October 09, 2026
By: Greater Des Moines Partnership
Your Guide to Things to Do in Greater DSM This Week: Oct. 9-15
October was made for getting out and exploring Greater Des Moines (DSM), and there’s something happening in nearly every direction across the region this week. Celebrate one of the DSM’s longest-running fall traditions, hunt for vintage treasures or spend a Sunday moving from porch to porch with live music as your soundtrack. You can also put on a Halloween costume and hit the dance floor or spend a day learning more about the Indigenous cultures that have shaped Iowa for centuries. From Winterset and West Des Moines to Urbandale, Adel and Cumming, there’s a different kind of experience waiting in each community. Here are five can’t-miss things to do across DSM this week.
![Heartland Halloween Swing Dance]()
Halloween Swing Dance with Live Music
Friday, Oct. 9, 2026 | Valley Junction Activity Center, West Des Moines
Grab your dancing shoes and your Halloween costume for a Friday night of swing dancing and live jazz in Valley Junction. Heartland Swing kicks things off with a beginner Lindy Hop lesson from 7:15-8 p.m., so don’t worry if you’ve never tried it before. No partner or experience is needed, and the lesson is included with admission. Then Junction Jazz Society takes over from 8-10:30 p.m. while dancers fill the floor. Costumes are encouraged but not required, so go all out or simply show up ready to dance. Admission is $15 per person, with cash or Venmo accepted at the door.
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![Indigenous Iowans Day]()
Indigenous Iowans Day
Saturday Oct. 10, 2026 | Living History Farms, Urbandale
Spend Saturday learning more about the Indigenous Peoples who have shaped Iowa’s story during Indigenous Iowans Day at Living History Farms. Visit the 1700 Ioway Farm and dig deeper into how the Ioway lived on the land that would eventually become Iowa, while also learning about other Indigenous Peoples who have called and continue to call this land home. Demonstrations, games, crafts and special activities throughout the day offer different ways to explore these histories and cultures. The event runs from 9 a.m.–4 p.m., and all Indigenous Iowans Day activities are included with general admission to Living History Farms.
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![Vintage & Made Fair]()
Vintage & Made Fair
Saturday, Oct. 10, 2026 | Dallas County Fairgrounds, Adel
If vintage finds and handmade goods are your weakness, clear some room in the car before heading to Adel. Vintage & Made Fair brings more than 150 vendors to the Dallas County Fairgrounds for one big day of shopping. Browse antique and vintage home décor, jewelry, handcrafted goods, outdoor accents, seasonal flora and all kinds of one-of-a-kind finds while enjoying food trucks and live music along the way. Whether you arrive hunting for something specific or just want to see what catches your eye, give yourself time to wander. The fair runs from 9 a.m.–3 p.m. Admission is $10 and children ages 12 and younger get in free.
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![Madison County Covered Bridge Festival]()
Madison County Covered Bridge Festival
Saturday, Oct. 10 – Sunday, Oct. 11, 2026 | Courthouse Square, Winterset
Fall in Madison County wouldn’t be complete without the Covered Bridge Festival. A tradition since 1970, the annual celebration takes over the Winterset courthouse square with more than 140 food, arts and crafts vendors, continuous live music, children’s activities and more throughout the weekend. Wander the square, grab something good to eat and make some time to explore the famous covered bridges that give the festival its name. The fun runs from 9 a.m.–7 p.m. Saturday and 9 a.m.–3 p.m. Sunday, with the parade kicking off at 3 p.m. Admission is just $3 at the gate and children ages 11 and younger get in free.
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![Middlebrook Porchfest]()
Middlebrook Porchfest
Sunday, Oct. 11, 2026 | Middlebrook Farm, Cumming
Grab a lawn chair and spend your Sunday following the music through the Great Western Crossing neighborhood in Cumming during the first-ever Middlebrook Porchfest. Starting at 11 a.m., musicians take over neighborhood porches one by one, with Randy Burk and the Prisoners, Heath Alan, Bonne Finken, Other Brothers and The Soul Searchers each getting their turn. When the neighborhood portion wraps up, follow the crowd to The Farmhouse porch on Middlebrook Farm for a longer performance from Brother Trucker at 4 p.m., along with food trucks, wine and beer. It’s a laid-back way to spend a fall Sunday, discover some music and experience Middlebrook from porch to porch.
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For another Cumming outing later in the week, grab a drink and get creative during a Paint & Sip at Middlebrook Mercantile on Tuesday, Oct. 13, 2026.
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