As a deep-water tributary of the Chesapeake Bay, the Choptank River had been a commercial artery of the Eastern Shore since colonial times, with cargoes of timber, tobacco, and farm harvests hoisted by dockworkers to waiting ships. During the early years of the slave trade, captive Africans were unloaded here, and later thousands of enslaved people were shipped from Long Wharf to plantations in the South. Ironically, the river also served as a route to freedom as part of the Underground Railroad, as enslaved people fleeing on foot followed its course north to its headwaters in Delaware, while some escapees hid aboard vessels aided by captains or crewmen willing to take the risk. Penalties for assisting runaways were steep, and when suspected Underground Railroad agent Hugh Hazlett arrived here from Denton to stand trial for assisting runaway slaves, his boat was met by an angry mob. Found guilty, Hazlett received a sentence of 44 years in prison.