In April or May, 1776, John Conway Jr. enlisted in the militia, in a company formed by Capt. James Newell. His entire six month term was served in Montgomery County, Virginia guarding Chiswell’s lead mines from the British and Indians. The lead mines at Ft. Chiswell were an important source of lead for ammunition during the Revolutionary War. In May of 1777 he enlisted for a term of eighteen months in a company formed for the defense of the early emigrants to Kentucky. He served the entire term guarding the fort at Boonsborough. During this time Fort Boonsborough was besieged by the British and Indians After nine days and nights they abandoned the siege. Capt. Daniel Boone was present and one of the commanders.

After his discharge at Boonsborough, John Conway Jr. returned to Virginia and, in 1779, he, with his father and mother, one married sister Elizabeth Daughtery, his sisters Nancy and Sarah and youngest brother Joseph, together with several other families immigrated to Kentucky and settled at Ruddle’s Station in what is now Bourbon County. Ruddle’s Station, also known as Hinkston’s station, was located on the east bank of South Licking River, immediately on the Buffalo Trace running to Lower Blue Licks. The settlers farmed during intervals of peace and took refuge within the fort when the Indians became hostile.

One morning, in June 1780, Joseph Conway and two of his young companions left the fort early to drive the cows in for milking. The cows were found on the opposite side of the river, which was a shallow stream at this point. Before the boys could get back across the river, Joseph was shot and scalped by an Indian. His two companions escaped unharmed. An unsuccessful attempt was made to apprehend the Indian responsible for the attack. Young Joseph’s head bled profusely. A poultice, made of cobwebs, was applied to his head to stop the bleeding. Joseph Conway survived and made a complete recovery from his wounds.

A few days after the attack on Joseph Conway, Ruddle’s Station was attacked by a force of approximately one thousand men. These forces, under the command of Captain Henry Byrd, were comprised primarily of Indians, of various tribes, and a small contingent of British and Canadian troops. They were equipped with cannon, and as the fort was not sturdy enough to withstand cannon fire, the settlers were forced to surrender. Before surrendering the settlers had been promised, by Captain Byrd, that they would be under the jurisdiction of the British troops. However, when the gates of the fort were opened, the Indians fell upon the settlers and several were killed before the Indians were brought under control.

The prisoners from Ruddle’s Station and nearby Martin’s Station, which was attacked a few days later, numbered over four hundred fifty. The prisoners were marched to the British military post at Detroit. This journey took over six weeks. There was very little food and they were treated cruelly by their captors. Those who faltered along the way were killed or left to perish.

Among the prisoners from Ruddle’s Station were John and Elizabeth Conway, their sons John Jr., age 21, and Joseph, age 16. Their three youngest daughters, Elizabeth, age 20, Nancy, age 10, and Sarah “Sally”, age 7, were also taken prisoner. Sarah Conway, as were most children her age, was separated from her family and “adopted” by an Indian couple.