April 2026 Issue

April 2026 | EAST COAST EQUESTRIAN 28 Of Timber & Trees The Maryland Hunt Cup as Family Business Bosley “Growing up I thought the Hunt Cup was the greatest race in the world,” said Betty (née Bosley) Bird in 1954 after Marchized won. More than two decades later she was still saying it. “It still is.” The Bosleys had pursued the Cup for years. Patriarch John Bosley Jr. rode in thirteen Hunt Cups between 1911 and 1926, coming closest in 1919, when Black Amber finished second to Chuckatuck, ridden by Jervis Spencer Jr. Betty herself was a gifted horsewoman, a show rider with a talent for teaching horses tricks. Her gray Count Stefan had once been considered dangerously vicious and was purchased by her father for $85. “By the time the war was ending he was a different creature,” she recalled. Her father even appealed to the Hunt Cup committee to let her ride him. “Not that Daddy approved of girls riding races but there weren’t any other riders available that he wanted.” The committee said no. The mount went in- stead to her brother, John “Jackie” Bosley III, who finished behind the mighty Winton. Betty later laughed at the irony. “I was very disappointed that I didn’t ride, but when women were finally allowed in the race, I didn’t approve at first either!” The Bosley line continues into the present through Advanced three-day event rider Isabelle Bosley, this month’s cover subject—another branch of the same Maryland hunt-country tree. Isabelle grewup foxhunting, galloping racehorses, and riding timber, which is to say she grew up in the same soil that has long produced Hunt Cup riders, steeplechasers, and eventers alike. Davies “Winning the Hunt Cup is something you dream about your whole life,” Teddy Davies said after his ride in 2022, when at just 18 years old he captured the Cup and set a new course record. Few modern families illustrate the Hunt Cup’s living family tree more clearly than the Davies– Miller household, where steeplechasing runs through multiple generations. Teddy’s father, Joe Davies, won the Maryland Hunt Cup three times as a rider—1998 on Florida Law, 2000 on Swayo, and 2005 on Private Attack. He later added another chapter as a trainer, preparing winners including Senior Senator, who captured the race three times (2016, 2018, 2019), as well as Teddy’s 2022 champion Vintage Vinnie. From the fami- ly’s Dunmore Farm in Monkton, at the center of Elkridge-Harford hunt country, the Davies stable has bred, produced, and campaignedmany of the timber horses that define the modern Maryland circuit. The other side of Teddy’s pedigree carries an equally deep timber lineage. His mother, Blythe (Miller) Davies, won the 2011 Maryland Hunt Cup and earlier led the National Steeplechase Association rider standings in 1994 and 1995. Her father, Bruce Miller, was one of the sport’s most respected horse- men, a leading trainer whose horses included Make Me A Champ, winner of the 2005 Hunt Cup. Blythe herself rode the Hall-of-Fame steeplechaser Lonesome Glory during his championship career. The Miller family’s Pennsyl- vania timber roots have long intertwined with Maryland’s hunt-country circuit—and with other Hunt Cup dynasties, in- cluding the Fenwicks—another example of the Pennsylvania– Maryland alliances that have long knit the sport’s community together. Fenwick “The race has always been bigger than life,” Charlie Fenwick Jr. told The Maryland Horse in 1990. “Steeplechasing has given us a tremendous amount of excitement and satisfaction, and it is our hope that we can return some of that to the sport through our children.” If any family has come to embody the Hunt Cup itself, it may be the Fenwicks. Charlie’s father, Cuppy Fenwick, served as Hunt Cup secretary for thirty years. Charlie’s mother, Ann (née Stewart) Fenwick, extended the family’s roots even deeper. She descended fromRedmond Stewart Sr., who placed in the inaugural Hunt Cup, and fromRedmond ConynghamStewart Jr., who won the race in 1904 aboard Landslide. She was also the great-granddaughter of G. Bernard Fenwick, who helped design the 1922 course. Ann herself became a three-time Hunt Cup-winning trainer, including with Ivory Poacher in 1993. Charlie Fenwick’s great equine partner was Ben Nevis. Early attempts to hunt the horse convinced Charlie’s brother Bruce that the enterprise might be doomed. “It was a rodeo,” Bruce said. “He lunged and bolted through the woods. We didn’t get anywhere.” Charlie persisted anyway. “He always pulled like hell,” Fenwick later said. “After fifteenminutes my arms would be screaming.” Ben Nevis broke his maiden in 1976 and won eight races the next year before taking the 1977 Hunt Cup. “Ben Nevis erupted at the drop of the flag,” wrote Peter Winants. Fenwick stood straight up in his irons trying to steady him, but moderation was never Ben Nevis’s gift. Once his rider let him run, the pair flew the fences and led throughout. The wider Fenwick branch includes Charlie’s uncle H. Robertson Fenwick—Master of Fox- hounds of the Green Spring Valley Hounds, rider of the dual champions Fluctuate (1959–60), trainer of the 1956 winner Lancrel, and trainer of Jay Trump, the first American-owned, bred, and ridden horse to win the Grand National at Aintree in 1965. InMaryland timber racing, strong roots spread quietly. Sometimes through bloodlines. Some- times through horses. Often through both. Fisher “Blockade wanted to be ahead of the master, hounds and fox—and liked to kick hounds,” wrote historian John E. Rossell Jr. “So what could be done with a big, strong chestnut that was a three- time dropout?” Janon Fisher Jr. answered that question in style. In 1938, he paired the unruly son of Man o’ War with jockey J. Fred Colwill, and the result was an 8:44 course-record victory. The next year Fisher gave Colwill a simple instruction: “Stay in front. Don’t let any horse in front of you.” Blockade obliged. In 1940, he completed the Hunt Cup’s first three-peat. Fisher’s influence did not stop with one horse. A breeder as well as a trainer, he later produced Mountain Dew, another timber legend. “He was all Fisher—born, bred, owned, trained and ridden by the family,” Winants wrote.The elegant gelding started eight Hunt Cups, winning three, finishing second three times, and third once. In 1968, one fence from home, he bowed a tendon and retired to become a favored Green Spring foxhunter. “Janon Fisher was a Master of Masters,” Winants wrote. “He knew hounds, horses, coun- try, and people like a book.” Hannum “From the time the race opened to out-of-staters in 1909,” noted John E. Rossell Jr. inTheMaryland Continued from page 4 With permission from the Alex Brown archives, all rights reserved.