The mission began in Woodbury, Tennessee, on June 10, 1863, where Morgan had a picket camp. At the start of the mission, Hines only told his men that their mission would be "long and dangerous" and allowed any man who did not wish to go to step out; none did. From there, they traveled through Brownsville, Kentucky, and Elizabethtown, Kentucky. At Brownsville, they stole clothing from a Union sutler, consisting of shirts, trousers, and boots of Union uniforms. At Elizabethtown, the group robbed a train, providing Hines' force with Union currency. When they reached the Ohio River, Hines' then informed his men that they would pose as Union troops under General Jeremiah T. Boyle with orders to pursue deserters, called the Indiana Grays. The crossing occurred between Alton, Indiana, and Tobinsp