This magnificent geological formation was first discovered in 1729 by a French explorer M. deLery. Travelers along the Ohio River, which runs in front of the opening, would seek shelter here, but after the Revolutionary War it became a robber’s lair.
Samuel Mason, once an officer in George Washington’s army, made the cave a tavern, called Cave-in-Rock, which fronted his nefarios exploits. He would send his men up-river to befriend the unwary travelers and offer to act guide. As their boats neared the entrance to the Cave, the henchmen would disable the boats forcing them to drift near the mouth of the Cave. The pioneers were robbed and most often murdered.
In the early 1800’s, the Cave came into the possession of the Harpe Brothers, who had escaped and were fleeing from execution in Kentucky. ” They continued their personal reign of thievery and murder in Illinois, using the cave as a hideout and headquarters until they too, were killed.” (1)
A counterfeiting business occupied the Cave for a time, and numerous other bandits conducted their operations from there.
Afterwards, the Cave continued to provide shelter for settlers heading west. Towns in the area sprang up and local law had driven away most of the known “river-rats”. (1)
In 1929, Illinois purchased the 64 and 1/2 acres surrounding the Cave and designated the area a State Park. The Cave was used as a movie backdrop in a scene from “How The West Was Won,” accurately depicting its use by bandits and murderers in the 18th and 19th centuries.
At the beginning of the 19th century, another group of thieves became occupants of the Cave. After the assassination of Mason, James Ford became its tenant. Ford knew first-hand about the reputation of this piece of real estate and chose to set up shop as Mason had done with the same motos-operendi. Ford, however, hid his actions behind the guise of Sheriff and Ferry Operator.
Ford had been elected a delegate to the Tennessee Constitutional Convention in 1795 and attended in 1796. “He was Captain of the Livingston County Cavalry of the 24th Regiment of Kentucky Militia from July 1, 1799 to Dec. 15, 1802.” (2) He was justice of the peace of Deer Creek, Livingston Co., Kentucky in 1803. In May 1809, the acting Governor of Illinois appointed him justice of the peace for Randolph County. He was removed by the territorial Governor in September of 1809. He was then authorized to administer oaths of office and became overseer of the poor Grand Pierre, Illinois. “Captain of the Grand Pierre area Militia, 4th Regiment of Illinois Territory Militia, Jan. 2, 1810. Promoted to one of the two major positions in the 4th Regiment on Nov. 28, 1811.” (2) He “operated Frazer’s old salt works at the Lower Lick in the 1820’s.” (2) (He was married to Elizabeth Frazer, widow of James Frazer.) Oct. 6, 1823 he was given the authority to operate a ferry at the mouth of Crooked Creek, above Cave-in-Rock, where the Cumberland River meets the Ohio River. He came the sheriff of Livingston Co., Kentucky in Feb. of 1825.
James Ford built and maintained a road on either side of his ferry, up-stream from the Cave. When other men would try to operate similar services to cross the Ohio River, Ford eliminated his competition by blocking the road with felled trees and intimidating them through his henchmen.
Ford became very wealthy from his take of the booty. Records from Livingston Co., Kentucky show he owned 1,800 acres of land. He loaned out money at exorbitant rates. He also kept a hotel run by a couple named Pott.
Ford’s men would guide the travelers to the hotel, rob and often murder them in their beds, or the soon to be victims would board the ferry to be taken to the other side. If Ford thought the travelers had money or goods of worth, he would indicate this to one of his gang and they would relieve them of their valuables on the other side. However, those of minimal means were not bothered.
Sometimes one of his men might be recognized and Ford sent him away for awhile. “One day as Mr. Pott’s son was robbing a man, two farmers saw him and told the police. Ford, realizing that one of his men had been seen in the act, advised the young Pott to leave and then spread rumors that he had ‘ran out the thief’ in order to keep the road safe. Many years passed and young Pott grew a beard, gained weight and changed his appearance so greatly that nobody would recognize him. He returned home on the road and met some ‘strangers.’ It took much convincing to satisfy his past accomplices that he was indeed their old partner. That night he went to the inn, but did not say who he was. He had become rich and gave his father his money to watch. When young Pott went out to the well to get a drink” his father killed him and buried the body. “The next day the gang told the older Pott’s the story of how they had seen Pott’s son. When they described the man, his father realized it was the man he killed. At first they thought it was just a friend of young Pott’s , but when Mrs. Pott’s remembered a birthmark, the body was dug up and the birthmark was found.” (3) After it was realized who had been murdered, the Potts left the inn. It has been said, bones have been dug up in nearby fields and blood stains were still on the walls and floors of the old building. No one knows how many travelers were killed there. When friends and family members traced the routes of their loved-ones, the trail went cold at the inn.
“Ford and his gang caught some travelers once and confiscated their belongings. For some reason, they let a young doctor, who was headed for St. Louis to set up practice, go free. They put him in a boat, told him to get down and not raise up until a time specified by the gangsters. Among the things taken from the party was a mandolin belonging to the young doctor. Finally he landed against the Kentucky shore. He started out through the country until finally a beautiful young lady driving a buggy came long and insisted she be allowed to help him. He was hungry, tired and dirty. She took him to her home and the first thing he saw was his mandolin. He was curious, but didn’t ask question. Not knowing who he had run into at Cave-in-Rock or really what he was into, he kept his cool and let things work out themselves. He was treated so well that he stayed around and set up practice at Salem, Ky., being the first medical doctor the town ever had. Also, he fell in love with the beautiful young lady and they were married. Who was the girl? None other than Ford’s daughter,” (4) Cassandra.
The young doctor? Charles Henry Webb, Jr. He was the great-grandson of James and Agnes (Todd) Ware. His parents were Charles Henry and Mary (Ware) Webb.
Two separate accounts have been given with regard to what exactly brought about Ford’s end. It has been stated Ford and and the father-in-law of a man named Simpson had feuded for years and when Ford killed the man, Simpson set out to avenge the murder. “Simpson gathered a crowd of friends, and went armed to Ford’s house for the purpose of killing him. They found him on the Illinois side loading a boat. He knew at once why they had some, begged for his life, and appealed for protection to one of their number, Jonathan Brown by name. Brown was touched by the appeal, and interceded for the terrified murderer. The plea was so far successful that the crowd waited two or three hours, but when darkness came, they took him out and shot him dead, when he was begging hardest to be spared. It is said that none of the crowd proper did the shooting, but that Simpson compelled his negro to do the deed.” (5)
Another account states citizens of the various surrounding communities finally figured out who was in charge of the events at the Cave and the hotel and sent Regulators to apprehend him. “On July 5, 1833 at Ford’s plantation, the Regulators paid Ford a visit. They ordered Ford to hitch up his wagon and get to a small house down the road. Ford knew what was happending but didn’t act as though he was bothered at all by the circumstances. Ford sat in a chair in the dogtrot of the house. A man loaded a gun inside the room of the house and aimed the rifle through the logs of the wall. Ford made a statement to a slave by saying, ‘I guess I’ll eat my supper tonight in hell.’ ” (6)
Ford was a large, tall man weighing over 300 pounds. It took two days to build a coffin large enough to hold his body. When it was finished, slaves struggled to load the coffin into an awaiting wagon. The burial site was up a steep hill and the coffin slipped out of the wagon and onto the ground. The slaves were instructed to carry it the rest of the way. Dr. Charles Webb, his wife Cassandra, a few slaves and a minister were present at the graveside. As the coffin was being lowered by the straps around it into the grave, a clap of thunder broke, frightening one of the slaves who dropped the front strap. The coffin plunged head-first into the grave. The storm was worsening and it was decided to bury Ford standing on his head. “Supposedly one of the slaves remarked afterward that he thought that this was a good way to bury him, so he could go into hell head first.” (4)
He is buried at Tolu cemetery in Kentucky.
Ford’s children became wealthy. For years, graves were found on Ford’s plantation.
Sources: Judy Ware for all the information and connection to the Ware Family Tree.
Judy Ware for the photos. Cassandra being given to her by Sandra Walker.
(1) Cave-in-Rock IL.jpeg – Wikipedia
(2) Rouge’s Gallery by John Musgrave, Hardin Co. ILGenWeb Coodinator
(4) wklb_chap1 Hell on the Ohio
(5) http://www.microforce.com/htmlpage/logan5.html 
(6) James Ford: Man of mystery playing both sides of the law, by W.B. Jones, Robertson County Historical Society
Other Source: James Ford: ‘Satan’s Ferryman’ and ‘Outlaw of Cave-in-Rock’ by Jon Musgrave, Southern Illinois History Page