The first bridge over the Choptank River at Denton was a narrow one-lane iron bridge with a twenty-six foot long "pivot draw" swing span. "The President and Directors of Denton Bridge Company" was incorporated in 1811 to construct this toll drawbridge by an Act passed by the Maryland General Assembly. The Act "declared to be the sum of three thousand dollars to be divided into six hundred shares of five dollars each." The "causeway" authorized by the 1792 Assembly was constructed to provide a passable road over the marsh to the wharf and this "causeway" was later used for the road to the bridge. The bridge was under construction and referred to as "well advanced" in November 1811. The Levy Court paid $280 per year to allow Caroline County residents free crossings while non-Caroline County residents paid 25 cents for a four wheel vehicle, 12.5 cents for a two-wheeled vehicle, and 6.25 cents for a horse and rider, 3 cents for each mule or horse, and 2 cents for each foot passenger. In 1818 the toll was doubled.
In 1849 the citizens successfully petitioned the General Assembly to enable the Levy Court to buy and make the bridge public and remove the toll. Soon after, the bridge was either rebuilt or completely overhauled. In 1875 a new iron bridge was built. The bridge was described in 1879 as an "iron draw bridge" with a draw of 55 feet. Apparently this bridge had no side rails until the new 1913 bridge was built.
This iron bridge, which had a narrow swing span, was replaced by the a concrete drawbridge (1913- 1980). The 1913 drawbridge consisted of one 16-foot steel girder span and one 19 foot and four 26-foot concrete girder spans, with a concrete overhead counterweight single leaf bascule of 59 feet span. The drawspan was stiffened by a modified warren truss that connected directly to the counterweight.
The bridge tender's house was located about six or seven hundred feet northwest of the bridge, in West Denton, with no direct connection to the former bridge structure. Sam Ewing was the bridge tender. He lived in West Denton at the bridge tender's house and listened for the sound of a horn blown by vessels wanting to pass. The bridge "draw" was electrically operated but required manual operation of the controls. In later years automatic controls with built-in safety overrides were installed. Electric gates with flashing lights at both ends of the bridge replaced the chain that was fastened across the approaches to stop vehicle traffic.
The concrete drawbridge was rebuilt and upgraded in 1945, 1961 and 1976. There were only two other overhead counterweight bridges surveyed in Maryland in 1980-81: Tilghman Island and the College Creek span in Annapolis. Moveable bridges are rare and disappearing rapidly. The 1913 bridge was replaced in 1980 by a fixed high span bridge slightly to the south.