ELKTON — Not every Marylander was a patriot, but there are few in the annals of Maryland history who was more divisive in his “loyalties” than Robert Alexander.

Alexander was the owner of a tract in the area that would become Elkton, known as “Friendship,” but his story during the formative years of America shows quite clearly that he certainly was not a true friend of the cause of liberty.

Alexander, a Baltimore lawyer, showed early signs of standing for the cause of Maryland, even joining one of the Sons of Liberty groups in 1766. He advocated for Maryland businesses not transacting business with the accursed stamped paper of Britain, which led to the Stamp Act being repealed by Parliament by March 1766. Three years later, Alexander was part of an association striving to prevent importation and use of goods from Great Britain and another organization resistant to encroachments by the Crown and Parliament.

It was therefore quite logical, once news of the Boston Port Bill reached Maryland, for Alexander to be appointed to represent Maryland in a convention of delegates in Annapolis to decide the course for Maryland and its residents. When the Committee of Safety was organized in July 1775, with eight members from the Eastern Shore and eight from the Western Shore, Alexander was naturally tapped as one of the eight from the Western Shore. He served until he was chosen to serve as a Deputy to the Congress, then sitting in Philadelphia.

Maryland sent word to Alexander there to resist Parliament’s taxation efforts and changes to charters and internal policy, but “in no event” was he to agree to, or unite in, “any treaty or confederation which was likely to result in Independence, without the advice and consent of the Convention.” Alexander was just fine with those policies writing on Jan. 30, 1776, “The instructions of the Convention are come to hand but are not yet laid before the Congress. I am much pleased with them. They entirely coincide with my judgment and that line of conduct which I had determined to pursue — firmness tempered with moderation.”

But things would change that very same year and especially in 1777 for Alexander, who was born at his family’s estate at Head of Elk about 1740, despite having been added to Maryland’s Secret Committee on Jan. 16, 1776, and the Marine Committee in April of the same year, and his subsequent re-election on July 4, 1776, as a delegate.

When the British arrived in Head of Elk — modern Elkton today — in August 1777, they visited with Robert Alexander, only days after Gen. George Washington had visited Alexander. British Gen. William Howe was, in fact, received by Alexander only three days after Washington’s visit.

When the British packed up from their makeshift camp at Elkton they did so with an extra member of their party, one Robert Alexander who went with them north to Philadelphia. He would never return to his Friendship tract in Elkton again.

Indeed by the summer of 1778, Philadelphia proved to be not quite far enough way for Alexander, and he went aboard ship with the British Royal Navy finally making his way to London by at least 1782. He died there in November 1805.

Even if Alexander had decided to “turn coat” again back to the patriots’ side, he would have had nothing to return home to. By 1780, the State of Maryland judged him guilty of high treason and seized most of his property, which was turned over to the Town of Elkton. His wife, who remained a true blue patriot in Maryland, was allowed to keep the main house that her husband’s father had built in 1735, which still stands at 323 Hermitage Drive in Elkton, where it is known as “The Hermitage.”


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