A Beginner’s Guide to the Preakness Stakes

Events / Travel
A fan at Pimlico looks at the program on Preakness day in 2019. (Penelope P. Miller/America's Best Racing)

For a race that has 146 years of history behind it, the Preakness Stakes is an incredibly modern even. Half elite day of horse racing, half festival, the middle jewel of the Triple Crown (comprised of the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes) has evolved into a destination event for sports and music fans across the country.

If you’re new to the Preakness Stakes, we have the answers to your most important questions about Baltimore’s biggest party.

WHO: Elite 3-year-old Thoroughbreds … male and female

Swiss Skydiver winning 2020 Preakness Stakes against males. (Eclipse Sportswire)

The Preakness is the middle jewel of the Triple Crown; and while the Kentucky Derby can boast three female winners, the Preakness has welcomed six fillies to its winner’s circle: Flocarline (1903), Whimsical (1906), Rhine Maiden (1915), Nellie Morse (1924), Rachel Alexandra (2009), and Swiss Skydiver (2020).

WHAT: The middle jewel of the Triple Crown and the party that comes along with it

The Preakness is especially exciting because it’s the race that determines whether we’ll be rooting for a Triple Crown winner again in 2021. All eyes will be on Pimlico Race Course in Baltimore on the third Saturday in May to see whether Medina Spirit can cover 1 3/16 miles faster than the competition.

The Preakness also offers up the most valuable trophy in all of sports: the divine Woodlawn Vase was originally created in 1860 by Tiffany and Company and was assessed in 1983 to be valued at $1 million … that’s $2,659,407.63 in 2021 when adjusted for inflation.

WHEN: The third Saturday in May … usually

The Preakness Stakes has traditionally been run two weeks after the Kentucky Derby, which (almost) always occurs on the first Saturday in May. There are exceptions, though: due to the pandemic, the 2020 Preakness was on Oct. 3; additionally, while the Preakness has been run on a Saturday every year since 1931, it has gone off on every day of the week except for Sunday. In its long history, the Preakness has been held on Tuesday 14 times, Friday 13 times, Monday six times, Wednesday five times, and Thursday four times.

WHERE: Pimlico Race Course in Baltimore

The Maryland Jockey Club actually predates the United States of America: the former was founded in 1743 and the latter in 1776, making the Maryland Jockey Club the oldest sporting association in the country. Racing began at present-day Pimlico in Baltimore in 1870, and the very first Preakness Stakes was run in 1873.

WHY: There was a really, really fun dinner party in 1868

You know how sometimes you go to what you think is going to be a quiet dinner with friends and the evening sort of gets a lot bigger than you thought it was going to get? That happened in 1868 when a group of horse owners got together in Saratoga Springs, N.Y. after the races one summer evening. The dinner party was so much fun that attendee John Hunter proposed that the party be commemorated by running a horse race in the fall of 1870 for 3-year old Thoroughbreds called Dinner Party Stakes. Maryland’s then-Governor Oden Bowie upped the ante, suggesting that the purse of the race be $15,000 (that’s $263,157.89-ish in 2021) and that the race should be held in Maryland. He even promised to build a new racetrack to host the event, and Pimlico Race Course was born. The very first horse to win the race was Preakness in 1870, and the rest, as they say, is history.


After what I think we all can agree was a pretty weird 2020, the Preakness is back to its usual spot on the third Saturday in May. Tickets are available, and if you’re planning to attend, the Preakness has a great resource for safety and health guidelines here. Click on the link to the left of this copy to receive a 10 percent discount on tickets to Preakness Live by using the promo coce ABR10; the discount code is also available for tickets at the Turfside Terrace

You should also check out the list of what you can and cannot bring into Pimlico on Preakness day to make sure you aren’t running laps from your car to the track instead of enjoying a day at the races. Leave your drones and balloons at home, friends.

Planning to watch at home? NBC coverage of the middle jewel of the Triple Crown begins on Friday, May 14 at 5 p.m. ET on NBCSN.  On Saturday, May 15, NBC will show the Preakness beginning at 5 p.m. ET, with coverage also beginning at 2 p.m. ET on NBCSN. 


Did you fall in love with Medina Spirt, the horse that sold for $1,000 as a one-year-old and went on to win the Kentucky Derby? He’s coming to the Preakness! If he’s not your horse, don’t worry: you’’ll likely have nine more chances to fall in love before May 15 since 10 horses are probable to run in the Preakness.


A fan at 2019 Preakness. (Penelope P. Miller/America's Best Racing)

It’s incredibly easy to bet the Preakness Stakes, even if you’re not able to attend. It’s legal in 37 states to bet from home using what’s called an “advance deposit wagering” platform – essentially an app or website that allows you to load up your account and bet from wherever you like. One piece of advice: the key word here is “advance,” so make sure to set your account up as early as possible since sometimes it takes a day to process the funds.

Speaking of betting online, can I recommend 1/ST Bet? Not only are they the official digital wagering platform of the Preakness, but they also sponsor our Gambling Calculator which will help you figure out the costs of your bet. Also, if you sign up for 1/ST Bet using promo code 500ABR, new players will receive a special offer that will start you out with up to a $500 bonus.

The team at America’s Best Racing also put our heads together to provide some Dos and Don’ts for betting online. We even have the leading tool in the sport for figuring out how to make your bets and what they’ll cost: ABR’s Gambling Calculator, presented by 1/ST Bet.

If you’re new to betting on horse racing, welcome! We’re here to help. If you need some information on how to start, we have a post called “Betting on Horse Racing, Explained” with a focus on bettors just like you. Here’s a taste to whet your appetite:

The Basics

Win bet – A bet on a horse to finish first.

Place bet – A bet on a horse to finish first or second.

Show bet  A bet on a horse to finish in the money; third or better.

In the money – A horse that finishes first, second, or third.

Across the board – A bet on a horse to win, place, and show. If the horse wins, the bettor collects three ways; if second, two ways (place, show); and if third, one way, losing the win and place bets. It's actually three bets.

Morning line – The odds that the track handicapper predicts a horse will be to win the race when it starts.

Did you Know? - The record for money bet on Preakness Stakes day was in 2019 when $99,852,653 was wagered on racing from Pimlico that day.


The Preakness has become one of the biggest parties of the spring since the inception of InfieldFest in 2010, which combines a two-day-long music festival with some of the best horse racing in America. Past headliners have included Lorde, Childish Gambino, Sam Hunt, Zedd, The Chainsmokers, Maroon 5, Bruno Mars, Fetty Wap, and Armin van Buuren.

Though InfieldFest 2021 has been canceled due to the pandemic, Pimlico has reimagined the festival experience with Preakness LIVE. With a limited crowd of 10,000, the Preakness LIVE lineup includes D-Nice, 2 Chainz, and Jack Harlow.


Cloud Computing in 2017 with winner's garland. (Penelope P. Miller/America's Best Racing)

Horse racing is a sport often defined by its traditions, and the Preakness has some great ones. For example, the Preakness’s sister race, the Black-Eyed Susan, is held the Friday of Preakness week; the Black-Eyed Susan is also the official cocktail of the Preakness as well as the type of flower that makes up the garland that adorns the race winner’s neck. Other traditions include painting the silks on the jockey at the top of the replica of the Old Cupola in the Preakness winner’s circle as soon as the race becomes official. There’s also a singalong of “Maryland, My Maryland” as the Preakness runners head to the starting gate in what is known as the post parade.

One of the great traditional events of Preakness week is the Alibi Breakfast, an annual brunch that earned its name because of the tall tales told by racetrack folks – big bets, big payouts, and big loss stories usually can’t really be corroborated, but everyone tries to come up with an alibi. Nowadays, it’s a gathering of the owners, trainers, and jockeys participating in the Preakness swapping stories about their horses and mingling with fans and media.


Racehorses come in many different sizes, ranging from about 900 to 1,400 pounds, and colors, including Bay, Black, Chestnut, Dark Bay or Brown, or Gray or Roan. There also has been in recent years an increase in White Thoroughbreds. Many racehorses stand out because of markings, like a white blaze or star on their heads or one or more white legs or feet. When a Thoroughbred is born, it is called a foal, which is a name for a young horse in the first year of its life. Thoroughbreds are called weanlings after they have been separated from their mothers; and a yearling refers to a male or female Thoroughbred in its second calendar year of life, which commences Jan. 1 of the year following its birth, and Jan. 1 is the official birthday for all Thoroughbreds. All Thoroughbred racehorses must be registered according to the guidelines of The Jockey Club and races begin for racehorses in the spring of their 2-year-olds seasons.

Did You Know? More than half of the Preakness Stakes winners have been Bay (brown coat with a black mane and tail) with 76 of 145 winners to the color’s credit.


Some of the best male and female racehorses go on to a breeding career in retirement, but only the best male racehorses become sires (fathers) and roughly 27,000 to 33,000 female Thoroughbreds are bred each year. The good news is Thoroughbred racehorses are incredibly versatile and often go on to second careers at what is called OTTBs (off-track Thoroughbreds).

Thoroughbreds are smart, competitive animals and if they’ve spent time stabled at a racetrack, which the vast majority have, they’ve seen and heard pretty much everything. Retired racehorses can go on to second careers in Dressage, Eventing, Show Jumping, Polo, etc. Each year the Retired Racehorse Project hosts the Thoroughbred Makeover, the largest Thoroughbred retraining competition in the world for recently-retired ex-racehorses. OTTBs can become pleasure horses and sometimes they just live a life of leisure, ranging from those at Old Friends in Georgetown, Ky. to others who simply get adopted by someone who followed their career or loves horses. In recent years, studies have also shown racehorses can be powerful partners for therapy, including Equine-Assisted Therapy for treating veterans with PTSD and the Square Peg Foundation for students. The Thoroughbred industry created the Thoroughbred Aftercare Alliance, funded initially by Breeders’ Cup Ltd., The Jockey Club, and Keeneland Association. The TAA is a 501(c)(3) nonprofit that accredits, inspects, and awards grants to approved aftercare organizations to retrain, retire, and rehome Thoroughbreds using industry-wide funding. Since 2012, the TAA has granted more than $20.7 million to accredited aftercare organizations and 11,000 Thoroughbreds have been retrained, rehomed, or retired by accredited organizations.

For much more on this topic, visit our Horses First page.

One Preakness runner who has gone on to great success off of the track is Icabad Crane, who finished third in the 2008 running and is owned and campaigned by Olympic equestrian Phillip Dutton.


Exaggerator winning the Preakness. (Eclipse Sportswire)

  1. Two Preakness-winning jockeys have gone on to train Preakness winners: Louis Schaefer won the race in 1929 aboard Dr. Freeland and then conditioned Challedon to victory in 1939. In 1943, Johnny Longden piloted Count Fleet to the winner’s circle on the way to capturing the sixth Triple Crown title in history. Longden went on to train Majestic Prince to a Preakness win in 1969.
  2. The Preakness has been run before the Kentucky Derby on 11 occasions and twice the races were held on the same day.
  3. There have been only three horses who won the Preakness and had undefeated 3-year-old seasons: War Admiral (1937), Count Fleet (1943), and Justify (2018).
  4. Ten Preakness winners have sired Preakness winners. They are: Bold Ruler (Secretariat); Bold Venture (Assault); Gallant Fox (Omaha); Man o’ War (War Admiral); Polynesian (Native Dancer); Citation (Fabius); Native Dancer (Kauai King), Secretariat (Risen Star), Summer Squall (Charismatic), and Exaggerator (Curlin).
  5.  In 1918, 26 horses entered the Preakness Stakes, causing the race to be run in two divisions for the first and only time in history.

newsletter sign-up

Stay up-to-date with the best from America's Best Racing!