It fought in the Seven Days' Battles, the conflicts at Gainesville, Second Manassas, Sharpsburg, Fredericksburg, Dumfries, Rapidan Station, Brandy Station, Upperville, Hanover, Gettysburg, Williamsport, Funkstown, Culpeper Court House, Bristoe, Mine Run, The Wilderness, and Todd's Tavern. Later, it skirmished around Richmond and Petersburg, then was active in the Appomattox operations.

After the war, Charles S. Webb studied medicine at the University of Virginia. The following is his obituary.

"Dr. Charles Shepherd Webb, a native and life long resident of Caroline County. and one of its most prominent citizens died at his home in Bowling Green yesterday afternoon after a brief illness. Dr. Webb. who was 89 years of age, was formerly mayor of Bowling Green. He practiced medicine In Caroline County for nearly 60 years. Fellow townspeople regarded him as the foremost citizen in Caroline County, a leader in civic, church, medical and political activities. He was educated at the old Farnham Institute and University of Virginia. Before studying medicine, Dr. Webb was professor of mathematics at Baylor University. Texas, and later principal of a male high school at Camden, Ark. Before coming to Caroline County, Dr. Webb served as professor of medicine in the Southern Methodist College at Atlanta. For the past 50 years he had practiced his profession in Bowling Green. Known to all the people of the county, Dr. Webb was a man held in the highest esteem. He served several terms as Mayor of Bowling Green and otherwise was honored by his fellow citizens. He was married twice, his first wife having been the former Miss Ella Moore Fauntleroy of Atlanta, who died in 1898, and his second wife the former Miss May Camper of Orange County. Dr. Webb is survived by his widow, one daughter, Miss Margaret Shepherd Webb, and three sons, Dr. Charles Shepherd Webb. Jr., Bowling Green; Robert Henry Webb, attorney of Richmond, and Dr. William Camper Webb, of Ashland, Va.
Funeral services will take place Saturday morning at 11 o'clock from the Bowling Green Methodist Church, conducted by the pastor, Rev. L. M. Ritter. Interment will take place In Lakewood Cemetery." (Fredericksburg) The Free Lance-Star - Nov. 29, 1935.