Bridgeport had possibilities of becoming an important and progressive town, but two factors (1) physical‚-the Canadian River‚-and (2) human‚- a town feud‚- caused its downfall. Located on the south bank of the Canadian River in an area of rich farming land, and served by crossing rail lines, the town appeared destined to be the chief shipping point for a large area. The Canadian River, approximately one mile wide at Bridgeport, was subject to high water and sometimes flood during the rainy season. When water was low it could be forded, but there was always the problem of quicksand. The town received its name in the 1890s as the place where stagecoaches waited to cross the river. During high water they were ferried across; during low water the teams forded the river, following well-chosen paths carefully but never stopping in the channel. In 1893 a toll bridge was built. In 1895 a store with a post office located at the south end of the bridge, and Bridgeport had its start. In 1915 a free bridge replaced the toll bridge, but a few years later it was damaged by a flood. The bridge was eventually replaced by the Key Bridge, which charged tolls during the first year. In 1932 the Oklahoma Highway Department constructed a bridge downstream from the Key Bridge and rerouted highways to the south of Bridgeport. In 1948 the Key Bridge was partly burned as a result of a grass fire and had to be removed. In 1958 the bridge for Interstate 40 was completed, resulting in the highway being moved more than one mile south of town. There have been at least five high-water and a dozen low-water bridges across the Canadian near Bridgeport.
In 1898 the Choctaw, Oklahoma and Gulf extended its tracks westward and built its bridge near the toll bridge. The Enid and Anadarko Railway north-south lines, built in 1901, used the same bridge. In 1907 the railroad bridge was demolished when a freight car jumped the track and struck a span of the bridge. This train, carrying cars of livestock and household goods belonging to German emigrants, fell into the sandy river bed. The heavily loaded cars Immediately began sinking into the quicksand. Men trying to save the livestock opened the car doors. Out flew ducks, chickens. and geese to the Bridgeport side of the river. The engine, coal car, and caboose were all that was saved. “To this day the other cars with everything inside as well as the middle section of the bridge lie buried deep somewhere in the shifting sand of the Canadian River bed.” The bridge was replaced the next year but in 1914 was washed away during a flood. A new railroad bridge was again built. Later, in 1939, the track south from Bridgeport was abandoned. In 1901, when the Caddo and Wichita lands were opened for settlement, Bridgeport became a booming new tent town. In a short time frame and brick business buildings and good homes replaced the tents, and a town of over three thousand persons had come into existence. Because of the topography and water a feud developed. Chrystobel Poteet, in the article “Bridgeport by the Canadian” (Chronicles of Oklahoma Vol. XXXIX, No. 2) described it:
People found that water on the west side of Bridgeport was clear and pure while that on the east side, where most of the business buildings had been erected, was filled with gypsum crystals. Instead of trying to find a way to bring good water to the east side a bitter feud developed. The depot was the west side near the river but a long hill had to be climbed to reach the post office on the east side. To get mail distributed more conveniently business men on the west side contrived to move the post office one night during dark hours. A two story brick building was erected hurriedly on the west side for a bank. The big three story frame hotel was also moved to a corner location on the west side. Merchants on the east side became so embittered that many of them, in 1902, moved their buildings and stock to Hinton. It is pretty interesting to see buildings that have been abandoned, there is a lot left to wonder, but it is even more crazy when a whole town is practically left behind. Its a weird feeling seeing the amount of belongings left. In between the levels of wear, tear and aging, you can see that the objects were once in good condition, and were once used frequently.
In 1904 Bridgeport had seventy-six places of business, including two banks, a flour mill with an output of one hundred barrels per day, and two hotels. A waterworks had been built along with a forty-thousand-gallon elevated tank. By 1909, however, the number of business institutions had decreased to forty-three. and the population was estimated at less than one thousand. Throughout the years Bridgeport has declined in both population and as a trade center. The changing of the highways resulted in the town being bypassed to the east and south. It is now a somewhat isolated village in which about 30 people live. The only remaining business is a small grocery store. The depot has been removed, and spurs of the primary track are covered by sand and grass. The place has been described as a rural retirement community.