25 Top Midwest Events in September | Midwest Living

25 Top Midwest Events in September

A pumpkin festival, a vintage bus rally and the National Flat Pick Championships are just some of the top Midwest events in September.


Morton Pumpkin Festival, Morton September 13–16 Your pumpkin spice latte-loving friends will be orange with envy when you post photos of carving contests, the pumpkin parade and delicacies like pumpkin chili and pancakes (mortonpumpkinfestival.org). 

Chicago Architecture Biennial, Chicago September 16–January 7, 2018 This free event celebrates architecture through activities, events and exhibitions. Several sites are joining in, including the DePaul Art Museum (chicagoarchitecturebiennial.org). 

Galena Oktoberfest, Galena September 30 Head to Depot Park to discover a taste of Deutschland through polka lessons, wiener dog races and beer (galenalions.org). 


Vintage Bus Rally, Evansville September 22–24 At the newly refurbished Greyhound Station, view tricked-out buses of all makes and models (from 1914 to 1992). Then take a ride in some of the buses (busboyscollection.org). 

Block Bash, French Lick September 15–17 It takes a keen eye and a chain saw to turn giant wood blocks into works of art. See carvers compete, then purchase ready-made wooden wares at the auction and artist marketplace (bearhollowwoodcarvers.com). 

Block Bash

Block Bash


An Evening with Ira Glass, Des Moines September 16 The host and producer of NPR’s This American Life takes the stage at Hoyt Sherman Place. Expect musings and insights into his storytelling process (hoytsherman.org). 


Irving Penn: Beyond Beauty, Wichita September 30–February 4, 2018 The late photographer is known for images that graced the pages of Vogue. See 146 of his shots at the Wichita Art Museum (wichitaartmuseum.org). 

Walnut Valley Festival, Winfield September 13-17 Strings sing at this festival in its 46th year, featuring the National Flat Pick Championships. At the Winfield Fairgrounds, watch acoustic aficionados compete in fiddle, mandolin and banjo contests (wvfest.com).  

Walnut Valley Festival

Walnut Valley Festival


Art and Apples Festival, Rochester September 8–10 Nearly 300 artists from across the country will fill Rochester Municipal Park. Try a tasty apple treat while you mull over your next fine-art purchase (pccart.org/festival). 

Wine and Harvest Festival, Paw Paw September 8–10 Michigan wines flow freely at this viticultural jubilee, which also includes local beers. Participating locations are spread throughout downtown Paw Paw (wineandharvestfestival.com). 

Bay Harbor Home Tour, Bay Harbor September 16 Take a two-hour trolley tour of Lake Michigan shore homes with towering turrets and Victorian-inspired designs (bayharborfoundation.org). 


Duluth Hot Air Balloon Festival, DulutSeptember 15–17 At Bayfront Park, watch hot air balloons take to the late-summer skies, or try a tethered ride (kernkompany.com). 

Marigold Days, Mantorville September 9–10 Marigolds shine brightly at this classic festival featuring a sizable flea market, a parade, eats from around the region and a quilt show. Running for 52 years, it’s a charming local favorite (marigolddays.com). 


Strange Folk Festival, St. Louis September 22–24 If it’s hip, handmade and adorable, you’ll find it at this festival staged at Lafayette Park. Finds might include finger puppets, quirky greeting cards and zombie-theme kitchen accessories (strangefolkfestival.com). 


Omaha Restaurant Week, Omaha September 15–24 Yes, Omaha is renowned for its beef, but that’s not all you’ll find during the city’s annual restaurant week. Feast on unique culinary creations from local dining spots offering prix fixe meals (visitomaha.com). 

Lincoln Calling, Lincoln September 28–30 Artistic expression colors this multilayered music event held at indoor and outdoor venues. Musical acts like Charli XCX are scheduled, along with art displays, a night market and hands-on workshops (lincolncalling.com). 

North Dakota

Downtown Street Fair, Grand Forks September 8–9 Grand Forks will turn over downtown to thousands of visitors for handmade wares and local bites (grandforks.org). 

Dakota Nights Astronomy Festival, Medora September 15–17 Astronomy won’t seem so lofty at this down-to-earth festival at Theodore Roosevelt National Park. Stargaze beside astronomers and historians, launch rockets and attend presentations (nps.gov/thro).


Ohio River Sternwheel Festival, Marietta September 8–10 Powerboats take the back seat as old-time riverboats glide back into the spotlight on the Ohio River. The festival includes music on the entertainment barge and fireworks shot from vessels on the river with choreographed music (ohioriversternwheelfestival.org). 

Tour de Donut, Troy September 16 Doughnuts become sugary badges of honor at this bike-and-eat race. Shave five minutes off your time for each stop where you devour a doughnut. But that only helps if you can pedal the rest of the course with distance options of 16, 32 or 64 miles (thetourdedonut.com). 

Columbus Coffee Fest, Columbus September 30–October 1 Join kindred caffeine-cravers as local roasters take up residence in historical buildings at Ohio Village. They’ll serve up dizzying drink options—even coffee-flavored cocktails and beers—for you to sample, and then  you can buy coffee to take home (columbuscoffeefest.com). 

South Dakota

Grape Stomp Celebration, Roshot September 9–10 With the Wind Vineyard and Winery invites you to feel grapey ooze between your toes. (Pro tip: Don’t wear white.) The gathering includes scheduled competitions and wine tastings, so you can also kick back and enjoy the fruits of others’ labor (withthewindwinery.com). 

North Country Fiber Fair, Watertown September 22–24 If you want to knit that sweater before winter, gather inspiration at the Codington County Extension Complex. Purchase homespun yarn from vendors, and watch herding and shearing (northcountryfiberfair.org). 


Taste of Lake Geneva, Lake Geneva September 9 Treat your taste buds to an afternoon of Lake Geneva’s tastiest fare as you stroll the lakefront at Flatiron Park. Try bites from a spread of local restaurants and wash it down with a pint or a glass of wine (lakegenevadowntown.com). 

Maker Faire, Milwaukee September 23–24 Gizmos and gadgetry abound at this techie gathering presented at Wisconsin State Fair Park by the Betty Brinn Children’s Museum. Marvel at robotics and science demos and see the impact of ingeniuty (makerfaire.com). 


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