The first bridge to span the gorge was an engineering feat for its time, being about 120 feet long with a height above the water of 30 feet. The funds were appropriated in 1832, and construction began in 1833. The stone for the abutments had to be hauled from Abington in the southern part of the county, and all the timbers and bolts were prepared on site. When it was complete it was considered the finest bridge on the National Road. It was closed to traffic in 1895.

The steel Main Street Bridge was completed in June 1897 to specifications laid out in 1896. At that time, the electric-powered interurbans that regularly used the bridge were relatively light, but they did not remain so. Increases in the size and numbers of the trolley cars, as well as an increase in all traffic, contributed to the excess strain on the bridge. Additionally, the electricity that propelled the interurbans was blamed for accelerating the rust that was already present. By 1915, many of the steel girders were visibly corroded, and the city closed the bridge in August.

The next structure to span the Whitewater was the concrete Main Street Bridge. Construction on this bridge started in September 1917, but World War I interrupted the progress by claiming material and labor for war industries. Bridge construction continued intermittently until it was opened in the summer of 1920. This image shows the Municipal Electric Lighting and Power Plant and the old gas works building, which still exists, although badly in need of preservation. This bridge remained in service until it was closed in 2000 when the US 40 Bridge at South A Street opened. It was torn down in 2002 to be rebuilt in the same location and opened in October 2004.

The Doran Bridge was named for the city engineer who designed it and was completed in 1885. It was made primarily of wrought iron and had a total length of 516 feet, reportedly the longest of its kind in the world at the time. It joined North D Street to Richmond Avenue and provided easier access to the suburbs on the west side of the river, encouraging their growth. It remained in service until 1948 when the city finally deemed it unsafe and closed it. It was dismantled in the summer of 1950 and replaced by the Twentieth Century Bridge.

The G Street Bridge was sponsored by the South Side Improvement Association and dedicated in 1932. The group worked for many years to get the bridge built, but the project was postponed many times by other pressing bridge needs elsewhere, most notably the two Main Street Bridges in 1897 and 1917-20.