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History of Steeplechase Racing


The first steeplechase took place in 1752 in County Cork, Ireland, a 4.5-mile match race across the countryside. Soon, the sport was off to the races, with crowds turning out to cheer thoroughbreds galloping over natural terrain and leaping over fences, walls and hedges. 

John Hislop, an English horseman and author, wrote: “Steeplechasing has about it rather more glamour and excitement than the flat, a trace of chivalry, a spice of danger, and a refreshing vigor that the smooth urbanity of flat racing lacks. The atmosphere is less restrained, more friendly, more intimate.”  

In the United States, the sport dates back to 1860, embraced by the foxhunting set on Philadelphia’s Main Line. Soon, races were up and running in Delaware, Maryland and Virginia.

Jonathan Sheppard of Unionville is the leading U.S. steeplechase trainer of all time in victories and earnings. He started his illustrious career as a jockey more than half a century ago, coming over from his native England to try his luck on the American stage. “Radnor Hunt goes back a long way for me because I rode in some races there as a jockey in the early 1960s,” says Sheppard, now 76 and currently training 60 thoroughbreds, including 20 steeplechase mounts. 



He notes that each course has its own personality. Winterthur is a good match for horses that take to timbers, or jumps over wooden-rail fences. Willowdale has its celebrated water jump.

A few years ago, Radnor changed from a traditional left-handed course to a right-handed course, which created a longer homestretch. “That makes it special, gives it more character,” Sheppard says. “It’s a little different from some courses because it’s quite hilly. You have to use strategy to save your horse’s energy, but you don’t want to lose position. It takes a horse who’s used to rolling ground to succeed there.”

Sheppard often attends meets at Radnor, Willowdale and Winterthur, events steeped in the excitement of a time-honored sport. “The thrills and spills of steeplechasing are captivating—the thundering hoof beats, the horses jumping and racing over streams,” he says.

Sheppard is the only trainer to take the American steeplechase Triple Crown, doing it with Flatterer, the sole horse to win the Eclipse Award for Outstanding Steeplechase four years in a row. He also is the only trainer to serve as president of the National Steeplechase Association.

Sheppard co-owned Flatterer with Bill Pape and George Harris. The bay gelding was so good that handicappers saddled him with 176 pounds at Radnor in 1986, the highest weight ever assigned in a steeplechase. Flatterer won going away by four-and-a-half lengths.

Like all steeplechasers, Flatterer started his career in flat racing. He won a few races but was mostly a middling performer. So Sheppard tried him on jumps, where Flatterer ultimately became the top earner in U.S. steeplechasing, also winning prestigious races in Britain and France.

Radnor Hunt in the 1920s.

Radnor Hunt in the 1920s.

“Good jumpers have stamina and athleticism,” says Sheppard. “What they lose in speed, they make up in endurance. There are horses who are succeeding at 10 and 12 years old.”

After he retired from steeplechasing, Flatterer took on a third career, excelling at dressage. He died in 2014 at the age of 36. “He was a great horse with a great heart,” Sheppard says.

Steeplechase aficionados reserve weekends in May for the three big meets. This year, however, the calendar is a bit different. Though Willowdale fans have come to know their meet as a Mother’s Day tradition, the 2016 Point-to-Point will run on Mother’s Day (May 8) instead, with Willowdale coming the following Sunday (May 15).

Why the change? It has to do with the leap year and the National Steeplechase Association schedule. The last time this occurred was in 2011.

Nonetheless, both race directors view the change as positive.

“A few years ago, Winterthur Point-to-Point restructured the event to make it more convenient, family friendly and enjoyable,” says Jill Abbott. “We’ll offer a wonderful day to spend with family and friends, and we’re going to make it easy and a fun day to treat moms.” 

Willowdale’s Leslie White says the later date is an opportunity to attract new fans who might not have been

Willowdale founder Dixon Stroud in his racing days

Willowdale founder Dixon
Stroud in his racing days

able to attend previously due to family obligations on the holiday. “While Willowdale is known as a Mother’s Day tradition, fans won’t miss a thing,” she says. “They will still enjoy their much-loved community event, exciting racing, and fun activities, all while having a day in the country.”

Next year, Winterthur will revert back to the first Sunday in May. Willowdale, meanwhile, will celebrate its 25th-anniversary running on Mother’s Day.

Dixon Stroud, Willowdale’s founder and race chairman, earned his reputation in the saddle, competing from the 1960s to the early 1990s. He rode at Winterthur and Radnor, as well as steeplechase races at Delaware Park. He started playing polo in 1971. In 1984, he rode Bewley’s Hill to victory in the Maryland Hunt Cup. “Confirmation, breeding and training are what make a good jumper,” he says. “Also, what’s under the bonnet, as the British say. Some horses are competitive by nature.”

In 1993, when Willowdale debuted, Stroud envisioned “a new venture and new jumps.” But the meets are not solely for the horsey set. “Think of many people, all dressed up and eating and drinking and talking at a big party,” he says. “It’s a spectacle, getting close to the fences and seeing the jumping. If you just have racing people, it doesn’t work.”