At age two, Pleasant Colony won two of his five starts including the Remsen Stakes. At age three, in the spring of 1981 he was second in the Fountain of Youth Stakes. Pleasant Colony lost 3 of 4 races to Akureyri. He lost the Fountain of Youth Stakes and the Pilgrim Stakes besides finishing behind Akureyri in the Florida Derby. He also was defeated by Akureyri in the Remsen Stakes but was placed first through disqualification. After Pleasant Colony's fifth-place finish in March's Florida Derby, his owner dismissed his trainer and replaced him with John P. Campo. Ridden by jockeyJeffrey Fell, Pleasant Colony then won April's Wood Memorial Stakes by three lengths.
In the 1981 Kentucky Derby under regular jockey Jorge Velasquez, Pleasant Colony held off a powerful stretch drive by Woodchopper to win by three-quarters of a length. The expected rivalry with Woodchopper never materialized in the Preakness Stakes. Pleasant Colony came from behind to win by a length over Arkansas Derby winner Bold Ego with Woodchopper far back in eleventh place. In the third and final leg of the Triple Crown series, the Belmont Stakes, Pleasant Colony finished third to winner Summing.
From 1982 to 1998, Pleasant Colony stood at Thomas Mellon Evans's historic Buckland Farm in Warrenton, Virginia. He became a very significant sire, producing seventy-three stakes race winners including more than a dozen Grade I winners and the following champions:
Pleasant Colony's daughters have produced a number of Grade 1 stakes race winners. He is the damsire of Forestry, sire of The Green Monkey sold at the February 2006Fasig-Tipton Florida auction for a world record price of $16-million. The Green Monkey had almost no success at the racetrack and is now standing at stud. Following his owner's death in 1997, Pleasant Colony was sent to Lane's End Farm in Versailles, Kentucky. Somehow in 2000 he was found in horrible conditions, very underweight and was brought to the KY Horse Park where he was given proper care. In 2000, he was pensioned and sent to Blue Ridge Farm in Upperville, Virginia, where he died in 2002 at age 24. Pleasant Colony returned to Buckland Farm, now owned by the Blake family, after his death and is buried on the farm overlooking the fields where his mares were.