Owen participated in his father's raid on Harpers Ferry in 1859. He was guarding weapons at the Kennedy Farm, in Maryland, and did not enter Harpers Ferry itself. When the raid failed he escaped capture and underwent what has been called "the most difficult and tedious flight that ever occurred in this country". After weeks of hiding and travelling at night, living on uncooked corn taken from fields and nearly starving, his shoes having given out, he arrived at Crawford County, Pennsylvania, where he had lived as a child (see John Brown (abolitionist)#Time in Pennsylvania). There he was fed and helped recuperate by a Quaker who remembered his father. Now near the Ohio border, he reached the safety of the home of his brother John Jr., at that time in Ashtabula County, Ohio, some from Harpers Ferry.