Planter
Thomas Sim Lee's became a planter in Frederick County, Maryland, some time between 1775 and 1790. In 1775, Thomas Sim Lee was a resident of Prince George's County, and not in the Frederick County, Maryland census until 1790. Complicating matters, in the 1798 census his home was in Montgomery County, and in 1802 in the new District of Columbia, specifically in the Georgetown section in 1804-1807. After retiring from political life in 1794, Governor Lee focused his attention on his estate, Needwood, in Frederick County, Maryland. He bought some property in Frederick County in 1775 and an interest in Needwood from pioneer educator Rev. Bartholomew Booth in 1783, but the transaction took decades, possibly because Booth's son and executor sold the land to one of two wealthy women who had emigrated to the colonies with pioneer educator Rev. Bartholomew Booth, Mary Valiens, who married Gen Horatio Gates and whose interest was relinquished in 1816. (Her sister Anna Bardsley purchased land in Washington County, Maryland). In the first federal census, in 1790, Lee owned 119 enslaved people in Frederick County. In the same year, Lee also owned 16 slaves in Montgomery County, Maryland, which included Georgetown before creation of the federal city, as discussed below. In 1800, Lee owned 109 slaves in Frederick County, and 13 in Georgetown in the newly established District of Columbia. Lee sold four slaves to his daughter Elizabeth Digges Lee in 1806, who were manumitted in 1812, about seven months after her marriage to Outerbridge Horsey, a federalist from Delaware who served in the U.S. Senate, then spent his final years near Needwood. His grandson (also Thomas Sim Lee), continued to operate Needwood using slave labor, but paid taxes only for 13 slaves in 1850.
This Thomas Sim Lee also maintained a winter home in Georgetown, near the nation's capital. Federalists frequented the home.
Thomas Sim Lee was on the Board of directors of the Patowmack Canal, which George Washington and other members intended to connect the Tidewater near Georgetown with Cumberland. The project, which started in 1785, was completed in 1802, but closed in 1828. Nonetheless, sections were deepened and incorporated into the Chesapeake and Ohio Canal, now a national park.