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Women’s Sidesaddle Racing is an Intriguing Return to Tradition

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More than most sports, riding to the hounds is all about tradition, bespeaking a time of vast estates, gamekeepers, manor houses and 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? 

“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 riding sidesaddle for the past few years. 

Riding sidesaddle, common until about a century ago, was predicated on various myths about female physiology and the reluctance of men to recognize that their wives and daughters could ride tall in the saddle as fast and as well as they could. Sidesaddle riding was eventually abandoned so that today, 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 recently in Virginia’s hunt country.

In riding sidesaddle, a woman usually sits on the left side of the horse, her left foot in the stirrup and her right leg folded somewhat into the saddle and side of the horse. The saddle has two pommels, a fixed head and a flexible racing head, for more stable riding. 

The sport is not inexpensive. Grabosky points out that a custom English-made saddle costs between $2,000 and $4,000, not to mention a new wardrobe with flowing skirts. 

“People seem to think that sidesaddle riding is more precarious,” says Grabosky. “But I haven’t found that to be the case.” 

The Willowdale Steeplechase hosts the Side Saddle Race at 1 p.m. on May 14. 

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