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Ripley, a community rich in history, holds a number of prominent residential and commercial buildings which still exist that were once owned by anti-slavery men and women who worked as conductors on the Underground Railroad.

Front Street is probably the most notable section within the historic part of town being comprised of four to five long blocks of elegant homes, several of them once owned by the conductors.

The Liberty Monument at the foot of Main Street on the Ohio River commemorates local antislavery figure Reverend John Rankin and others, such as Colonel James Poage (Ripley's founder), Thomas McCague, Thomas Samuel Kirkpatrick,

John Parker, U.S. Senator Alexander Campbell, and others outside of Ripley who served the fugitive slaves on connecting routes north at Russellville, Decatur, and Sardinia.

Slaves had been escaping to freedom in the North since before the Revolutionary War. Ohio was a particularly desirable haven, because the Ordinance of 1787 prohibited slavery in the Northwest Territory. Escape became more difficult with the passage of the Fugitive Slave Act of 1850. Under this act, slaves captured in free territory could be returned to their masters if ownership could be established.

Abolitionists such as those mentioned earlier devised a variety of ruses to outwit the slave hunters. Secret hiding places were built in houses, barns, and stores. An intricate system of alternate routes was established. Disguises were used, and pursuers were led on fruitless chases by decoys. False information was fed to eager, unsuspecting slave owners. Meanwhile the slave were hidden, fed, clothed, and sent north to Canada.

The abolitionists risked heavy fines and imprisonment, and the Southern slave owners offered rewards for the assassination of better known abolitionists. Such abolitionists included the Reverend John Rankin and the freed slave John Parker.

Ripley is presently known for its Abolitionist activities during the early 1800's and its many interesting shops and river town atmosphere. During the early 1800's, one of its religious leaders was Rev. John Rankin. Rev. Rankin was a staunch abolitionist who along with other abolitionist of the area defied the law to help fugitive slaves escape from their bondage. "Eliza" from the famed book called "Uncle Tom's Cabin" crossed the Ohio River into safety. The story within the book was based upon a true incident which involved a runaway slave who escaped and crossed the Ohio River into Ripley and made her way to freedom. Other stories of abolitionist activities involve a free black man, John Parker,  who maintained a thriving business within Ripley. His business was one of the largest within town and he was known to help escaped slaves to freedom.

One residence on Front Street, which heralds undocumented fame, is the Signal House owned by Vic and Betsy Billingsley. A lantern in the attic signaled Rev. Rankin that the waterfront was safe to transport slaves to freedom.

Other prominent properties include the Campbell home at 114 Front. The site of the Beasley home was at 124-28 Front, currently 136 Front Street. Both the Rankin and Parker House have been accorded National Historic Landmark status.

During the Civil War, Ripley citizens responded with patriotic pride to defend its nation against its aggressors. Several companies of men were recruited to join volunteer regiments being formed at Columbus and Camp Dennison, Ohio. These troops would eventually fight in the West Virginia and Virginia Campaigns, while others followed the Ohio Department under Generals Rosecrans, Howard, Thomas, and Sherman south into the very heart of Dixie.

Other companies were raised from local townspeople when the need arose for defense. These companies fought in Augusta, Kentucky, when General Morgan made his 1862 raid into Northern Kentucky; and again in 1863 when Morgan's troops came within 1mile of the village limits. These same companies had volunteers join the 100 days men when troops were needed to relieve regular forces for the final drive into Virginia to defeat General Lee.