Westernport traces its early settlement back to the colonial period before the Revolutionary War. Trappers and hunters in this virgin territory came to trade at the trading post located with a few other log cabins near the mouth of George’s Creek on the Potomac River. In the period after the war, most of the land that is now Westernport was owned by James Morrison and Adam Sigler. Shortly afterwards, Thomas Hammond acquired the west side of George’s Creek, which is now Westernport Hill. These lands were eventually divided and sold as building lots.

The name Westernport derives from the fact that, in the days before there were wagon roads, the early settlers floated their goods and furs on rafts down the Potomac River to Cumberland for trading. Thus it was the farthest port to the west on the Potomac.

Some names of the early settlers who came to this remote area west of Fort Cumberland to make their homes are still common in the town today—Ross, Michael, Poland, Kight, Kalbaugh, Fazenbaker, Broadwater, and Duckworth.

On January 1, 1802, a post office was established in Westernport; it was one of only four post offices in Allegany County at the time.

When Westernport was first incorporated in 1858, the citizens chose a standard commission form of government—a board of five commissioners elected by the citizens, with one of the five selected by the board to serve as its president. In 1904, the charter was changed to provide the present mayor-and-commission format—a mayor and four commissioners all elected directly by the citizens.

The growth of Westernport was relatively slow during the early 1800s due to lack of good transportation. In 1851, the arrival of the Baltimore & Ohio Railroad provided an economical means of shipping coal from the many mines that were being opened. More jobs were created, resulting in an increase in population and an increase in home building. Opening of the West Virginia Pulp and Paper Company nearby in Luke in 1889 was a further boost to Westernport’s economy.

During the 20th century, underlying economic factors changed but the century ended with the town enjoying overall growth and prosperity and providing a favorable environment in which to live and raise families.