The racetrack is nicknamed "Old Hilltop" after a small rise in the infield that became a favorite gathering place for thoroughbred trainers and race enthusiasts.

[2] Pimlico was owned by the Stronach Group from 2011 until 2024, when ownership transferred to the state-run Maryland Thoroughbred Racetrack Operating Authority (MTROA).

The track is also noted as the home for the match race in which Seabiscuit beat War Admiral in the second Pimlico Special, on November 1, 1938, before a crowd of 43,000.

A bill sponsored by the state racing commission in 1949 to abandon the track was originally supported by Governor William Preston Lane Jr., who reversed his position in late March.

It is an accepted American institution, devoted to the best interests of a great sport, graced by time, respected for its honorable past."

On March 23, 2010, an agreement was reached to sell the two Maryland Jockey Club tracks (Pimlico and Laurel Park) from Magna Entertainment Corporation to its parent company, MI Development.

On May 7, Penn National Gaming, with MI Development, announced they would jointly own and operate the Maryland Jockey Club.

Penn National bought a 49% stake in the Jockey Club in 2010 in hopes of securing a slots license at Laurel Park.

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 race track itself would be rotated 30 degrees in order to create nine parcels of land that could be sold for private development, and new barns for horses would be constructed.

[16] On March 14, 2024, the Stronach Group announced that it had reached a deal with the Maryland state government to transfer ownership of Pimlico to the new Maryland Thoroughbred Racetrack Operating Authority (MTROA), allowing for a multi-million dollar renovation project of the race course's track to begin and for the construction of a new training center at a separate location.

[17] The General Assembly passed a bill ratifying the deal in April 2024, which provided for $400 million in state bonds to be used for renovations to Pimlico.

[4] The new Maryland Jockey Club, as a non-profit entity of the MTROA, assumed control of thoroughbred racing in the state on January 1, 2025.

[22] Its name was altered, to Virgin Mobile Festival, when it returned to Pimlico on August 9–10, 2008, with five headliners: The Foo Fighters, Kanye West, Stone Temple Pilots, Jack Johnson, and Nine Inch Nails.

For major events, a shuttle is typically in place by the Maryland Transit Administration going to the race course from light rail and metro stations.