My wife and I attended the annual Kirchenfest last August, and we plan to go every year from here on out. This event (translated Church Festival) is sponsored by St. Paul Catholic Church, and it celebrates the wonderful combination of church and German heritage that exists in the community.
The city usually blocks off about six city blocks surrounding the church for this festival, at which the attendance usually exceeds 15,000 people. This really is amazing when one realizes that the city only has about 8600 residents. There are games, food, and entertainment in abundance. My wife was amazed to realize that the building blocks of community life in this area revolve around the five "B's": Beer, Brats, Bingo, Baseball (St. Louis Cardinals), and Bowling. If you really want a flavor of the Midwest, you will see the first three of these incorporated into the Kirchenfest. The other two are close at hand, also.
Events at the Kirchenfest begin about 10am and run until almost midnight on both Saturday and Sunday. They include 2k and 5k runs, cheerleading exhibitions from local schools, live polka, rock and roll, jazz, and blues music featuring nationally prominent local groups, an auction of unique items, including sports memorabilia, an eight foot-wide pizza, weekend vacation getaway trips, dinner parties, professional sporting event tickets, meals at local restaurants, steaks, and many antiques, and a traditional bavarian meal.
As you visit the Midwest in the autumn, I highly recommend that you stop in on this annual event in Highland. There is no other event of this nature in the United States.