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Pimlico Picks, Tips and Handicapping

Written by: Brian Zipse
Updated October 14, 2022
10 min read
Pimlico Racetrack



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As the longtime home of the Preakness Stakes, the middle leg of racing’s Triple Crown, Pimlico Race Course holds a special place among American racetracks. Pimlico first held the Preakness back in 1873, and after a brief sabbatical, it’s been the site of the historic race every year since 1909.

Nearly 150 years since the inaugural edition, the Preakness maintains its place as one of the most important events in American racing. In recent years, no race has been more vital in identifying the Champion 3-year-old Male. In fact, 16 of the last 22 Preakness winners brought home an Eclipse Award the same year, starting with Silver Charm in 1997.

Also known as “Old Hilltop”, Pimlico not only has the Preakness, but it also plays host to numerous other important races in May, including the female counterpart to the “Middle Jewel”, the Black-Eyed Susan, as well as the historic Pimlico Special and Dixie Stakes.

Fast Facts:

  • Location: Baltimore, Maryland
  • Built-in: 1870
  • Nickname – Old Hilltop
  • Owned by: The Stronach Group
  • Track Type: Main track dirt – Inner track turf
  • Dirt Track Length: One mile
  • Turf Track Length: 7/8 of a mile
  • Capacity: 140,000 (Including infield)
  • The Preakness is restricted to horses 3-years-old
  • Preakness stakes record: Secretariat (1973) 1:53
  • Preakness largest winning margin: Smarty Jones (2004) 11 ½-lengths
  • The Black-Eyed Susan is restricted to female horses 3-years-old
  • Black-Eyed Susan stakes record: Silverbulletday (1999) 1:47.83
  • Major Events: The Preakness Stakes, Black-Eyed Susan Stakes, Pimlico Special, Dixie Stakes

Pimlico Race Course At a Glance

Located in Baltimore, Maryland, Pimlico Race Course will forever be best known as the home of the Preakness Stakes. As racing’s “Middle Jewel”, the race stands tall as the cornerstone of Mid-Atlantic horse racing.

As home to the Preakness, Pimlico is the focal point of not only bringing the best 3-year-old horses in the country to Baltimore, but also hundreds of thousands of fans to the city to celebrate horse racing, and all things Maryland.

The venue itself is one of the oldest racetracks in the United States, with a capacity of up to about 140,000 when the infield is open, as it is on Preakness and Black-Eyed Susan day.

Known for its tight turns as compared to Churchill Downs and Belmont Park, an assumption often argued each spring when the Preakness rolls around, the track continues to be known as “Old Hilltop”.

The nickname stems from the hill which the track was originally built around. Eventually, Alfred G. Vanderbilt, the track president at the time, and the future owner of the 1953 Preakness great, Native Dancer, had the hill in the infield leveled to offer better viewing of the backstretch for all patrons of Pimlico.

Today Pimlico is only open for racing for a short time, with Laurel Park being the regular host of Maryland racing throughout the year. What it lacks in overall racing, though, Pimlico makes up for in history and a number of important races in May.

Pimlico History

Pimlico Race Course was born out of a lavish dinner party following the races at Saratoga in 1868. Wanting to commemorate the evening, which was attended by several racing enthusiasts, including Maryland’s Governor Oden Bowie, the distinguished gentlemen hatched a plan to create the Dinner Party Stakes.

Bowie promised to deliver a big purse for the new race and insisted the event should take place in his home state of Maryland. To follow through on these plans, he soon began construction on a new racetrack to host the race. Pimlico Race Course, named after the area where it stands, which was derived from a tavern owner in London, was the result, and it was open for business by the fall of 1870.

Sure enough, opening day at Pimlico featured the rich Dinner Party Stakes, and the winner of that inaugural edition was a horse named Preakness. The Dinner Party Stakes would eventually become known as the Dixie Handicap, which remains a traditional stakes race on the turf each spring. It is one of the oldest stakes races still run in America.

Three years after Preakness won the first Dinner Party, and two years before the first Kentucky Derby, Pimlico introduced its brand new stakes race for 3-year olds. The inaugural edition was won by Survivor, and the Preakness has been an important race ever since.

Traditions of the Preakness

With a history older than even the Kentucky Derby, the Preakness is full of tradition. Contested each year on the third Saturday in May, the event combines great horses and racing with a good mix of its roots of Baltimore and Maryland. A visit to Pimlico for the Preakness is sure to make a memory to last a lifetime. Below are some of the most famous traditions connected to the Preakness.

The Most Valuable Trophy in American Sports

While the winner of the Preakness each year receives a smaller sterling silver replica, which is still valued at $30,000, the official trophy of the “Middle Jewel” is legendary in its own right. Standing 34 inches tall and weighing in at just under 30 pounds, the Woodlawn Vase is easily the most valuable trophy in American sports. The original is on display at The Baltimore Museum of Art throughout the year, but is brought to Pimlico Race Course each May for the annual running of the Preakness.

Partying at Preakness InfieldFest

In recent years the Preakness InfieldFest has become one of the biggest parties associated with racing. During Preakness Week, fans from around the country, and the world, come to Baltimore and Pimlico Race Course to celebrate racing and have a good time. The week culminates with InfieldFest on Preakness Day, which attracts numerous well-known performers and bands.

Of course, it wouldn’t be the Middle Jewel without a little drinking and gambling. Cashing a ticket on the Preakness is always an extra thrill, but trying the Black-Eyed Susan, the official cocktail of the big race, is a must. Said to include bourbon, vodka, and peach schnapps, it only adds to the party scene that is the Preakness.

Maryland, My Maryland

What “My Old Kentucky Home” is to the Kentucky Derby, “Maryland, My Maryland” is to the Preakness. The official state song, it is ceremoniously played each year as the horses make it onto the track. Actually used as a battle hymn during the Civil War, the Pimlico crowd joins in the singing of the song, which is usually performed by the United States Naval Academy Glee Club.

The Run for the Black-Eyed Susans

Every winner of the Preakness since Bimelech in 1940 has been awarded a blanket of Black-Eyed Susans in the Pimlico winner’s circle. The state flower of  Maryland for more than a century, they actually do not bloom until a little later in the season. Instead the prized blanket is made from daisies which are painted to look like Black-Eyed Susans.

Painting the Weather Vane

One of the most familiar sights each year after the running of the Preakness is the painting of the infield weather vane. Immediately after the race is made official, an artist rises up in a hydraulic lift to complete the annual tradition of applying the colors of the winning owner’s silks on the jockey and the numbering of the winning horse’s saddlecloth as part of celebration of the new champion. The weather vane stays in those colors until the next year’s Preakness.

The Second Leg of the Triple Crown

The Preakness Stakes is one of the most important horse races in America, but it is also the middle leg of the most prestigious series in racing. Proceeded by the Kentucky Derby, two weeks earlier at Churchill Downs, and then followed by the Belmont Stakes, three weeks later at Belmont Park, the three legs of the series comprise the Triple Crown.

Winning the Preakness gets your name in the history books, but completing the Triple Crown sweep ensures immortality.

The 13 horses to sweep the series of the Kentucky Derby, Preakness and Belmont Stakes are:

Year Horse
1919 Sir Barton
1930 Gallant Fox
1935 Omaha
1937 War Admiral
1941 Whirlaway
1943 Count Fleet
1946 Assault
1948 Citation
1973 Secretariat
1977 Seattle Slew
1978 Affirmed
2015 American Pharoah
2018 Justify

Legends of Pimlico

Over the years, many of the greatest horses in the history of American racing have run at Pimlico Race Course.

Man O’ War, Native Dancer & Spectacular Bid

While the winners of the Triple Crown will forever have their place in history, some of the greatest horses in American history were not among the 13 horses to sweep the series. Man O’ War did not run in the Kentucky Derby, Native Dancer suffered his only career defeat when just missing in the Derby, and Spectacular Bid stepped on a safety pin the morning of the Belmont. All three, though, count the Preakness among their most important career wins. The most recent of the three, Spectacular Bid actually began his career at Pimlico, winning easily his first two career races there in the summer of 1978.


Of the 13 horses that did sweep the Triple Crown, none is more famous than Secretariat. The son of Bold Ruler, who won the Preakness himself in 1957, made an early and unprecedented move in the “Middle Jewel”, exploding on the first turn to go from last to first in a matter of seconds. He set a Preakness record of 1:53, but due to a malfunction of the track timing mechanism, his time did not become official for another 39 years.

The Match Race (Seabiscuit vs. War Admiral)

Perhaps the most famous of all races at Pimlico was not actually a Preakness, but rather came in the second-ever edition of the Pimlico Special.

In what was billed as “The Race of the Century”, America’s best horses squared off in a ballyhooed 1938 match race. Seabiscuit was the rags to riches champion from California, while War Admiral was a Triple Crown winner and son of the great Man o’ War. War Admiral had also won the inaugural edition of the Pimlico Special the year before.

Unexpectedly, it was Seabiscuit who broke fast and shot right out for the early lead, which is almost always an advantage in a match race. War Admiral pulled even on the outside down the backstretch, but when they turned for home it was the West Coast horse who proved stronger on this day.

Seabiscuit won the 1 3/16-mile race by four lengths, and in record time. He also became the second Pimlico Special winner to be named Horse of the Year in as many years.

Notable Jockeys & Trainers

On the human side, Mario Pino is the all-time leading rider in Maryland, with nearly 5,000 wins at the state’s racetracks. Known for his consistency and character he finished in the top five of the state standings for 25 straight years from 1979 to 2003. A Mike Venezia Award winner, he is perhaps best known as the rider of Hard Spun, who finished second in the Kentucky Derby and third in the Preakness of 2007.

As far as the Preakness, legendary jockey Eddie Arcaro holds the record for most wins with six. Two of them (Whirlaway and Citation) were Triple Crown winners, and his last victory in the race came with Bold Ruler in 1957.

Pino’s training counterpart is King Leatherbury, who remains a living legend on the Maryland circuit. The University of Maryland graduate has won more than 50 training titles combined at Pimlico and Laurel Park. At 87-years-old, the Hall of Famer is still training today.

Two trainers have won the Preakness seven times. Robert Wyndham Walden dominated the first quarter-century of the race back in the 19th century, and much more recently Bob Baffert matched his record, including two Triple Crown champions, American Pharoah and Justify.



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Brian Zipse

Horse Racing Betting Analyst

Horse Racing
Betting Picks
Taken to the races at a very young age, Brian has been a passionate fan of horse racing his entire life. Professionally, his work has been published on several leading industry sites. Brian served as the Editor of Horse Racing Nation from 2010-2017, where he still writes a regular column and hosts the popular weekly webcast HorseCenter.
Nationality: American
Education: Bachelor of Communications
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