The origins of the Middleburg Hunt can be traced to the great international foxhunting match between A. Henry Higginson's Middlesex and Harry Worcester Smith's Grafton hounds in 1905. 

The match was arranged to settle a dispute between the gentlemen concerning the superiority of their respective English and American packs of hounds. Mr. Smith's American hounds decisively won the match. 

The hunting during those two weeks of the match as well as the consequent newspaper publicity established Middleburg as the axis of the Hunt Country of America, since the hunting took place largely in the area near the village.