Henry Augustine Tayloe (April 8, 1808 – July 15, 1903) of Oakley Plantation, Essex County, Virginia, later Gallion, Canebrake, Alabama, was an American planter, slaveholder, horse breeder and racer, and land speculator in the 19th century.

A younger son of John Tayloe III of The Octagon House and Mount Airy, a wealthy planter in Washington, D.C., Virginia, and Maryland; after living in Maryland for a time after graduating from UVA the young Tayloe went to Alabama in 1834, where he was among the pioneers in developing slave labor cotton plantations in the Canebrake region.

He also acted as a land agent, acquiring numerous plantations in the area for investment by his four older brothers, who were also extremely wealthy.

A committed breeder and racer of horses, in 1838 he founded the Fair Grounds Race Course near New Orleans with Bernard de Marigny.

[3] As a youth, Tayloe asked John C. Calhoun, then Secretary of War, to support him for an appointment to West Point.

Noting Tayloe was the son of a rich man, Calhoun advised him to leave such an appointment open to a boy who needed government aid in his education.

Tayloe transported many enslaved African-American workers from his family's Virginia and Maryland plantations to Alabama.

As the Deep South was developed for plantations, an estimated total of one million enslaved persons were forcibly transported there, breaking up numerous families.

At Walnut Grove Tayloe built a frame residence of eight rooms, one of the first large homes in the area.

He entered his horses in races at the Greensboro track, Livingston, Mobile and Montgomery, Alabama; Columbus, Georgia; and New Orleans, Louisiana.

His brother William Henry Tayloe, heir to Mount Airy in Virginia, sent fourteen racehorses to him at one consignment.

Black Maria won the deciding fourth heat, the same afternoon, thus having run a total of 16 miles.

[11] On the third day, Henry's Pizarro raced against: John P. White's Collier, Thomas Doswell's Lady Pest, and James Harrison's Goliath[11] Finally Tayloe advertised in the Constitutional Whig December 14, 1832: Timoleon (horse), by Sir Archy, "will stand the ensuing season at my stables near Lloyd's, Essex County, Virginia, from his plantation Oakley, King George County(should read Essex, County), Virginia.Tayloe began the year subscribing to a Sweepstakes Race at The Central Race Course in Baltimore, Maryland, against: John M. Botts, Edward Parker, William R. Johnson, William Wynn, R.F.

In April he advertised in The Evening Post stud services for Autocrat, "bred by Edward Smith-Stanley, 14th Earl of Derby, and imported into New York in 1831 by William Jackson.

Bott's Gohanna colt, James M. Selden's Unnamed, William Wynn's full brother to Anvil, R.F.

On April 10, 1838, the first race for "The Creole Purse" of $1,000, (~$28,613 in 2023) free only for horses bred and owned in the state of Louisiana.

Fourth Day-"Jockey Club Plate" value $1,500 and $500, -four mile heats-to the winner, and $500 to the second best horse, provided more than two start.