In the early 1800s Maryland's roads west were impassable much of the year. President Thomas Jefferson signed legislation in 1806 authorizing the Federal Government to construct the National Road from Cumberland to Wheeling, where travelers could take the Ohio River west. Cumberland was the eastern terminus because at the time, it was the closest that ships on the Potomac River could take travelers to the Northwest Territory (the land north of the Ohio River, east of the Mississippi River).
It was up to Maryland to build a road connecting the seaport of Baltimore to the National Road in Cumberland. Because of the expense of building such a road through Maryland's mountains the banks agreed to provide the funding through the purchase of stock in the Cumberland Turnpike Company in exchange for extension of their charters to 1835. Thus, the Maryland extension from Baltimore to Cumberland became known as the Bank Road. The "Bank Road" reached Cumberland in 1820, with only a few gaps from Cumberland to Baltimore.
One of the gaps was a 10-mile section between Hagerstown and Boonsboro. A turnpike company was formed to close the gap, with the banks again buying the stock in exchange for another extension of their charters (to 1845). This section of the Bank Road has the distinction of being the first use in the United States of the principles of road building conceived by John Loudon McAdam, whose name gave the pavement its name, macadam. According to historian Albert Rose:
The work consisted of resurfacing a former county road. This section was in a sad state of deterioration. The surfacing was completed in 1823.
Soon, Conestoga wagons were carrying wheat, corn, and pork from the West to Baltimore, and returning with manufactured goods needed in the Ohio Valley. The advantages, however, of overland travel were threatened when New York's Erie Canal opened in 1825 and drew the western trade to the harbor at New York City. To compete with the canal for the western commerce, a group in Baltimore received a charter in February 1827 for the Baltimore and Ohio Railroad Company. The railroad reached Cumberland in 1842 and Chicago in 1874, enabling the city to retain its hold on at least some of the western market.