James Cannaday was born in 1750 in Buckingham County, VA.  During the Revolutionary War, Private James Cannaday (recorded as Kennedy) enlisted with the newly-formed 3rd Virginia Regiment. The Regiment was part of the Continental Line.  Gen. Hugh Mercer authorized, and had overall command of, the 3rd. The Regimental commander was Brig. General Weedon, and Captain Wallace was his immediate commanding officer.

James Cannaday’s service under Washington’s command included the New York Campaign, Crossing of the Delaware, the Battles of Trenton and Princeton.  In 1777, he was active in the Battles of Brandywine and Germantown. 

After his service,  he claimed his land bounty and moved to what is now the county line between Floyd and Franklin Counties. It was then part of the newly named Montgomery County.   

James married Elizabeth Raikes, sometime before 1780, presumably during the time of the Revolutionary War. They had a large family and James worked as a farmer the rest of his life. He was often asked to speak about his service in the Revolution, especially the Crossing of the Delaware. He died in 1817 and was a well respected leader of the small community of Endicott, Virginia.

James is buried on a hill near the Runnett Bag Hollow where his farm was located. His large family begat large families for numerous generations and they all stayed in the mountains he had claimed for his service. 

Cannaday is actually the family name, not Kennedy.  Today, if you travel on the Blue Ridge Parkway south of Floyd, Virginia, you will cross Cannaday’s Gap.