Denton photograph collection

The town of Denton, located on the east side of the Choptank River on Maryland's Eastern Shore, is the county seat of Caroline County. It was originally named "Edenton" for Sir Robert Eden, proprietary Governor of Maryland in 1769-1774; the "E" was dropped after the Revolution, when Governor Eden left Maryland for England. Denton was established as the county seat of Caroline County in the early 1790s. A courthouse and jail were built ca. 1791, then a causeway was built through the marsh on the east side of the Choptank River with a wharf at the end of the causeway. Soon after that, surveying began for the town proper.

The first bridge over the Choptank River at Denton was built circa 1811, a one-way drawbridge for which a toll was charged to non-residents of Caroline County. It was replaced in 1875 by an iron bridge, which stood until replaced by a concrete structure in 1913. Steamboats began to come up the Choptank River from Baltimore prior to 1850, and Denton became a port for steamers and freighters. Denton's streets remained unpaved into the early 20th century.

The Law Building, built in 1902, was the site of "The Law Building and Realty Company", as well as a post office, hardware store, other offices, lodging, and a law library. The Brick Hotel, built in 1775, was first a tavern and inn. In the early 1900s, it was a place for local men to chat about politics, livestock, and crop prices. It was also the summer home for writer Sophie Kerr Underwood, who came to see friends each year, and may have based her book One Thing is Certain and some of her stories on people in Denton. The Peoples' Bank, organized in 1898, operated in the Masonic Building for a few years, then constructed a building from Indiana limestone saved from the 1904 Baltimore Fire. The Christ Protestant Episcopal Church was built in 1873-1874 by contractor Samuel H. Fluharty.