Richard Cheshire was born in Bladen County, North Carolina on March 27, 1759. In 1779 he volunteered as a private in the Bladen County Regiment of the North Carolina Militia, where he served under Colonel Thomas Brown. He later served as a private in a Bladen County Light Horse unit. In 1839 he made a sworn affidavit in support of Lucy Brown's application for a widow's pension. He died in Bladen County on January 26, 1851.