The mountainous region of the Allegheny Front (eastern side) of the Appalachian Plateau between an existing canal, railroads and navigable rivers represented a formidable obstacle.

A plan was developed to extend the Virginia Central across the Blue Ridge Mountains and into the Shenandoah Valley and points west.

However, the railroad had found that a planned crossing of the Blue Ridge Mountains at Swift Run Gap was financially unfeasible.

[2] (During the American Civil War, the tunnels were utilized as part of the so-called foot cavalry movements of the Confederate troops of General Stonewall Jackson).

In 1853, the Virginia General Assembly passed legislation authorizing the Board of Public Works to construct a railroad from Covington to the Ohio River.

Planned for future incorporation and sale of stock, the project was called the Covington and Ohio Railroad, but construction was commenced with state funds appropriations.

Prior to 1861, the State had purchased a total of $48,000,000 worth of stock in transportation improvements, many of which were heavily damaged or destroyed during the Civil War.

[5] Huntington was also aware of the potential to ship eastbound coal from West Virginia's untapped natural resources with the completion of the new railroad.

In the 1880s, he oversaw extension of the C&O's new Peninsula Subdivision, which extended from the Church Hill Tunnel in Richmond southeast down the peninsula through Williamsburg to Newport News, where the company developed coal piers on the harbor of Hampton Roads,[6] to extend the C&O to what would become new coal piers at Newport News.