In the early 19th century, competition was fierce among Virginia's port cities to be the point where export products such as tobacco could be transferred to ocean-going and coast-wise shipping.

On December 12 of the same year an eastbound engine of the Portsmouth and Roanoke Railroad pulling 3 passenger cars and 9 lumber cars loaded with cotton struck an upturned end of a split metal rail 2 miles west of the Nottoway River near the present day village of Handsom in Southampton County.

[2] One of the Seaboard and Roanoke's builders from the mid-1830s' was Walter Gwynn, who, during the American Civil War, became a Confederate General assigned to take charge of the defenses of Norfolk, which were held by the southern troops for about a year in 1861–62.

Without a single shot fired, he successfully tricked the small detachment of troops holding the Gosport Shipyard (now Norfolk Navy Yard) into abandoning it for the safety of Union-held Fort Monroe across the harbor.

SCL merged with the Chessie System in 1980, to form CSX Transportation, which is currently one of seven major Class 1 railroads operating in North America in the 21st century.

The circa-1885 Seaboard Passenger Station at Suffolk, Virginia was shared with the coal hauling Virginian Railway when it was built adjacently in the early 20th century.