Known by his middle name, Wyndham, in 1872 Walden and his wife Caroline moved from New York to Middleburg in Carroll County, Maryland where they established "Bowling Brook Farm" to breed and train thoroughbred race horses.
Wyndham Walden trained his first Preakness Stakes winner in 1875 then two years later began a streak of five straight victories, all of which came with horses owned by George L. Lorillard. Walden won the Preakness for a seventh time in 1888 with his own horse, Refund. The win set a record for a trainer which still stands. During a career spanning thirty-one years between 1872 and 1902, he also won the Belmont Stakes four times and trained more than 100 Stakes race winners.
On Wyndham Walden's passing in 1905, Bowling Brook Farm was taken over by his wife then on her passing by his son Robert who lived there until his death in 1951. Over the Walden family's eighty year history in racing they raised and trained winners of more than one thousand races.
Robert Wyndham Walden was inducted in the National Museum of Racing and Hall of Fame in 1970.