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One of the oldest communities on the East Coast, Port Tobacco first existed as the Native American settlement of Potopaco and was colonized by the English as early as 1634. Port Tobacco became a major seaport during the late 1600s and was the original Charles County government seat. In addition to being a hot spot for confederate conspiracy and a part of John Wilkes Booth’s escape route, Port Tobacco suffered from local conflict as well. A vote was taken to move the county seat to La Plata where the railroad industry was becoming more resourceful than the seaport of Port Tobacco, but the vote did not pass. Then in 1892, the center part of the courthouse was burned in a mysterious fire and the county seat was moved to La Plata.

Sites to visit include the reconstructed Port Tobacco Courthouse that is furnished as a 19th century courtroom and has exhibits on tobacco and archeological finds located upstairs; Catslide House, one of the four surviving 18th century homes in the area; the restored One-Room Schoolhouse built in 1876 and used until 1953; Chandler's Hope, the first Charles County settlement and where the Carmelites first took residence in America; and Thomas Stone National Historic Site, the plantation home of one of the four signers of the Declaration of Independence.

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