He attended the private schools of Charleston and went on to graduate from Washington and Lee University in Lexington, Virginia, in 1885.

Residing in Walterboro, Heyward resumed the growing of rice on the part of the plantation he inherited from his parents.

He became a member of the Knights of Pythias and served as a captain of a cavalry company in Colleton County.

[1] Announcing his candidacy in 1901 for the gubernatorial election of 1902, Heyward emerged as a frontrunner despite being a novice to politics.

"[3] After leaving office, Heyward was appointed by President Woodrow Wilson in 1913 to be the Collector of Federal Internal Revenue Taxes for South Carolina.