Known for their warm hospitality and rich history, the Heartland states are also home to some of the country’s most celebrated annual events. In addition to music and performances, many events highlight local cuisine, offering visitors a chance to enjoy regional specialties and unique culinary creations.
From thrilling air shows to jazz-filled streets, the Heartland offers unforgettable experiences that celebrate the region’s diverse culture. Whether it’s the roar of jet planes over Chicago, the sounds of jazz echoing through Detroit or the communal pride at a state fair, Heartland festivals provide something for every traveler, making it a destination rich in experiences for groups to explore.
Chicago Air and Water Show
Chicago
One of the most thrilling events on the Chicago summer calendar, the Chicago Air and Water Show has been wowing audiences since 1959. What started as a modest neighborhood event has blossomed into one of the largest and oldest free air and water shows in the United States.
Each year, millions of spectators gather along Chicago’s lakefront to witness breathtaking aerial displays from both military and civilian pilots, including spectacular performances by elite teams like the U.S. Navy Blue Angels and the U.S. Army Golden Knights. Along with these high-flying acts, there are impressive water-based performances, boat-jumping demonstrations and parachuting acts, all set against the stunning backdrop of Lake Michigan.
Spectators typically stake out prime spots along the shoreline, with North Avenue Beach offering an unbeatable view of the aerial action. With roaring engines, daring maneuvers and a festival atmosphere, the two action-packed days aren’t just a feast for aviation fans. Many restaurants and bars host viewing parties, and groups can also hop aboard one of Chicago’s many lakefront boat cruises to enjoy a full buffet, bar service and unobstructed views of the spectacular aerial performances.
Indy 500 Festival
Indianapolis
A staple of Indiana’s culture, the Indy 500 Festival is a month-long celebration leading up to the world-famous Indianapolis 500 race. First held in 1957, the festival now hosts over 50 events, making it one of the most comprehensive prerace celebrations globally. The festival culminates in the grand spectacle of the Indianapolis 500, but there’s much more to enjoy throughout the month. Highlights include the 500 Festival Parade, which showcases elaborate floats, marching bands and race car drivers, and the OneAmerica 500 Festival Mini-Marathon, one of the country’s largest half-marathons.
Groups can expect to immerse themselves in Hoosier culture with events like Breakfast at the Brickyard (where visitors dine on the track and meet racing legends for an unforgettable race-day experience) and the festival’s renowned Kids’ Day.
For groups, there are opportunities to visit the Indianapolis Motor Speedway Museum to see early racing cars, one-of-a-kind vehicles, trophies, drivers’ suits and helmets, and memorabilia from the best names in the sport. The museum also offers exclusive behind-the-scenes access to the historic racecourse. Tour options include the Kiss the Bricks tour, where visitors can take a lap around the famous track and recreate the tradition in which winners of the Indianapolis 500 kiss a remaining section of the original brick-paved racetrack from 1909, and the View from the Top tour, which includes panoramic views from the Pagoda and Victory Podium. For a more intimate experience, the Golf Cart Tour explores restricted areas like Gasoline Alley and the Snake Pit on select days.
Iowa State Fair
Des Moines, Iowa
A state celebrated for its agricultural contributions, Iowa is home to one of the nation’s most iconic fairs — the Iowa State Fair. Since 1854, the fair has been a symbol of Iowa’s deep-rooted connection to farming and rural life. Held every August in Des Moines, it’s one of the largest agricultural and industrial expositions in the world, drawing over a million visitors annually. While the fair’s legendary livestock competitions and award-winning produce are staples, many visitors come for its indulgent food offerings, with 200 stands serving everything from classic corn dogs to more adventurous bacon-wrapped deep-fried treats.
Beyond the agricultural showcases, the fair offers plenty of other activities, including grandstand concerts featuring top national performers, thrilling carnival rides, and lively contests such as pie-eating competitions and talent shows. The Butter Cow, a life-size sculpture carved entirely from butter, remains a fan-favorite attraction.
For visitors seeking more entertainment, the fair also hosts nightly horse shows, tractor pulls, vintage vehicle displays, antique markets, and Fabric and Threads or glass-blowing classes for the more creative minds. Groups can also enjoy the midway filled with games and rides and the Iowa Craft Beer Tent, where regional brews are showcased.
Wichita Riverfest
Wichita, Kansas
Kansas’s largest community event, the Wichita Riverfest, has been a state tradition since 1970.
“Wichita Riverfest is the region’s largest and most anticipated festival,” said Susie Santo, president and CEO of Visit Wichita.
Spanning nine days in late spring or early summer, this event attracts over 400,000 visitors to downtown Wichita, where they can enjoy an eclectic mix of live music, food and family-friendly activities, all centered around the beautiful Arkansas River. The festival kicks off with the iconic Sundown Parade, followed by a packed schedule of concerts, interactive exhibits, river runs and fireworks displays that light up the night sky.
One of the highlights for visitors is the variety of performances at the festival’s multiple stages, where both local talent and national headliners entertain the crowd. Groups can also enjoy art installations, shop at pop-up art markets or participate in the very popular Cardboard Regatta, where teams have 90 minutes to build a river-worthy vessel using cardboard, pool noodles and other basic materials.
“And of course, no visit is complete without sampling the delicious and unique offerings at the downtown food court,” said Santo. “This event is a unique way to experience a summer festival in the heart of the country.”
Groups can also enjoy cruise river tours, try a helicopter ride over the river, rent kayaks and canoes, and attend special events dedicated to the men and women of the U.S. Armed Forces.
Detroit Jazz Festival
Detroit
Labor Day weekend in Detroit wouldn’t be the same without the Detroit Jazz Festival, the largest free jazz festival in the world. Established in 1980, this event celebrates Detroit’s deep jazz heritage and attracts some of the genre’s biggest names, along with thousands of jazz enthusiasts from around the globe. Held across multiple stages in downtown Detroit, the four-day festival offers a diverse lineup of over 60 performances, from contemporary jazz to classic big band and from outdoor amphitheaters to late-night jam sessions at local venues, as well as after-hours concerts at the new Gretchen C. Valade Jazz Center.
In addition to the music, the festival hosts food trucks, workshops, panel discussions, and meet-and-greet opportunities with musicians for a truly interactive experience. Groups can stop by Baker’s Keyboard Lounge, the oldest jazz club in the world; check out art exhibits showcasing jazz-inspired works from local artists; or explore the city’s rich history of jazz and Motown legends through walking tours that guide them to significant locations in Detroit’s music scene.
After the festival, visitors should spend some time exploring the birthplace of the iconic Motown sound with a stop at the Motown Museum. Other local highlights include getting to know Detroit’s rich automotive history and taking in Diego Rivera’s famous Detroit Industry Murals, which capture the spirit of the city’s industrial past.
