The town of Bridgeport had its beginning in pre-American Revolutionary War times. In 1764, John Simpson entered the area and gave his name to Simpson Creek. Bridgeport was chartered in 1816. When the town was incorporated in 1887, it established the office of mayor and town council. The city currently employs a City Manager. Bridgeport is home to Meadowbrook Mall, a 100-store regional shopping complex serving North-Central West Virginia.
When John Simpson entered the Bridgeport area in 1764, he was attracted by the plentiful supply of fur-bearing animals. The men to follow him were also trappers and the fur trade was the first business in what is now Bridgeport. As the settlers came and cleared land, timber was sold, and the lumber trade became another area business.
The first mill of which there is official record is the Bridgeport or Johnson Mill, which Harvey W. Harmer describes as the first mill in Bridgeport in his Old Grist Mills of Harrison County. This gristmill was constructed by James Anderson sometime between 1771 and 1787 on Simpson Creek.
In the 19th century, farming was the main livelihood, and the stores in town were mostly general stores designed to serve the area farmers. The town also had a blacksmith and a barber (a man born in slavery), several mills, and two hotels. The Baltimore and Ohio Railroad ran through Bridgeport beginning in 1856, eliminating the need for area cattleman to drive their livestock all the way to Baltimore. They instead drove their herds into Bridgeport to the stock pens at the railroad depot. The stockyards remained until the early 1980s when it was raised and replaced by Rite Aid. Cattle, sheep, hogs, and even turkeys were driven into Bridgeport from area farms to be sold here or driven on to market.
The Bridgeport Lamp Chimney Company was succeeded by the Master Glass Company. The Master Glass Company, a marble factory, moved to Bridgeport in 1941 and in 1950 took over the assets of the Akro-Agate Marble Company of Clarksburg. The company manufactured "glass balls for industrial use, colored signal lenses, toy marbles, glass ball reflectors used in highway signs and guard rail posts, and other products for various industrial uses." The company ceased operations in 1973, and the City of Bridgeport bought the property. The building has been torn down, and the former site of the tannery, lamp chimney factory, and marble factory is now a parking lot for the Benedum Civic Center.
On June 29, 2006, the city became noted as the site of a showdown over the issue of separation of church and state in the United States. A portrait of Jesus originally hung on a wall at Bridgeport High School. Two parents filed suit in federal court to have the portrait removed, after the Harrison County Board of Education deadlocked over whether to remove the portrait. The portrait of Jesus was stolen from Bridgeport High School early in the morning on August 17, 2006 and a mirror was put in its place.