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Returning to Sidesaddle in Kennett Square


SIDE SADDLE RACEMore than most sports, riding to the hounds is all about tradition, speaking of a time of vast estates, gamekeepers, manor houses and wearing the proper attire. So, should anyone be surprised that some ladies of the hunt are now riding sidesaddle while tearing across the countryside after the fox—a form that was routine for their great-grandmothers but later rejected by their grandmothers?

On March 27, almost a dozen women will dress in long skirts and accouterments to gallop across the countryside at Plantation Field near Kennett Square in the Mrs. Miles B. Valentine Memorial Side Saddle Race, a first-of-this-century event.

“There is a bit of resurgence in riding aside instead of astride,” says Kirstie Grabosky, co-chair of Mr. Stewart’s Cheshire Foxhounds’ Point-to-Point Races, who has been practicing riding sidesaddle for the past few years.

Riding sidesaddle, common until about a century ago, was predicated on various feminine physiology myths and the reluctance of males to recognize that their wives and daughters could ride tall in the saddle as fast and as well as they could. Gradually, sidesaddle riding was abandoned. But today, with the ability of women no longer challenged, some see fun and charm in returning—at least, part of the time—to the past.

“Our inspiration has been the women of Ireland, the Dianas of the Chase,” Grabosky says. 

The Side Saddle Association of Ireland was officially formed in 1981, and the women have been racing and jumping ever since. Sidesaddle races have also started up recently in Virginia’s hunt country.


In riding sidesaddle, a woman usually sits on the left side of the horse with her left foot extended into a single stirrup and her right leg folded somewhat into the saddle and the side of the horse. The saddle has two pommels, a fixed head and a flexible racing head, for more stable riding. “People seem to think that sidesaddle riding is more precarious,” Grabosky says. “But I haven’t found that to be the case.” 

Grabosky also says that, while a horse may need some adjustment to its rider not being astride, it’s not a difficult transition. “Our women needed no convincing at all,” when they were approached about a sidesaddle race, she says. 

The sport is not inexpensive. However, Grabosky points out that a custom English-made saddle costs between $2,000 and $4,000, not to mention the new wardrobe with flowing skirts. Riders vary in age from 15 to 55, although teenage girls will not ride in competition.

“We’re anxious to give it a try,” Grabosky says optimistically. “We’ll see where it goes.”