It is run over four and a half miles, almost two miles further than any conventional flat race. The course includes grass verges, road crossings and a humpback bridge. Anyone, with any horse, can turn up and compete - children on ponies often take on farmers with thoroughbreds. The runner-up usually receives more prize money than the winner. And there is no betting.
There are no accurate records, but anecdotal evidence suggests that races have been staged at Kiplingcotes since the early 16th century, while the first Derby was run there about 100 years later. For all its quirks, the Kiplingcotes Derby is approaching its 400th birthday when the Grand National is barely 150. The other Derby, at Epsom, was run for the first time in 1779.
The Gold Cup, like the Kiplingcotes Derby run by tradition on the third Thursday in March, has succumbed to the weather several times in its paltry 70-year history, but at least one rider has completed the Kiplingcotes course each year for generations, and with good reason. 'If there was ever a break, we'd lose the right to gallop through some of the land,' Ken Holmes, who has ridden six of the last 10 winners of the race, says. 'The only time there looked like being a break was in 1947, when there were mountains of snow. But a farmer led a carthorse around the course to keep it going.'
Holmes's success 12 months ago, on the thoroughbred Tulum, equalled a 150-year-old record for the number of wins in the race by one rider. Six victories in the Epsom Derby would make a jockey a multi-millionaire, but Holmes knows that the Kiplingcotes offers a less tangible reward. 'It's just prestige,' he says, 'there's nothing in it money-wise.'
Certainly not for the winner, anyway, given the Kiplingcotes Derby's bizarre system of reward. 'Around half a dozen of the nobility around here originally put in the money to set up the race,' Alison Hawkins, an expert on the contest's history, explains. 'Years ago that money was invested, with the three per cent annual interest being used to provide the first prize. The horse which came in second won the entrance fee of all the others, so the runner-up often got more than the winner.'
To enter the Kiplingcotes Derby, you and your horse need only arrive at the weigh-in before 11am on Thursday morning. 'Anyone can turn up,' Holmes says. 'You could turn up with Shergar.' After weighing in, the field walks to the start, taking about half an hour, and the race begins. 'The first mile and three quarters is on grass verges beside a country road,' Holmes says. 'It's real good turf, as good as any racecourse, with enough room to get seven or eight upsides.
'After that it gets really hazardous. You've got to get up on a verge where there's only space to go in single file, and if you can't get on it you're going down towards a railway bridge on a hard road. That's when the sparks fly.'
It is, as Hawkins admits, 'basically a free-for-all, everyone goes for it'. None more so than Holmes. His riding days are drawing to a close - though he refuses to disclose his age, he admits that he is a grandfather - but one ambition remains. 'I'm trying to break the record, and then I might try for one more to give someone something to try for in the future.'
Were a bookmaker present - none has been since the early 1950s - Holmes and Tulum would probably be hot favourites for Thursday's race, though as the jockey points out, 'you can't bet on it because you never know what might turn up'.
For the record, Shergar is a bay with a white blaze and four white feet.
The Kiplingcotes Derby will be run Thur 17 Mar, weigh-in at 11am, near Market Weighton, Yorkshire. Leave Market Weighton on the A163 towards Middleton- on-the-Wold, the racecourse crosses the road
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