Painting by Edward Troye
Longfellow was an enormous colt, nearly 17 hands, and was unraced at 2 while Harper waited for the colt to mature into his size. When asked if the colt was named for the author Longfellow, Harper replied: "Never heared much of that feller but that colt of mine's got the longest legs of any feller I ever seen."
Longfellow's racing career began in the spring of his 3-year-old season, but he was found to be too awkward. He was turned out for the summer and then came back for an excellent fall season. Thereafter, his prowess on the track was unquestioned.
In the fall of his 3-year-old season, Longfellow won the Produce and the Ohio Stakes. He was then shipped to Nashville for the Citizens' Stakes and to Memphis for the Post Stakes. He won both of these races.
In his first race at 4, Longfellow had no competition and won in a walkover. He was then shipped east to win the Monmouth Cup, the Saratoga Cup, and a match against Pilgrim. Longfellow's final season was marked by his rivalry with the eastern champion Harry Bassett. In their first meeting, Longfellow won by over 100 yards after Harry Bassett went into a sulk. They met again in the Saratoga Cup. On his way to the post, Longfellow twisted a shoe. He lost by only one length and left the track limping on three legs; this was his final race.
At stud Longfellow sired four champions and at least 42 stakes winners. The champions included The Bard, Freeland, Longstreet, and Thora.
Longfellow was inducted in the Hall of Fame in 1971.
Longfellow's match with Harry Bassett, Print by Currier and Ives