Cave-in-Rock nests on the lower banks of the Ohio River, surrounded by fairly dense woodland and numerous cliffs and bluffs. The Ohio River in the late-eighteenth century and early-nineteenth century was a common route used to settle western Kentucky and southern Illinois, as well as to transport goods to New Orleans. Travelers from the East packed up their family, furniture, farm equipment, and slaves on flat boats to move to new homes in the wilderness. This caused dense traffic in the Cave-in-Rock area and spawned river pirates. Pirates preyed on the boats traveling past the fifty-foot cave known as Cave-in-Rock. Its high elevation gave them a good vantage point to see boats coming down the river. The massive cave also baited travelers to come take a closer look, providing opportunity for the pirates to come out, steal the travelers' boats, and kill them. These activities were the work of three notorious pirate gangs: The Jim Wilson Family, The Mason Gang, and the Harpes.
Around the turn of the nineteenth century a man named Jim Wilson brought his family to the cave. He had discovered this cave before when he was on his flat boat looking for shelter during a heavy storm. He brought many liquors and provisions to start a tavern, and within one night transformed it into "Wilson's Liquor Vault and House of Entertainment." The place became known as a rough spot that attracted many gamblers and thieves. These people formed the basis of Wilson's gang of robbers and murderers. The tavern was used to attract passersby who were robbed and killed by Wilson's gang. As boats came by the cave they were captured, their cargo stolen, and the crew killed. The new pilots would sail the boats to New Orleans where the cargo was converted into cash. Suspicion regarding the cave grew because many valuable cargoes that left the port on the upper Ohio were never heard from or seen again. Speculation regarding the cause of these disappearances caused many of Wilson's men to flee; others were arrested. Wilson himself ended up being killed by his own men in exchange for a reward.
The death of Wilson allowed a second outlaw, Samuel Mason, to take over the tavern and change its name to "Cave-in-Rock." Although he came from a good family, was a former officer in George Washington's army, and was recognized as an intelligent
man, Mason nonetheless got caught up in the business of pirating. He used his intelligence to create accidents that intentionally grounded ships. Mason used an eight-mile channel that ran two miles below Cave-in-Rock to his advantage because it was difficult to steer through. Mason's men posed as pilots to help steer ships through the channel, and then grounded the boats and raided them. Women also assisted Mason in his crimes. Wilson had them wait at a place called Diamond Island and ask passersby to pick them up. They then asked to be taken to the tavern where Mason and the gang waited. Mason's career was finally ended when he was killed by some of his gang for a reward of one thousand dollars.
The third and most atrocious group of bandits to haunt the Cave-in-Rock area were the Harpe brothers. They were infamous for the multitudes of unprovoked murders they committed in the Cave-in-Rock area. Micajah, the oldest, was known as Big Harpe, and his younger brother, Wiley, was known as Little Harpe. Originally from Tennessee, the brothers were imprisoned for murder. However, they managed to escape and sought refuge at Cave-in-Rock. Waiting for them were sisters Susan and Betsy Roberts, along with the babies they bore while the brothers were in prison. The Harpes joined the other outlaws in robbing travelers; however, the brothers were much more violent. They were always ready for bloodshed and were armed even while they slept. They took great pleasure in hurting others and once pushed a couple of travelers off a cliff just for the fun of it. The Harpes later went back to the cave
This view inside the cave reveals the roomy interior afforded
to joke about their "prank" but the other outlaws were not amused. The Harpes also captured some travelers going down the Ohio on a flat boat. They killed most of them; however, the two or three travelers who were not killed in the robbery were brought ashore. The Harpes took one of the captives, blindfolded him, and tied him to a horse. They then scared the horse off a bluff more than a hundred feet high. The family got to stay just a few days because the other outlaws drove them out of the cave for being so horrid. The outlaws would have probably killed them if it had not been for their wives and children. However, Big Harpe was eventually killed and beheaded while attempting to flee from jail.
The Cave-in-Rock area continues to be influenced by the history of the river pirates and the gangs. For instance, the road where Big Harpe's head was displayed as a warning to other outlaws is now known as "Harpe's Head Road." The place where Big Harpe was found dead is now known as "Harpe's Hill." The large isolated rock where the Harpes camped is now known as "Harpe's House," and the legend of the Harpe family is told around many places in the Cave-in-Rock area. Today Cave-in-Rock continues to be a popular tourist attraction for people who are interested in the cave's long history and its vast beauty.—[From: J. W. M. Breazeale, Life As It Is; Lois A. Carrier, Illinois; Robert M. Coates, The Outlaw Years; Judy Magee, Cavern of Crime; Otto A. Robert, The Outlaws of Cave-in-Rock.]