Choptank was called Medford's Wharf prior to 1883 and Choptank Landing after 1883. It is the southernmost village in Caroline County on the Choptank River. Prior to the arrival of the railroad, this landing also served nearby Preston (once called “Snow Hill”), which has been described as a "breeding ground for canners.” Before 1875, the village consisted of only two houses, a store and wharf. But by 1880, two wharves were present. By the early 20th century, Choptank had four wharves.
J. A. Wright and Brother (1885-1889) operated a cannery at Choptank; and Walter M. Wright & Sons (1900-1924), and William James Wright (1900-1920) each operated a cannery there. The latter canned peas and tomatoes under the "Jim Dandy" and "Dottie Dimples" brands and operated a basket factory.
The landing was busy with the shipping of canned goods from the 31 canneries located in Preston and Choptank. Three steamship companies served this landing in the 1880s. Steamboats served this landing at least from 1883 to 1922, and up to three steamers a day were known to tie up at the wharf until the railroad came to Preston in 1890. A steamboat vacation brochure dated circa 1922 mentions Mrs. Harry R. Nichol's guesthouse capable of accommodating up to six guests.
The village of Choptank was noted for its fisheries - as many as 60,000 herring and shad are reputed to have been caught here in one day. "Black bass" (probably largemouth bass Micropterus salmoides), "yellow bass" (exact species unknown), yellow perch (Perca flavescens), and catfish (Ictaluridae, genus and species unknown) sold to the locals and shipped to Baltimore and Philadelphia. Captain Tom Price built boats in Choptank including the Leon. A yacht basin was built at Choptank in the 1930's as part of a WPA project.