This week would’ve marked the 167th anniversary of the Upperville Colt & Horse Show, and in celebration of this historic event, we’re taking a closer look at a classic photograph from the show.

Gene Pillion may be 88, but he remembers showing at the Upperville Colt & Horse Show in Upperville, Virginia, as if it was last summer, rather than five decades ago.

Pillion rode for National Show Hunter Hall of Fame owner Theodora Randolph—better known as Mrs. A.C. Randolph—from 1956-1964 when he was in his late 20s and early 30s.

He said Upperville was always the highlight of the show season. “Back then we only had one ring and the outside course,” said Pillion.

“The appointments class and the stake class was over the outside course,” he continued. “All the open classes were more or less just in the ring, over a figure-eight course, around the outside, across the center and across the grandstand. There was one jumper class, used to have it on Sunday, called it the high jump, in front of the grandstand. They always had big fences. On the outside course there was a big stone wall and a 36’ in-and-out. It was a lot of fun there.”

Gene Pillion rode Nereus over the outside course at the Upperville Colt & Horse Show (Va.) in 1961. Allen Photo

Randolph bred Thoroughbreds, some of which she showed on the line at Upperville.

“She bred them all to be race horses, and if they didn’t have enough speed or didn’t show potential, they came back home, and we made hunters out of them,” said Pillion. “They were converted to whatever it was going to be.”

Pillion, who also did a stint riding for Sallie Sexton, and another man would re-start the race horses as hunters, and if and when they were ready, Pillion would take them to a small show. This photo from 1961 is of Pillion on Nereus, a top performer in the hunter divisions, over Upperville’s outside course. Pillion assumes from his hunting whip and attire it was an appointments class.

“Nereus came along and showed in the green working, and the reason he showed in green working [rather than the conformation] was his ankles had been pin fired,” Pillion recalled. “I showed him in the green working as a green horse and then continued on with him over 4’.”

Pillion competed against the likes of Cappy Smith, Bobby Burke, Robert Kerns and Jack Payne.

In addition to Nereus, Pillion showed horses like Quiet Flite, Momery and Black Adam for Randolph. During the winter, he whipped in for Piedmont Fox Hounds (Virginia) under huntsman Albert Poe. At the time, Randolph was joint-master alongside Paul Mellon.

Eventually, Pillion made his way to Ohio where he worked for a family. Now retired, he visited Upperville recently to see how different it is today with multiple rings with manicured footing going on both sides of the street and a full slate of jumper classes.

But some things that were true then still are.

“For Upperville it always rained,” he recalled.

If you enjoyed this story and are interested in learning more about Upperville, check out “Showing Beneath The Oaks Since 1853,” an article in the June 1 & 8, 2020 issue that chronicles the history of this show.

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