In order to cross the Fox River before the first bridge was built in 1836, citizens had to take a ferry across the river. With the construction of a bridge and a dam, citizens were not only able to cross the river with ease, but were able to run their mills at higher speeds with the power supplied by the rushing water of the dam. The original bridge, which was built of wood, stood eight feet above the water at low tide and 18 feet wide. This bridge was swept away in 1839. The bridge that replaced it was also washed away in 1849. Yet another span was built in 1857.

This would not be the last time the Main Street Bridge failed to survive for an extended period of time. Over the history of the bridge, there have been seven spans constructed. Two of the most famous are those of 1874 and of 1927. King Building Company of Cleveland, Ohio built a new bridge in 1874. Although constructed of iron, the bridge was not meant to handle heavy loads--something that unaware trolley passengers discovered on July 1, 1902. On crossing the bridge from the west, the trolley car with 30 passengers aboard, broke through the bridge and came to rest at a 30 degree angle with its back end in the water. Fortunately, no one was seriously injured in this mishap. Following the accident, workmen erected a footbridge over the river, allowing continued access to the other side of town. The trolley car was not extracted from the its resting place until the following day.

Apparently, citizens had been concerned about the bridge's condition prior to this accident and had alerted city and transit officials of its hazards. Following the accident, many placed blame on the officials who had not heeded their warnings. Reconstruction of the bridge began later that summer. This bridge was paved in 1915.

The improvements made in 1928 were designed by Lester Norris, one of St. Charles' philanthropists. Norris got the inspiration for its design from bridges he saw while on his trips abroad in Italy. Charles Lamb used the sketches made by Norris to construct the bridge. Workers widened and reconstructed the 1902 bridge and added the new embellishments, which included four bronze foxes.

The latest bridge was constructed in 1997. The four bronze foxes that are on the bridge, which were a gift of Herbert Crane in 1927, were cast in France and represent the "Four Sons of Charlemagne"--a story which a former mayor, C.V. Amenoff, wrote.