Since 2021, the Randolph Perpetual Trophy has been presented by the Bonnie family in memory of their matriarch, Mrs. Theodora Ayer Randolph. The award recognizes an individual who embodies Mrs. Randolph’s philosophy: a deep respect for equestrian sport, an appreciation for well-turned-out horses, and a passion for sharing her interests with others—no matter their heritage or means.
This year, the Upperville Colt & Horse Show and Bonnie family are proud to honor Mike and Wendy Smith with this award. Their longstanding commitment, generosity, and vision have made a lasting impact on the Upperville community.
For Mike Smith, the recognition represents the full circle of a lifelong passion. A Winchester native, he first attended the Upperville show as a boy, dreaming of one day competing there himself. “I loved the show,” Smith recalled. “It was at Upperville that I realized how I needed to ride—and how the horses needed to go—to be competitive at that level.”
As a teenager, he trained with Katie Monahan Prudent, competing in both the hunter and jumper divisions. In a fitting twist of history, his junior hunter, East Avenue, was bred by Theodora Ayer Randolph, herself. Prudent also piloted East Avenue to memorable wins in the Working Hunter division.
After selling his family business in 2022, Smith “returned 100%” to the sport. Today, he competes in the Masters and Amateur show jumping divisions and owns several top-tier horses ridden by local professional Thaisa Erwin and Olympic champion McLain Ward. Though he retired from foxhunting a few years ago, Smith remains deeply involved with the Piedmont Foxhounds, where he serves as Executive Director.
Smith’s leadership has also left a positive mark on the Upperville show. As board president from 2014 to 2018, he introduced all-weather footing, improved the VIP experience, and elevated the competition by reintroducing FEI classes and a CSI4* Grand Prix. His goal, he explained, was “to bring top riders back who had given up on Upperville.” Today, as a Director Emeritus, he continues to support the event, including sponsorship of this year’s $62,500 FEI CSI4* Welcome Stakes.
While Mike’s devotion centers on horses, Wendy Smith shares his love for the land that sustains them. Together, the couple has purchased several large farms in the area and placed them in conservation easements to protect the countryside from development. “Conservation is important for foxhunting and horses in general,” Smith explained. He also ties the practice to his involvement in steeplechase racing, noting that foxhunting is key to keeping racehorses fit between seasons. “We have a responsibility to be stewards of the land and pass it on to future generations. Working on farms and learning responsibility for animals is what life is really about.”
Reflecting on the honor of receiving the Randolph Trophy, Smith emphasized the personal significance of the award. “Shelby [Bonnie] and I have been friends since our teens,” he said. “It is a real honor that they gave this award to us.”
By their generosity, vision, and stewardship, Mike and Wendy Smith have not only helped shape the future of the Upperville Colt & Horse Show but also ensured that the values Mrs. Randolph cherished will carry on for generations.
Photo Courtesy of Anne Gittins