In 1760, Talbot County resident Deborah Nichols was licensed to operate a ferry near the lost town of Dover, reflecting the common practice of women taking over ferry operations after their husbands died. In 1765, Caroline County resident Henry Troth began operating a second ferry north of the Dover Ferry's crossing by constructing a causeway through the marsh, and in 1786 the Dover Ferry's route was transferred north to Troth's crossing, ending service from Barkers Landing near Dover. Between 1810 and 1811, the first Dover Bridge was built, 1200 feet long on oak piles with a pine deck and railing and a 50-foot-wide draw. In 1860 and 1861, Caroline and Talbot Counties appropriated $8,540.83 for a new Dover Bridge. After decades of disruptive repairs, a three-span iron bridge replaced the second Dover Bridge in 1898. In 1900, the bridge's wooden draw was destroyed when a traction engine crashed through it and sank to the bottom of the Choptank River, and a boat temporarily carried wagons and horses across the river. In 1909, Talbot and Caroline County Commissioners announced plans to rebuild the bridge again, and in 1912 the counties constructed a 515-long iron truss bridge as the fourth Dover Bridge. In 1931, the State Roads Commission appropriated funds to rebuild the Eastern Shore's unsafe and narrow bridges, including Dover Bridge, as the region had become heavily reliant on automobile transportation for shipping agricultural products and seafood to markets. In 1933, the fifth Dover Bridge was completed with a rare design combining elements of a movable swing span and a metal Warren truss bridge. In 2017, the sixth Dover Bridge became a high-level fixed span that does not disrupt automobile or boat traffic, while the SHA, successor to the State Roads Commission, preserved the 1933 swing-truss bridge in place for its historic engineering significance.