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CSS Jamestown, a 1300-ton side-wheel gunboat, was built in at New York City in 1853 as a civilian steamer of the same name. She was seized by the State of Virginia in April 1861 for use by its navy. Later turned over to the Confederate Government, she was formally renamed Thomas Jefferson but continued to be generally known as Jamestown. During the rest of 1861 and into 1862, the ship was part of the James River Squadron. She took part in the the battle of 8 March 1862, in which CSS Virginia destroyed USS Cumberland and USS Congress, and in the 9 March 1862 action between Virginia and USS Monitor. When Virginia sortied again on 11 April 1862, Jamestown steamed over to the north side of Hampton Roads and captured three Union merchant ships.

As the Confederate position at Norfolk became tenuous in late April and early May, Jamestown helped evacuate casualties and supplies from there to safer areas on the James River. On 15 May 1862, as Federal warships assaulted the defending fortifications at Drewry's Bluff, CSS Jamestown was sunk nearby to block the channel leading up the James to Richmond. Her wreck remained in that location for the rest of the Civil War

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