Crittenden County was once crossed by the Chickasaw Road, which was a part of the Old Saline Trace. This footpath was used by Native Americans when hunting game that crossed the Ohio River to the salt licks in Illinois. The first settler in the area was James Armstrong, who arrived from South Carolina in 1786 and built a log cabin. His family joined him five years later, along with other families who came to settle there. Early in the nineteenth century, Flynn's Ferry was established where the trail crossed the river.