 1:00pm
- LIVE MUSIC: Davy Williamson at Barefoot Bar at 2:30pm
- LIVE MUSIC: Two Ol’ Fishheads at Next Level Rooftop at Captain’s Getaway at 4:00pm
- LIVE MUSIC: Anthony Koester at the Peacock Lounge at 5:00pm
- LIVE MUSIC: Dude Where’s My Keys at Mullets from 5:00pm–9:00pm
- LIVE MUSIC: Tanner Frisbee at Block Party Retro Pub from 6:00pm–9:00pm
- LIVE MUSIC: Cam Cummings at Barefoot Bar from 7:00pm–11:00pm
- LIVE MUSIC: Sushi Roll at the Okoboji Store at 8:00pm
- LIVE MUSIC: Skitzo Fonik at Captain’s Getaway at 9:00pm
- LIVE MUSIC: The Fishheads at Mullets from 9:00pm–1:00am
- LIVE MUSIC: Gar Lambert at Nautical Okoboji from 10:00pm–2:00am
Monday, May 25
Memorial Day Monday wraps up the holiday weekend with community events, live music, and time spent honoring those who have served our country. While many visitors begin heading home, the lakes area still offers plenty of ways to enjoy one final day of summer kickoff celebrations.
Community Events & Activities
- ALL DAY: Memorial Day Veterans Free Greens Fees at Brooks Golf
- Monday Funday 4-Person Best Shot Tournament at Emerald Hills Golf Club at 8:00am
- Memorial Day Flea Market at Treasure Village from 9:00am–5:00pm
- Memorial Day Flea Market at Vick’s Corner from 9:00am–5:00pm
- Antique Show & Flea Market at Dickinson County Expo from 9:00am–3:00pm
- Memorial Day Remembrance Ceremony at Florence Park in Milford at 11:00am
Live Music & Entertainment
- LIVE MUSIC: Keifer & Scott at the Okoboji Store at 1:00pm
- LIVE MUSIC: Itty Bitty Boji Band at Barefoot Bar from 2:00pm–6:00pm
- LIVE MUSIC: Ryan Sather at Next Level Rooftop at Captain’s Getaway at 4:00pm
- LIVE MUSIC: Sounds Fishy at Mullets from 5:00pm–9:00pm
- LIVE MUSIC: Dick Bauman Big Band at Pearson Lakes Art Center from 7:00pm–9:00pm
Before the long weekend comes to an end, many families and visitors take advantage of one last boat ride, patio dinner, or lakeside walk. Memorial Day Weekend in Okoboji is more than just the start of summer — it’s a tradition filled with community, connection, and unforgettable memories at the lake. The team at Okoboji Realty are all local, feel free contact us if you have any questions about any local events and activities!
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