In addition to his legal practice, Stephenson became politically active, particularly in promoting internal improvements, including the Staunton-Parkersburg Road, the Northwestern Turnpike, the James River and Kanawha Canal, the North Western Virginia Railroad and the Little Kanawha Navigation Company.

Thus he was elected to the Virginia House of Delegates for the final times from the district comprising Wood, Ritchie and Doddridge Counties.

[3] Following Lincoln's election (despite having received only 4% of the vote in northwestern Virginia), on January 1, 1861 Stephenson addressed a large meeting in Parkersburg, as did General John Jay Jackson and Arthur Boreman, and that meeting adopted a resolution both pro-Union and pro-Virginia.

[6] Union troops encamped on the grounds with Stephenson's permission during the American Civil War (after General John Jay Jackson told them to move off his property on Quincy Hill), although later Union cavalry damaged both this mansion and garden.

[7] Stephenson's eldest son, Kenner, enlisted as a private with the 36th Virginia Infantry on April 15, 1862,[8] and this Stephenson also put up the $4000 cash bond for the wife of Confederate Captain Marcellus Clark, who was accused of being a horse thief (and who before the war had helped manage the California House in at Claysville).