The land occupied by today's Elk Landing was initially given by Native Americans to the Swedish settlers in the area for the construction of a trading post in 1655, but it would not be until 1690 that Swede Jon Steelman builds a trading post on the site. In 1735, Zebulon Hollingsworth Sr. begins to purchase the land owned by Steelman and names the location Elk Landing Farm. Zebulon apparently operates an inn or tavern on the property serving those shipping goods through the Elk Landing area. Zebulon Sr. dies in 1763 and ownership passes to his son Zebulon Jr.
Elk landing in this period was becoming the preferred port for travel and shipment of goods between Baltimore and Philadelphia and New York. The Hollingsworths were active in shipping goods and passengers by boat and set up coaches to carry travelers and goods from Elk Landing to and from Baltimore.
Elk Landing played a prominent role in the Revolutionary War. In August of 1777, Colonel Henry Hollingsworth, the Deputy Quartermaster General of the Continental Army provided warning to the Continental Congress in Philadelphia of a large British invasion fleet that was approaching Elk Landing. The British did land over 15,000 troops at Elk landing later that month and Colonel Hollingsworth was responsible for moving large stores of continental army supplies out of the area to keep them from the British. During the colonial army stay at Valley Forge, Colonel Hollingsworth valiantly tried to provide supplies to General Washington's forces, but most of the routes leading to Valley Forge were blocked by British forces.
Elk Landing again played a prominent role at the end of the Revolution. In September of 1781, General Washington arrived at Head of Elk and spent three days thee sending dispatches to his troops. American and French forces were moved by boat from Elk Landing to Williamsburg to prepare for the siege of General Cornwallis and the British forces in Yorktown. American and French forces along with help from the French Navy force the surrender of General Cornwallis in September of 1781, effectively ending the revolutionary was with an American victory.
Following the war, business continued to be good at Elk Landing and Zebulon Jr. built the Stone House that still stands on the property to act as an inn and warehouse for the travelers and their goods coming through the port at Elk Landing. Trade through Elk Landing continued to expand and around 1800 Zebulon Jr. built the current house that stands on the site. The house was originally constructed as a two story structure in the federal style. By 1810 Elk Landing had become the principal port for moving most commodities from Cecil County and for goods traveling to and from the north to Baltimore.
In 1812, war is declared with Great Britain and Elk Landing again has a major role to play. Fort Hollingsworth is constructed near the Stone House, and along with Fort Defiance, located nearby, the two forts are responsible for denying the British the use of Elk Landing for putting troops ashore. In April of 1813, the forts are successful in beating off an attempted British landing, and the British are forced to land troops further down the bay.
Zebulon Hollingsworth dies in 1812 and his widow in 1814, and Elk Landing passes to Zebulon Jr.'s son William. Following the War of 1812, competitive routes began to have an impact on Elk Landing trade and the completion of the railroad through Elkton in 1837 further degraded the attractiveness of Elk Landing for shipment of goods. William dies in 1844 and the property is inherited by his widow Mary. In 1848 a major fire guts the house at Elk Landing, but the building is rebuilt as the three story structure in a Greek revival style that stands on the property today.
The Stone House was placed on the National Register of Historic Places in 1984 and the town of Elkton acquired the property in 1999 from the descendants of the Hollingsworth family. Elk Landing is today operated by the The Historic Elk Landing Foundation and is operated as a living history museum.