Cleveland takes its name from General Moses Cleaveland, a surveyor and investor for the Connecticut Land Company who led the first group to settle in the area in 1796. Cleaveland oversaw the planning of the early town, then headed back to Connecticut a few months later and never returned to the town that bears his name.
It’s not exactly clear when the first “a” in his surname got dropped from the city’s name, but one story explains that in 1830 the Cleveland Advertiser was pressed for space on its headline and simply axed the “a.” The change caught on, and the town became known as Cleveland.