After the election, Davis helped establish Davis & Elkins College, and he died in 1916. Henry Gassaway Davis was born near Woodstock, Howard County, Maryland, the son of Louisa Warfield (née Brown; March 10, 1799 – July 23, 1868) and merchant Caleb Dorsey Davis (March 3, 1792 – September 4, 1850). He was the great-great-great-grandson of Maryland pioneer Thomas Davis, and the great-great-great-great-grandson of Maryland politician and justice Colonel Nicholas Gassaway, both of whom were of Welsh ancestry and emigrated to Maryland in the mid 17th century. Stage coaches stopped at Woodstock five days a week en route to Washington, D.C., and Davis later often recalled one of his earliest memories--witnessing the groundbreaking of the county's first railroad in Baltimore from atop his father's shoulders on July 4, 1828. He had three brothers and a sister. His father's business prospered until he won a contract to grade a section of road between Baltimore and Frederick, Maryland, which caused heavy losses. Creditors caused even the family's horses and carriages to be sold, which proved devastating to Caleb Davis's health. When his family's finances collapsed, Davis (then 15 years old) abandoned his education and took a job carrying water for workmen at a nearby quarry, then became caretaker of "Waverly" a nearby farm own by Governor Howard. When Davis was 20, the B&O completed track from Frederick to Cumberland, and needed men to run the trains and handle cargo. Thus Davis went to work for the Baltimore and Ohio Railroad as a brakeman. His hard work and enthusiasm drew the attention of the railroad's president, Thomas Swann, who promoted him to freight conductor, then passenger conductor. Davis met many statesmen, including Senators Henry Clay of Kentucky (whom Davis came to admire and received invitations to visit at his home in Ashland, Kentucky), Thomas Benton of Missouri, Louis Cass of Michigan, Benjamin Wade and Thomas Corwin of Ohio, and Stephen A. Douglas of Illinois -- all of whom embarked the B&O train in Cumberland to reach Washington, D.C. (or disembarked on the reverse route). Davis also often stayed at a hotel in Washington between trips, and conversed with other notables, including Senators William C. Rives of Virginia, John C. Calhoun of South Carolina and Daniel Webster of Massachusetts. When the B&O finally completed track to Wheeling on the navigable Ohio River, Davis was put in charge of the Piedmont station.