Like most of the original colonies, Virginia had very vague definitions of its boundaries, so it sprawled...in the years of the Jamestown settlement, it went from South Carolina to Maine, and very far west...in theory, all the way to the Mississippi River, up to what's now the northern boundary of Minnesota. . As more colonies were granted charters, those boundaries were pruned back on the Atlantic coast, resulting in states like Pennsylvania, Maryland, etc.. The northwestern limit was pulled back after the Revolutionary War by the Northwest Ordnance of 1784, which mostly threw out the large overlapping claims by the eastern states on the northwestern territories, allowing the new territory to become new states. With that, Virginia extended only to the Ohio River. But not for long: Kentucky was split off, in 1789, right at the Cumberland Mountains, with the southwestern tip being the Cumberland Gap. Still, Virginia was a rather bulky looking state. Then, because of notions about secession in 1861, eastern Virginia and West Virginia became two states, in 1863. That line at the southwest then moved from the Ohio River down to the Tug Fork River. So, what was a very large plump-looking state in 1784 became, by 1865, something with a skinny foot projecting west.