May 22, 2026
By: Greater Des Moines Partnership
What’s Happening in DSM This Week: May 22-28
Late May is bringing even more reasons to get out and explore across the Greater Des Moines (DSM) region this week. From family-friendly events and outdoor activities to live entertainment and local traditions, there’s plenty happening if you’re looking to fill your calendar before summer officially kicks into high gear. You can spend time outside with the kids, catch a comedy show, step back in time for a unique experience or wander through a local farmers’ market with coffee in hand.
Whether you’re planning a full weekend of activities or just looking for something easy and fun to add to your week, here are five can’t-miss events happening across DSM May 22-28.
![Touch a Truck]()
Touch A Truck
Friday, May 22, 2026 | Colby Park, Windsor Heights
Touch A Truck is one of those events kids talk about long after it’s over. Hosted by the City of Windsor Heights and the Des Moines Children’s Museum, the event gives families a chance to get up close to big trucks, heavy machinery and all kinds of vehicles you normally only see from a distance. Between climbing inside trucks, honking horns and exploring equipment, there’s plenty to keep little ones entertained for hours. It’s also designed to be welcoming for all families, with noise-cancelling headphones and a calming tent available onsite. Simple, free and guaranteed to burn off some kid energy.
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![Sister Sara]()
Sister Sara Live
Friday, May 22, 2026 | Back Roads Lounge, Johnston
If you’re in the mood for a night filled with singalong-worthy classics, Sister Sara at Back Roads Lounge is bringing plenty of rock energy to kick off the weekend. The longtime Central Iowa cover band leans heavily into crowd favorites from the ’70s, ’80s and ’90s, covering bands like Journey, Def Leppard, Bon Jovi, Tom Petty and more. It’s the kind of setlist where you’ll probably know almost every song by the first chorus. Expect a lively crowd, lots of dancing and a full night of familiar hits that are hard not to sing along to.
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![Jeremiah Watkins]()
Jeremiah Watkins Comedy Show
Friday, May 22 – Saturday, May 23, 2026 | Funny Bone Comedy Club, West Des Moines
If you’re in the mood for a night out that doesn’t take itself too seriously, Jeremiah Watkins at Funny Bone Comedy Club is a pretty easy choice. Known for his quick improvisation, physical comedy and completely unpredictable style, Watkins brings the kind of energy that keeps a crowd locked in from start to finish. Whether you know him from his stand-up specials, podcasts or viral clips online, his live shows are known for feeling spontaneous and interactive in the best way possible. Grab a drink, settle in and prepare to laugh harder than you probably planned to.
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![Historic Baseball at Living History Farms]()
Historic Baseball Demonstration
Saturday, May 23, 2026 | Living History Farmers, Urbandale
Baseball season gets a little old-school at the Historic Baseball Demonstration at Living History Farms. Players dressed in period uniforms will walk visitors through what baseball looked like back in 1876, complete with historic rules, gameplay and a few quirks that definitely wouldn’t fly in modern baseball. (Apparently no cussing or spitting allowed.) It’s part history lesson, part live entertainment and honestly just a really fun way to spend an afternoon. Visitors can even step up for their own turn at bat, which makes the whole thing feel a little more interactive and memorable.
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![Historic Valley Junction Farmers' Market]()
Farmers’ Markets
Various Dates & Locations in DSM
Local farmers’ markets are really hitting their stride this time of year, and DSM has plenty worth checking out. From fresh-picked produce and baked treats to flowers, handmade goods and locally made finds, each market brings its own mix of vendors and community charm. It’s an easy excuse to spend some time outside, wander around with a coffee in hand and enjoy a slower pace for a while.
Whether you stop by your usual market or make a point to try a new one, it’s a great way to shop local and make the most of the season.
There's no shortage of ways to enjoy May around DSM, especially if you're looking for a few free ways to get out, wander around and enjoy the season.
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Greater Des Moines Partnership
The Greater Des Moines Partnership is the largest regional business, economic development and talent development organization in Iowa and the second-largest regional chamber of commerce in the country, serving multiple counties in Greater Des Moines. Together with more than 400 Investors and an Affiliate Chamber of Commerce network of more than 7,200 Regional Chamber Members, The Partnership helps businesses grow and advances quality of life in Greater Des Moines with one voice, one mission and as one region, contributing to a vibrant regional economy.