It reputedly began in 1519 and takes place on the third Thursday in March, often in exceptionally adverse weather conditions.

[1] One quirk of the ancient rules means that the second place rider often receives more in prize money than the winner.

The race starts near the former Kiplingcotes railway station and runs for 4.5 miles (7.2 km), finishing at Londesborough Wold Farm.

The race was started by the Earl of Burlington in 1519,[5] and the first prize is the accrued interest of an original investment of 16 guineas by the organisers, who stipulated the rules as laid down in 1618; A horse race to be observed and ridd yearly on the third Thursday in March open to horses of all ages to carry horseman's weight, 10 stones, exclusive of saddle, to enter at ye post before eleven o'clock on the morning of ye race.

If such a thing happened, the youth would put in his entry on some old dobbin released from plough[ing] a field...."[9] During the harsh winter of 1947, no one was daring enough to take part, and so one local farmer took it upon himself to lead a lone horse around the course, ensuring that the historic race would survive.