In 1798 a mile track was laid out which extended from the rear of what is now the site of Decatur House at H Street and Jackson Place, crossing Seventeenth Street and Pennsylvania Avenue to Twentieth Street.
The inaugural match featured John Tayloe III's Lamplighter and Gen. Charles Carnan Ridgely's Cincinnatus, for 500 guineas, ran in 4-mile heats, and won by the former, a son of Imp English bred stallion Medley.
The only initial building was a small elevated platform for the judges.
The "carriage folk" took to the infield for views of the contests and the strandees crested the outside of the course.
The site of today's Eisenhower Executive Office Building, this first course's history was short lived as it stood in the path of L'Enfant's city plan.

In 1802 the Club sought a new sight for the tract, as the current one that lay the rear of what is now the site of Decatur House at H Street and Jackson Place, crossing Seventeenth Street and Pennsylvania Avenue to Twentieth Street-today the Eisenhower Executive Office Building-was being overtaken be the growth of the Federal City.
With the leadership of John Tayloe III and Charles Carnan Ridgely and support of Gen. John Peter Van Ness, Dr. William Thornton, G.W. P. Custis, John D. Threlkeld of Georgetown and George Calvert of Riversdale, Bladensburg, Maryland, the contests were moved to Meridian Hill, south of Columbia Road between Fourteenth and Sixteenth Streets, and were conducted at the Holmstead Farm's one mile oval track.

Tayloe's interests included American horse racing, being a leader in this sport during the period of 1791–1806.
His son, Henry Augustine Tayloe, founded the Fair Grounds Race Course in New Orleans with Bernard de Marigny in 1838.
Like his father, John Tayloe III was a successful horseman, and owned such celebrated racehorses as Belair, Grey Diomed (who he imported, and for him sired Sir Archy whose progeny include Boston (horse), Timoleon (horse), Lexington, Secretariat and American Pharoah), and others.
In 1798 a mile track was laid out which extended from the rear of what is now the site of Decatur House at H Street and Jackson Place, crossing Seventeenth Street and Pennsylvania Avenue to Twentieth Street. The inaugural match featured John Tayloe III's Lamplighter and Gen. Charles Carnan Ridgely's Cincinnatus, for 500 guineas, ran in 4-mile heats, and won by the former, a son of Imp English bred stallion Medley. The only initial building was a small elevated platform for the judges. The "carriage folk" took to the infield for views of the contests and the strandees crested the outside of the course. The site of today's Eisenhower Executive Office Building, this first course's history was short lived as it stood in the path of L'Enfant's city plan.
In 1802 the Club sought a new sight for the tract, as the current one that lay the rear of what is now the site of Decatur House at H Street and Jackson Place, crossing Seventeenth Street and Pennsylvania Avenue to Twentieth Street-today the Eisenhower Executive Office Building-was being overtaken be the growth of the Federal City. With the leadership of John Tayloe III and Charles Carnan Ridgely and support of Gen. John Peter Van Ness, Dr. William Thornton, G.W. P. Custis, John D. Threlkeld of Georgetown and George Calvert of Riversdale, Bladensburg, Maryland, the contests were moved to Meridian Hill, south of Columbia Road between Fourteenth and Sixteenth Streets, and were conducted at the Holmstead Farm's one mile oval track.
Tayloe's interests included American horse racing, being a leader in this sport during the period of 1791–1806. His son, Henry Augustine Tayloe, founded the Fair Grounds Race Course in New Orleans with Bernard de Marigny in 1838. Like his father, John Tayloe III was a successful horseman, and owned such celebrated racehorses as Belair, Grey Diomed (who he imported, and for him sired Sir Archy whose progeny include Boston (horse), Timoleon (horse), Lexington, Secretariat and American Pharoah), and others.
John Tayloe III