Two years before the Kentucky Derby was run for the first time, Pimlico introduced its new stakes race for three-year-olds, the Preakness, during its first-ever spring race meet in 1873. Then Maryland governor Oden Bowie named the then mile and one-half (2.41 km) race in honor of the colt Preakness from Milton Holbrook Sanford's Preakness Stud in Preakness, Wayne Township, New Jersey, who won the Dinner Party Stakes on the day Pimlico opened (October 25, 1870). The New Jersey name was said to have come from the Native American name Pra-qua-les ("Quail Woods") for the area. After Preakness won the Dinner Party Stakes, his jockey, Billy Hayward, untied a silk bag of gold coins that hung from a wire stretched across the track from the judges' stand. This was the supposed way that the "wire" at the finish line was introduced and how the awarding of "purse" money came to be. In reality, the term "purse", meaning prize money, had been in use for well over a century.
Sir Barton, winner in 1919
The first Preakness, held on May 27, 1873, drew seven starters. John Chamberlain's three-year-old, Survivor, collected the $2,050 winning purse by galloping home easily by 10 lengths. This was the largest margin of victory until 2004, when Smarty Jones won by 11 1/2 lengths.
In 1890 Morris Park Racecourse in the Bronx, New York hosted the Preakness Stakes. This race was run under handicap conditions, and the age restriction was lifted. The race was won by a five-year-old horse named Montague. After 1890, there was no race run for three years. For the 15 years from 1894 through 1908, the race was held at Gravesend Race Track on Coney Island, New York. In 1909 it returned to Pimlico.
Seven editions of the Preakness Stakes have been run under handicap conditions, in which more accomplished or favored horses are assigned to carry heavier weight. It was first run under these conditions in 1890 and again in the years 1910-1915. During these years, the race was known as the Preakness Handicap.
In March 2009 Magna Entertainment Corp., which owns Pimlico, filed for Chapter 11 bankruptcy thus throwing open the possibility the Stakes could move again. On April 13, 2009, the Maryland Legislature approved a plan to buy the Stakes and the Pimlico course if Magna Entertainment cannot find a buyer.
Attendance at the Preakness Stakes ranks second in North America and usually surpasses the attendance of all other stakes races including the Belmont Stakes, the Breeders' Cup and the Kentucky Oaks. The attendance of the Preakness Stakes typically only trails the Kentucky Derby, for more information see American Thoroughbred Racing top Attended Events.
In February 2017, the Maryland Stadium Authority released the first phase of a study saying that Pimlico needed $250 million in renovations. As of May of that year, no one showed interest in financing the work. The Stronach Group, owner of Pimlico Race Course and Laurel Park, was only interested in moving the Preakness Stakes to Laurel Park unless someone else financed work on Pimlico.
In October 2019, The Stronach Group reached an agreement in principle with the city of Baltimore and groups representing Maryland horsemen that would permanently keep the Preakness at Pimlico. As part of the agreement, Pimlico's grandstand would be demolished and replaced with a smaller structure, and temporary seating would be added to handle the attendance during Preakness week. The plan would have to be approved by the Maryland state legislature when they convene in 2020, as existing state laws would have to be modified in order for the proposal to be realized.