Whimsical (foaled 1903 at Catesby Woodford's Raceland Farm near Paris, Kentucky) was an American Thoroughbred racehorse. She is best known as the second filly to ever win the Preakness Stakes.

Background

Whimsical was sired by Orlando, out of the mare, Kismet, who was sired by United States Racing Hall of Fame stallion, Hindoo.^[2]

Racing career

As a two-year-old Whimsical won the Belles Stakes and Golden Rod Stakes at Sheepshead Bay and finished second when racing against colts in the Champagne Stakes. At age three she won the Standard Stakes at Gravesend in which she defeated 1905 Preakness Stakes winner Cairngorm and 1905 Futurity Stakes winner Ormondale. In the Preakness Stakes she led from the start and won easily^[3] in a time of 1:45 by 4 lengths over Content and Larabie. In this period, the race was held at Gravesend Race Track on Coney Island, New York.

Owner Tim Gaynor sold Whimsical to the partnership of Matthew Looram and a Mr. Biddle. The new owners maintained Gaynor as Whimsical's trainer until late August 1907 when they replaced him with Frank Weir.^[4][5]

Retirement

Whimsical was retired to Brookdale Farm to become a broodmare.^[6]

Honours

The Whimsical Stakes at Pimlico Race Course is a 6 furlong race named for her and is raced on Preakness weekend.

Pedigree