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Monticello High School, also called Jefferson County High School, is a National Historic Landmark (listed in 1999). Originally built in 1852 by slave labor from Samuel Carroll?s plantation with bricks furnished by George Taylor, it was first known as Jefferson Academy. The first brick school building in the state, the school was expanded (with added columns) in 1915. It is located at 425 East Washington Street.

The monument reads: "Jefferson County High School, erected 1852. Charter Granted 1832 by Legislative Council. First Brick School Building in State. Bricks made by George Taylor Plantation. Building constructed by Samuel Carroll with slave labor. This memorial presented by senior class 1955."