The Wharf Connected Leonardtown to the outside world.
Before roads were built, or rails laid for trains, goods and people traveled by ship. In the mid-1600s, ships called directly at the wharves of Maryland plantations to pick up tobacco, the staple crop of the colony, and deliver goods from England and the Caribbean. Before long, Cecil Calvert, Lord Baltimore and Proprietor of the Colony, determined he needed better control over trade to assure more efficient collection of taxes and duties on goods. On November 6, 1685, the Maryland Assembly passed the Town Act, designating certain ports for trade. "Brittons Bay Bayleys or Taunts," eventually named Leonardtown, after the younger brother of Cecil and first governor of Maryland, was one of three ports in St. Mary's County designated as legal for trade.
By 1860, southern Maryland produced the nation's largest tobacco crop and Leonardtown had thirty-five dwellings within its corporate limits. In that year's presidential election voters in St. Mary's County cast 920 votes for John Bell, and one vote for Abraham Lincoln. During the Civil War, despite the presence of Federal Troops bivouacked in Sheep-pen Woods west of town, contraband goods somehow found their way to Leonardtown's Wharf — at least until March, 1864, when Robert Clark and Robert Swann were jailed for smuggling.
Following the Civil War, Captain Asa Lawrence arrive to assume leadership of the Freedman's Bureau. Despite his association with this very unpopular agency of the Reconstruction, Lawrence's able leadership gradually improved life for everyone, black and white, and Lawrence, too, began to prosper. By 1879, Lawrence's brick kiln had become so busy that he was shipping bricks from the Leonardtown Wharf to as far away as North Carolina. In that year, sixty-foot wide, thirty -foot deep channel was dug from Abell's Wharf to Leonardtown to accommodate steamboat traffic, and the steamship Thompson promptly brought the first bicycle to Leonardtown.
While the rest of the country was swept along in the Great Railroad Boom, Leonardtown, like most of Tidewater, was celebrating the Golden Age of Steamboating.
Loker, Aleck; A Most Convenient Place
, Leonardtown,Maryland 1650-1950.
Commissioners of Leonardtown and Solitude Press, 2001, "A Maryland Pilgrimage
."National Geographic Magazine
, February 1927.