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Fancy Hats and the Chance to Win Big - Everything to Know About a Day of Horse Racing at the Preakness Stakes

The third Saturday of May every year is home to the Preakness Stakes, the second leg of thoroughbred horse racing's Triple Crown series.

By Becca van Sambeck

Most sporting events attract fanfare, but there's nothing quite like American thoroughbred horse racing. These races are known for their festive atmosphere (pour yourself a Black-Eyed Susan), the over-the-top fashion (think fascinators galore), and the bets (depending on whether gambling is legal in the state), making each occasion a real party.

Spring is the time for the most glamorous and important races: the Triple Crown series, which includes the Kentucky Derby (the first Saturday in May), the Preakness Stakes (the third Saturday in May), and the Belmont Stakes (the first or second Saturday in June). These races are for the best of the best when it comes to jockeys and horses alike.

To get a better idea of how horse racing works — and to experience all the festivities in person — NBC Insider headed to the 149th running of the Preakness Stakes, held on Saturday, May 18 at 2024 at the Pimlico Race Course in Baltimore, Maryland (which originally aired on NBC and you can currently watch on Peacock). What we learned? There's no event quite like it.

Here's everything to know about the Preakness:

How does thoroughbred horse racing work?

There are a variety of events held all over the country each year at different race tracks, where horses compete to be the fastest in a race.

These races include maiden races (horses who have yet to win a race), allowance races (these one will have various conditions regarding the horse's past), claiming races (where horses can be bought for a set price before the race even begins) and stake races (which is the highest level of competition, where the winning horse racks up prizes and honor).

The races range from short sprints to long distance (think 1 1/4 miles-plus) and can be run on a dirt track, turf (aka grass), or a synthetic track.

On the start of the day, all the horses are inspected by vets to ensure they're healthy and ready to run. Then, when it's time for their specific race that day, they do a quick parade for the spectators (who have likely placed bets on who they think will win each race). The horses head to the gates, where they await the starting signal. Then, they're off! The winner is whoever crosses the finish line first.

While the horse is obviously an extremely important element of the race, the jockeys who ride them during the race and the trainers who prepped the horses also share in the glory and prestige of a win.

What is the Triple Crown Series of horse racing?

The Triple Crown series are the three most important, prestigious thoroughbred horse races in America. They include the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes. Each event has its own reward, but it's especially impressive to win all three races, which makes one a Triple Crown winner. While it does happen, it's rare — the last Triple Crown winner was all the way back in 2018, when Justify took all three first-place trophies, according to NBC News.

What is the Preakness Stakes, and what makes it special?

The Preakness Stakes are the Middle Jewel — aka the second race — of the Triple Crown series of horse racing in America. The race is held in Baltimore, Maryland on the third Saturday of every May at the Pimlico Race course. However, the Preakness Stakes isn't just a day devoted to racing. It's also an incredibly exciting full-day music festival with concerts, food, drinks, and shopping.

"The Preakness is different than the Kentucky Derby. It's been referred to as the People's Party because it has a real history. We take the tradition of 149 years, and we have a lot of pomp and circumstance around what we do, and people get dressed up and wear the hats, and it's a big fashion moment as well. But at the same time, we try to modernize certain aspects, and really, it's a pop culture moment. We also highlight Baltimore, we celebrate Baltimore and the history there, too. We want people to have fun," Belinda Stronach, the CEO of the Stronach Group, which owns the Preakness Stakes, explained to NBC Insider.

This year, for example, various DJs and musicians performed, with Jack Harlow as the headliner. Previous years have seen artists like Post Malone and the Chainsmokers take the stage. Every 30 minutes or so, there's a race to watch, with people taking the time in between to enjoy music, eat — there are plenty of local Maryland vendors hawking state favorites like crab cakes and Old Bay seasoned-meals — drink, and check out various shopping stalls. We saw some very comfortable-looking Preakness hoodies on sale, as well as fancy hats if you forgot your fascinator at home!

The special drink for the Preakness is the Black-Eyed Susan, which features bourbon, vodka, peach schnapps, sour mix, and orange. Make sure to drink responsibly, though: As one bartender at Preakness Stakes warned us, "It's a bit like a Long Island Iced Tea, with all the various alcohols."

Attendees also use the down time between events to place their wagers, which helps viewers get even more involved in the races. There are 14 total at the Preakness.

"There's something for everyone. The days are gone where you just sat in your seat and didn't move around. You can really move around and experience a whole bunch of different things," Stronach said. "It combines fashion, food, people that are having a good time and want to have fun. The wagering aspect adds to the camaraderie and the competitive dynamic."

How does horse betting work?

If you want to get in on the wagering, you'll find it's much easier — and can cost less money — than you probably expect. While there are stations all over Preakness with attendants to help you place your bets, you can also place them through an app, 1/STBETS. This means you can do it all through your phone, checking out each horse's odds and learning more about their history to pick your wagers.

There are several different kinds of bets you can make, although as a first-time wagerer, we were recommended to try win, place, or show bets. That means you put money down on a horse coming in first, second, or third place.

Simply put, if you bet for a horse to win, it means it'll finish first. If you bet on it to place, it'll come in first or second. If you bet on it to show, it means it'll come in first, second, or third.

There are also more detailed kind of bets like the Exacta (which means you predict the top two in order), the Trifecta (the top three in order), and even the Superfecta, which is the first four finishers.

You can place money on multiple horses for each race, and the amount is totally up to you. While we only placed $2 on two horses in each race (which led to a small payout at the end of the day!), others put hundreds or even thousands of dollars on their favorite horses. 

Of course, while you can try to check out all the horses' odds and skim over their background to select the winner, it can be more lucrative to place your money on an underdog horse, as you'll get a larger payout if the horse beats the odds and fulfills your wager.

Plus, as one Preakness attendant explained to us, sometimes, it's best to just go with the horse name you like the most (and with names like Mystik Dan and Tuscan Gold, you'll definitely be delighted by several of them). Anything can happen to impact the race, so it's difficult to actually predict a winner.

What should you wear for a Kentucky Derby, Preakness Stakes, or Belmont party?

When you think of these events, you likely picture one key fashion statement: a hat. And it's true that whether you're at these events in person or attending a viewing party, you'll see a lot of large, elaborate hats. It's not mandatory but it's definitely a way to get in on the fun!

Others opt for florals, linens, and springtime colors for their Preakness wardrobe. Think bright, cheerful, and slightly more upscale — suits for men, dresses or pantsuits for women.

"Every year, I'd say it gets more colorful, and people get more and more into it. Women wear dresses and hats, a lot of color. The men, same thing, lots of colorful bow ties, pink suits. I think it just reflects people's mood and desire to have fun and join in the festivities," Stronach said.

Still, nothing is mandatory, and in fact with unpredictable weather, it can be best to dress sensibly. Many people chose to wear boots or sneakers this year due to the rainy weather and muddy grounds, and paired jackets with their look.

Who won the Preakness Stakes this year, and will there be a Triple Crown winner?

This year, Seize the Grey took home the top prize at Preakness. However, since Mystik Dan (who came in second) previously won the Kentucky Derby, there will not be a Triple Crown winner in 2024.

If you want to keep an eye on future horse races, tune into Peacock, which airs various ones throughout the years.

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