5 Can't-Miss Things to Do in Downtown DSM This Week: Sept. 18-24

Fall officially arrives this week and Downtown Des Moines (DSM) has a full lineup of ways to welcome the new season. Sip and stroll your way through an evening out, celebrate Oktoberfest traditions or slow down and take in some of the first signs of fall. If you’d rather keep moving, there’s an adults-only night on wheels, while one of comedy’s biggest touring acts is bringing the laughs to Hoyt Sherman Place. Whether you’re planning a date night, gathering a group of friends or simply looking for something different to add to your week, there’s a lot happening in the heart of the city. Here are five can’t-miss things to do in Downtown DSM Friday, Sept. 18 – Thursday, Sept. 24, 2026.

Winefest’s Grand Tasting

Friday, Sept. 18, 2026 | Downtown DSM Historic City Hall
Raise a glass to a night of wine, food and a brand-new setting for one of Winefest’s signature events. The Grand Tasting is moving into Historic City Hall, where you can sample wines from around the world alongside bites from celebrated Central Iowa chefs and restaurants. Wander through the building between tastings and keep an eye out for interactive experiences and surprises along the way. Want to take the evening up a notch? VIP guests start with an exclusive reception on the veranda overlooking the river and Downtown DSM before heading inside for premium wines, food and entertainment. Whether you know your wine or just enjoy drinking it, this 21+ event makes for a memorable Friday night.
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Sip & Stroll Fall Color

Friday, Sept. 18, 2026 | Greater Des Moines Botanical Center
Pour a glass of wine and take a closer look at what’s changing in the garden as summer gives way to fall. Sip & Stroll Fall Color invites you to wander through the Greater Des Moines Botanical Garden with Director of Horticulture Aaron Harpold from 5:30–6:30 p.m. Along the way, you’ll learn what’s blooming now, what’s coming next and what’s happening behind the scenes with the garden’s collection. It’s part garden tour, part happy hour and a relaxing way to spend a Friday evening surrounded by plants. Grab a fellow plant lover, lace up your walking shoes and toast to the changing seasons. This event is for ages 21 and older.
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Just outside Downtown DSM, spend an evening under the stars at SCI’s Star Party: Harvest Moon at Drake Observatory on Friday, Sept. 18, 2026, from 8–10 p.m.

Des Moines Biergarten Oktoberfest

Friday, Sept. 18 – Sunday, Sept. 20, 2026 | Des Moines Biergarten
Dust off the lederhosen and raise a stein because Oktoberfest is taking over Des Moines Biergarten for three days. The free, family-friendly celebration fills the weekend with German and polka bands, stein-holding competitions, sack races, pretzel tosses, yard games and lots of food and bier. Kids can get in on the fun, too, with a Kinder Zone featuring a bounce house, face painting, balloon art and more. Friday kicks things off with the Golden Keg Bicycle Ride and keg tapping, while live music and traditional competitions keep things going Saturday and Sunday. Come hungry, bring the family and get ready to say “Prost!”
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Brenton Night Roll

Saturday, Sept. 19, 2026 | Brenton Skating Plaza
Leave the kids at home and spend Saturday night rolling along the river. Brenton Night Roll turns Brenton Skating Plaza into an adults-only skating spot from 7-10 p.m., complete with music, river views and the Downtown DSM skyline surrounding you. Bring your roller skates or roller blades and cruise around the plaza at your own pace, whether you’re confident on wheels or haven’t skated in years. Admission is just $5, and limited concessions will be available when you need a break. Grab a date or some friends and see Brenton Skating Plaza from a different perspective after dark.
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After rolling through Saturday night, keep moving Sunday, Sept. 20, 2026 at the DSM Open Street Festival, happening just outside Downtown DSM.

John Crist Live!

Sunday, Sept. 20, 2026 | Hoyt Sherman Place
Need a good laugh before the weekend is over? Comedian John Crist is bringing his John Crist Live! Tour to Hoyt Sherman Place this Sunday. Known for his sharp observations, viral sketches and slightly unhinged takes on everyday life, Crist has built an audience of millions online while taking his stand-up across the country. His latest comedy special, “John Crist: Emotional Support”, has racked up millions of YouTube views and he also hosts the “Net Positive with John Crist” podcast. Now you can trade the screen for a seat in the theater and hear his latest material live on a historic stage in Downtown DSM.
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Close out the Gray’s Station Summer Music Series with one final night of live music on Wednesday, Sept. 23, 2026.

Celebrate the change of seasons with free things to do throughout Downtown DSM this week.

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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.