As a deep-water tributary of the Chesapeake Bay, the Choptank River was 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 too. Later, thousands of enslaved people were shipped from Long Wharf to plantations in the South. Ironically, the Choptank River also served as a route to freedom as part of the Underground Railroad. Enslaved people fleeing on foot knew to follow the river’s course north to headwaters in Delaware, and some escapees hid aboard vessels, aided by captains or crewman willing to take the risk. Penalties for assisting runaways were steep, and when suspected Underground Railroad agent Hugh Haziett arrived here from Denton to stand trial for assisting runaway slaves, his boat was met by an angry mob. Found guilty, Haziett received a sentence of forty-four years in prison.