We do not know much about the early life of Monk Estill. The names of his parent and the time and place of his birth will likely remain a mystery. We do know that he came to Kentucky in the 1770s with his master Captain James Estill. He is credited with the planting of an apple orchard at Boonesboro that the settlers hailed as “a great benefit to the country.” He and his wife, whose name and history also remain a mystery, gave birth to the first African American child born at Boonesboro. The child was named Jerry. During his lifetime, Monk would marry three times and have thirty children.
Monk and his family were moved to Estill’s station in 1780, when his master established his post about 3 miles southeast of what is today Richmond Kentucky. He performed the standard duties of a slave at this time, such as planting and tending crops, and tanning hides. He was also greatly valued for his ability to produce gun powder.
On March 19, 1782, the men of Estill’s fort was on a relief mission to Strode’s Fort, leaving the women, children and slaves behind. The next day, while Monk was out gathering fire wood, he was abducted by a party of Wyandot that had surrounded the station. He managed to convene the Natives that the defenseless station was heavily armed and defended by 40 men who knew of the Wyandot plan to attack. He convinced them to postpone their attack, but not before a young girl, 14 year old Jennie Gass, left the fort’s safety and was killed.
Captain Estill and his men tracked the party of Wyandot’s that have taken Monk captive. They fought the natives in the Battle of Little Mountain or also called Estill’s Defeat. Monk yelled out to the men the number of natives they were facing, and when he was able to get free, he held the horses for Estill’s men as they retreated. During the retreat, Monk rescued James Berry and carried him 25 miles to the station. Captain Estill’s son, Wallace, gave Monk his freedom in 1782, as a reward for his bravery at the Battle of Little Mountain. Monk who became a Baptist minister, is considered to be the first slave freed in Kentucky.