Sherman Wayside Park was one of a few remaining waysides that once dotted Route 66 from Chicago to California, offering weary travelers in Depression-era cars without air conditioning a place to stop for a picnic and rest on their journey west. Route 4, the first paved road between Chicago and St. Louis, became part of Route 66 in 1926, and from 1936 to 1961 the highway followed a four-lane bypass route. Many local residents also picnicked at Sherman Wayside Park and visited with travelers from around the world. Flooding on the Sangamon River near Sherman frequently closed Route 66, and the road later became a relic of the past when I-55 bypassed Springfield and Sherman.
