Dryden District School No. 5, also known as Eight Square Schoolhouse, is a historic octagonal school building located in Dryden in Tompkins County, New York. It was built in 1827 and is a simple one-room, one-story, brick octagon style building constructed with a low pitch hipped roof banded by a plain narrow frieze. A circular brick chimney rises from the center of the standing seam metal roof. Also on the property are two free standing, wood frame, gable roofed outhouses. It was used as a school until 1941 and is now a facility of the Dewitt Historical Society. It was listed on the National Register of Historic Places in 1994.