Historical Marker #68 in Maysville commemorates the founding of that Mason County city.

Originally called Limestone and located on the Ohio River, Maysville, like Cumberland Gap in the Appalachian Mountains, was a natural avenue for the earliest settlers to enter Kentucky.

In later years, African American slaves also sought freedom and opportunity by way of Maysville. Because of its location on the Ohio River, the town was in close proximity to several Underground Railroad operatives. These included Presbyterian minister John Rankin, African American mechanic John Parker, and others in Ripley, Ohio. Therefore, Maysville served as an important crossing point for Kentucky slaves to escape into the free state of Ohio and on to Canada.

Maysville figured prominently in one of the state's most famous and dramatic antebellum slave escapes. On September 29, 1844, abolitionists Delia Webster and Calvin Fairbank arrived on the Maysville side of the Ohio River. The couple had traveled all night from Lexington. Hidden in their borrowed carriage were the Lexington slaves Lewis Hayden, his wife Harriet, and son Jo. Unable to make previous contact with the Underground Railroad conductor John Rankin, Webster and Fairbank crossed the Ohio River and presented the slaves to anther conductor about four miles north of Ripley. After a harrowing journey, the Hayden family ultimately made their way to freedom in Canada. Webster and Fairbank would not be so fortunate. On their return trip to Lexington the two abolitionists were arrested.

Webster, convicted of "slave stealing," was sentenced to two years in the Kentucky state penitentiary in Frankfort. However, she only spent about two months incarcerated. Fairbank was sentenced to 15 years - five years for each slave - but was pardoned in 1849 by Governor John J. Crittenden. Lewis Hayden eventually moved to Detroit, Michigan, then Boston, Massachusetts, where he ran a successful clothing business and operated the Boston Vigilance Committee, which helped numerous former slaves make their own way to freedom. Delia Webster later continued her Underground Railroad activities in Trimble County before being forced to leave the state. Calvin Fairbank was arrested in 1851 for helping a female slave escape from Louisville to southern Indiana, and was again placed in the state penitentiary where he remained until he was pardoned by Lt. Gov. Richard T. Jacob in 1864.

Therefore, Maysville’s past is intertwined with both pioneer history and the story of anti-slavery advocates.