Your Weekly Downtown DSM Plan: Jan. 23-29 Events

January might be winding down, but Downtown Des Moines (DSM) is heating up with a fresh lineup of events to keep the winter blues at bay. This week brings a fun mix of live music, indoor markets and flavorful experiences — from wine and chocolate pairings to throwback tribute shows. Whether you’re a longtime cycling fan, a local shopping enthusiast or just looking for an excuse to get out of the house, there’s something happening to match your vibe. You can browse one-of-a-kind goods, catch a rock concert, toast to local flavors or start planning your next biking adventure. Scroll on for five can’t-miss things to do in Downtown DSM from Jan. 23-29.

Big Head Todd & the Monsters

Friday, Jan. 23, 2026 | Hoyt Sherman Place
Longtime fans and new listeners alike will want to grab tickets to see Big Head Todd & the Monsters light up Hoyt Sherman Place. With four decades of experience and a platinum record under their belt, this Colorado-based rock band brings a soulful, bluesy edge to every performance. Expect a setlist filled with sing-along classics and electric energy. If you’re craving a live show that hits all the right nostalgic notes without missing a beat, this one is a must. Turn it up, sing it loud and let the music move you.
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Splurge

Friday, Jan. 23 - Saturday, Jan. 24, 2026 | West End Salvage
Wine, cheese, chocolate and vibes. Head to West End Salvage for one of the most delicious events of the season: Splurge! This two-night party features tasty sips and bites, live music and a truly unforgettable venue filled with vintage charm. It’s a cozy, classy night out where you can treat yourself to the good stuff. Tickets are $75 online ($85 at the door) and worth every bite. Whether you’re going with a date or your favorite group of friends, this is the kind of January night you’ll be talking about for months.
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Elton & Billy: A Tribute to Billy Joel & Elton John

Saturday, Jan. 24, 2026 | Wooly’s
Rocket Man meets Piano Man in this epic dual tribute show at Wooly’s. “Elton & Billy – The Tribute” is a full-sensory concert experience that brings the sounds, swagger and sparkle of two musical legends to the stage. Expect outrageous outfits, your favorite lyrics and a live band backing spot-on performances by Andy Anderson (as Elton) and Tony Bohnenkamp (as Billy). From “Tiny Dancer” to “Scenes from an Italian Restaurant,” it’s three hours of back-to-back iconic hits and big nostalgia. Grab your friends and relive the magic!
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WinterFest Market

Saturday, Jan. 24, 2026 | EMC Expo Center
Feeling the winter slump? The WinterFest Market at the EMC Expo Center is the perfect pick-me-up. Shop one-of-a-kind goods from local makers, sip something warm and take in the cozy vibes. From handmade candles and jewelry to sweet treats and seasonal finds, there’s something for every kind of shopper. Plus, it’s all indoors — no coat required. Support small businesses, find a post-holiday treasure (or early Valentine’s Day gift!) and enjoy the kind of community cheer that warms you from the inside out.
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Iowa Bike Expo

Saturday, Jan. 24, 2026 | Iowa Events Center
Cyclists, this one’s for you! The Iowa Bike Expo rolls into the Iowa Events Center on Saturday with hundreds of vendors, the latest gear and major inspiration for your next ride. Admission is free, and it’s a great chance to connect with fellow biking enthusiasts, discover new routes and maybe plan a 2026 cycling bucket list. After the expo, stick around for the Bike Banquet, featuring food, drinks, live music and keynote speakers like pro cyclist Ayesha McGowan and Olympian Connor Fields. It’s the perfect way to toast the biking community and support safe, fun cycling in Iowa.
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January is serving up fresh energy in Downtown DSM, with plenty of free ways to get out and explore.

For this week’s events and more, find tips on Downtown Des Moines (DSM) parking and navigation. For additional events and seasonal festivities coming up in Downtown DSM, visit the events calendar. Plus, follow @downtownDSMUSA on Instagram for even more things-you-just-can’t-miss happening around Downtown.