Before roads were paved or tracks were laid, overland travel was a hazardous proposition, with winter storms turning them into mud paths impassable by even mules. Most people just preferred to sail down the rivers, but in the early days of the United States such an option simply did not exist to travelers wishing to make it out to the West. The newly-settled territory in Ohio was the first to face this problem, with the Allegheny Mountains separating the Potomac from the Ohio River. President George Washington was sure a road needed to connect the two.

On this day, March 29, in 1786 the first surveys began of what would become the Cumberland Road or the Nation Road, now part of Route 40. The route today runs from Baltimore, Maryland through Pennsylvania, West Virginia) to the Ohio river and beyond into Illinois.

In 1803 Congress allocated a part of the revenues from the sale of land in Ohio to the building of the Cumberland road connecting Cumberland in Maryland (on the Potomac River) to Wheeling in what is now West Virginia (on the Ohio River). Work began in 1811 and Wheeling was reached in 1818. Soon after, plans were made to extend both ends of it.