The story of human habitation in the Little Sioux River Valley began thousands of years ago. Archaeologist have established the existence of the Mill Creek Indian culture north of Cherokee in 1200 A.D. In the time of the early French traders, the river was important in the fur trade and was a route of the Plains Indians to the pipestone quarries in Minnesota.
The area’s geological history is just as fascinating. The three glacial advances of the western limit of the Wisconsin glacial period are marked at different points in the valley. A watchful eye may discover clues of the area’s glacial past as several fossils, agates and other interesting rocks can be found along the sandbars within the river. The Little Sioux River winds through Cherokee County, making it one of the most scenic in western Iowa. The river and its tributaries have carved deep into the glacial till. Many high points afford a beautiful view, best of all is seen from the top of Pilot Rock, a large boulder of red Sioux quartzite left by the last glaciations. On a hill south of Cherokee, the rock served as a guidepost and meeting place for Indians and white explorers and has given the Little Sioux the name of “Woven Rock River.”
Cherokee County was one of the 49 divided from Indian Treaty lands by the Third Iowa Assembly in 1851. The lawmen picked names that had no connection with the area or with its history.
Pioneers made their homes in the fertile, wooded valley before venturing to develop the open plains. After scouting the area in 1856, Robert Perry picked a spot by the river in Pilot township for the county’s first home. While getting supplies at Sergeant Bluff, he met two scouts of the Milford, Massachusetts Emigration Company. They were seeking land for their members whose wagons were close behind. After Perry’s vivid description of “his valley,” the scouts walked up the Little Sioux River. They chose a site on the west side of the river, northeast of the present city of Cherokee. Enough land was preempted so that each of the thirteen Milford colonists who came in 1856, two of them with families of children, had a town lot, a wood lot and acreage for farming. Another group of ten men led by George Banister settled several miles south the same summer.
The first town called Cherokee, later known as "Old Cherokee", was founded in December 1857 just north of the present county seat on the west side of the Little Sioux River. The first winter was cold and food was scarce. Roving Native Americans visited the cabins and were amazed at the number of whites who had invaded their hunting grounds. They demanded food and killed some of the settlers’ livestock. As they went further north and found more people, the Indians became angry. Perhaps the most colorful story of this conflict is that the Sioux Indian Chief Inkpaduta and the chain of events that led to the Spirit Lake Massacre. Inkpaduta and his band began their journey northward near Smithland, Iowa in the winter of 1857. This renegade band of Indians destroyed settlements all along the Little Sioux River, including the Abbie Gardner Sharp cabin on Lake Okoboji where today a log cabin stands as a memorial near the site of the raid. When reports of the Spirit Lake Massacre were later received in Cherokee, many settlers deserted the village. Later a stockade enclosing a log blockhouse was erected as a protection against the hostile Sioux Indians and settlers became less fearful.
During the Civil War, many county men enlisted and their families withdrew to more populated areas. After the war they came back to their land and homes.
The promise of a railroad from Fort Dodge to Sioux City running through Cherokee brought many businesses and professional people during the late 1860’s. The railroad was finally completed in 1870. It did not cross the Little Sioux where expected, although speculators had built up quite a town near the bridge built by the early colonists. In the spring of 1870, these folks moved about a mile and a half to the new depot the railroad had set up, dragging houses, shops, and their county courthouse with them. There were not over ten houses in “New Cherokee” prior to that time. Cherokee was incorporated on April 5, 1873.