As one of Washington's oldest commercial corridors, Wisconsin Avenue has been a direct route to the Potomac River for more than 250 years. Originally an Indian trail, the route became known as Frederick Pike and linked the small port of George Town (incorporated in 1751) to the county seat of Frederick, Maryland, located 42 miles to the northwest. This was a "rolling road" for the transport of hogsheads — large barrels containing at least one thousand pounds of tobacco which would be shipped to England, Europe and the West Indies.
Tobacco shaped most aspects of life in George Town and was the foundation of its early economy. Before the American Revolution, tobacco was almost the sole currency of the region. Numerous dealings were based upon it: debts, rent, fines, salaries and levies were all paid in tobacco. In 1732, tobacco was made legal tender in Maryland at one penny a pound. An early English writer called tobacco the "meat, drink, clothing and money of the colonists," many of whom saw tobacco as the path to fortune.
"Rolling roads" such as this were the best roads. They were smooth (so that the cask would not be punctured by rocks and tree stumps), dry (to keep the tobacco from getting damp), and reasonably level (to minimize the uphill pull and avoid run-away casks on the down slopes). The large
hogsheads were pulled by oxen or horses and rolled to market by placing an axle through the barrel and attaching wheels. At the time of the American Revolution, the Chesapeake area exported more than one hundred million pounds of tobacco annually, dominating the world market. A large part of that went through George Town, which by the end of the century was the largest tobacco port in the U.S.