The Iola Old Car Show recently grew to 4,400-plus spaces, proving that this small Wisconsin town has one of the largest automotive swap meets in the country. Free parking is located adjacent to the show grounds, with shuttle service available to and from the main gates. Well marked routes with signs are easily accessible from highways for spectators. A wide variety of food and refreshments are conveniently available on the show grounds, including complete breakfast, chicken and steak dinners, pizza, hot dogs, hamburgers, brats, barbecue beef, chicken sandwiches, cheese curds, milk shakes, ice cream bars, yogurt, egg rolls, beer and soda.

The Iola Historical Society was organized in 1953 and incorporated in 1956. Since 1979 the original Railroad Depot, built in 1894 and known as “Station 66”, has been the heart of a complex of historical buildings. Other buildings at the Complex include a replicated country schoolhouse and Norwegian immigrant log cabin. All buildings house artifacts from the Iola area. The Iola Historical Society annually sponsors a Strawberry Fest on the second Sunday in August for the public. Besides serving strawberry shortcake for a small donation, special displays are set up in all buildings.

The Iola Winter Sports Club is a non-profit organization that exists to promote the winter sports of cross country skiing and ski jumping, with the focus on family recreation and introducing children to the sports. Each year about 90 children participate in the Youth Ski League which is completely supported by the club through membership fees and grants and donations by area organizations. The IWSC is made up of volunteers who put in many hundreds of hours to provide a good family experience of skiing and hiking.