Flickr via Vincent Parsons
Borrowing its name from the Osage and the Pottawatomie people who once lived in the area, this town, which now has 4,308 residents, was the site of the Battle of Osawatomie in 1856, an important precursor to the Civil War. The battle was marked by abolitionist John Brown's unsuccessful stand against the Border Ruffians, but his brave efforts are commemorated at the hill where he fought, now known as John Brown Memorial Park.
Related: 25 Tiny Towns to Visit for a Glimpse at How We Used to Live