Farther south than Richmond, Virginia, Cairo (CARE-o), a city of magnolia trees, is located at the confluence of the Ohio and Mississippi rivers. Settlement was attempted in 1818 by a St. Louis merchant who named the site Cairo because he thought it resembled the Egyptian capital. Cairo and the southern tip of Illinois are still locally referred to as "Little Egypt."

Dominating rail and river traffic, spearheading the thrust of free territory into the South, and harboring citizens with Southern sympathies, strategic Cairo was immediately fortified after the outbreak of the Civil War. Cairo served as headquarters, fortress, supply depot, and hospital for Grant's Army of the Tennessee. After the Civil War, the town had the highest per capita commercial valuation in the United States. Rich with war profits, citizens lavished money on both public and private building projects that, according to the National Register of Historic Places, remain "individual works of architectural brilliance."

Bridges at Cairo connect three states: Illinois, Missouri, and Kentucky. Local legend has it that a penny tossed into the confluence of the rivers at Point Cairo will bring one back again. The levee, rising from the river delta, and the streets along it retain the flavor of the steamboat era.