Gregory enlisted as a private in Co. A of the 3rd VA Cavalry, the Boydton Cavalry, on July 25, 1861. He was taken prisoner at Warrenton, VA on Novemebr 12, 1862 and paroled 2 days later. His horse, valued at $450, was killed on July 1, 1863 at Brandy Station, VA. He was captured on July 5, 1863 near Williamsport, MD. It is unknown when and where he was imprisoned, but he is listed in the company rolls as absent into the fall of 1863 and as present by March, 1864. He was again captured on May 11, 1864 at Beaver Dam, VA and sent to the military prison at Fort Monroe, VA. On May 16, 1864, he was sent to the prison camp at Point Lookout, MD. He remained there until exchanged on March 15, 1865 at Aiken's Landing, VA. He took the oath of allegiance in Richmond, VA on June 6, 1865.
Gregory is listed as a farmer in Boydton, VA in the 1870 census, living in the household of John W. Jones, a former schoolmate who was by then teaching at R-MC. He is a farmer in 1880 and 1900, having married but remaining in Mecklenburg County, VA. He was a music teacher in the 1910 census.
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