Off Track betting on the Preakness Stakes

The Triple Crown is horse racing’s biggest stage — three races that define legacies, rewrite history, and move serious money. The Preakness Stakes sits right in the middle of it all, and by the time the field storms into Pimlico, everything is on the line. For bettors, this isn’t just a race — it’s a high-stakes opportunity loaded with angles, odds, and outs.

This guide was built for that moment. Not some surface-level breakdown or recycled list — but a full-scale blueprint for how to bet the Preakness Stakes the right way. We’ve tested every sportsbook that matters and hand-picked our favorites based on criteria that truly moves the needle for bettors. If you’re serious about turning the Preakness into a profit machine — or just want to bet smarter than the crowd — this is your starting gate. From first click to the final stretch, this guide has you covered.

Best Offtrack Preakness Stakes Racebooks

Let’s be honest — every sportsbook on the internet says they’re your go-to destination for Preakness Stakes betting. They’ll throw around buzzwords, fancy promos, and call it a day. But when it’s time to actually bet the race and get value for your money, most of those books fall flat. That’s why we put this list together — a real-deal breakdown of the best places to bet the Preakness online. If you can only bet at three or so spots, then make it one of these:

BetOnline

Few bookies outdo BetOnline when it comes to betting on the Preakness Stakes. This book comes to life when the stakes are high, offering a deep and well-structured racebook that caters to seasoned handicappers and casual race-day bettors alike. If you want options, value, and speed all in one place, BetOnline checks every box.

You’ll find every Preakness Stakes betting type covered — win, place, show, exacta, trifecta, superfecta — but what makes BetOnline standout is how seamless it is to stack these into creative betting strategies. Want to box your top three horses? Key a longshot under a favorite? BetOnline’s system handles complex bets with ease, giving you full control of your card without the usual platform headaches.

Another huge asset is how quickly BetOnline posts its best bets for Preakness Stakes. You’re not stuck waiting for the dust to settle from the Kentucky Derby — BetOnline has markets ready to go early, giving sharp bettors a chance to get in before the public starts pushing prices around. After all, early bird gets the worm (or value in this case).

The betting odds themselves hold up too. BetOnline has earned a reputation for offering competitive lines across sports, and horse racing is no exception. Whether you’re locking in a favorite or throwing a Hail Mary on a longshot, you won’t feel like you’re paying a premium just to lay money on the online betting Preakness Stakes opportunities.

From front to back, BetOnline feels like a sportsbook that understands how to treat a major racing event. It’s fast, reliable, and offers enough flexibility for bettors to approach the big race however they see fit. If you want a clean, high-powered experience that won’t let you down on race day, this one’s a must-use.

Bovada

Bovada has long been one of the most dependable names in the offshore betting world — and its presence in the horse racing space is no exception. While some books try to draw attention with loud marketing or over-the-top features, Bovada just delivers where it counts: reliability, betting depth, and a smooth experience on any device. For an event like the Preakness Stakes, that kind of consistency matters.

The race-day betting menu is dialed in from top to bottom. You’ll find win, place, and show bets — naturally — but Bovada also opens up deeper pools for bettors looking to press an edge. That includes exactas, trifectas, superfectas, and even matchup-style bets that let you pit one horse against another. It’s a nice variety that makes Bovada feel built for the full spectrum of race fans, not just casuals.

Odds-wise, Bovada competes with the best of them. They don’t just follow the market averages — this is a book that sharpens its lines and offers real value. Especially on a high-profile race like the Preakness, where millions flood the markets and prices fluctuate, having a site that holds the line well is a big plus. Whether you’re backing a heavy favorite or hunting a juicy longshot, Bovada gives you a fair shake.

Another underrated aspect of Bovada is the interface. Clean layout. No lag. Glitches almost nonexistent. Just a dependable site that moves quickly from bet slip to confirmation. That applies to both desktop and mobile, which is important when you’re watching the Preakness with friends or on the go. For a fast-paced race, the last thing you want is a clunky interface — Bovada avoids that trap.

In short, Bovada’s not trying to reinvent horse betting. It’s just doing the fundamentals right. That makes it one of the best all-around options for anyone betting the Preakness — from sharp bettors to someone making their first wager on a Triple Crown race. It’s smooth, smart, and steady — the trifecta you want behind your picks.

WagerWeb

WagerWeb is one of those rare racebooks that keeps a low profile but quietly delivers everything a serious horseplayer could want. Its horse betting menu is sneakily deep — not just offering the basics like win-place-show, but also covering exactas, trifectas, daily doubles, and more. Whether you’re building out a big Preakness Stakes betting card or just looking to fire a quick play on your favorite longshot, WagerWeb’s layout makes it easy to scan and act fast without feeling overwhelmed.

One of WagerWeb’s biggest perks is its 5% weekly rebate on racebook losses. That might sound small at first, but it adds up fast — especially if you’re betting throughout the Triple Crown season. When you have a rough go (which is bound to happen in betting, unfortunately), this rebate means you’re always getting a slice back, which helps extend your bankroll and keeps you in the action longer. And the best part? It’s automatic. No hoops to jump through, no promo codes to enter. Just a steady stream of value for active bettors.

WagerWeb also takes a unique approach with its deposit bonuses. Instead of locking users into a single offer, the site uses a progressive system — the more you deposit, the better the bonus you’ll unlock. This rewards high-stakes players who want to come in with more firepower, but still leaves solid value for smaller bettors who just want to ease in. It’s a “more skin in the game, more rewards” mentality that fits well with the energy of big-race days like the Preakness.

Taken together, these features make WagerWeb a strong pick for bettors who value long-term value and smart incentives. From its underrated betting menu to its automatic rebates and flexible bonus structure, the site gives you every reason to stick around and keep firing. 

Why Are These The Best Preakness Stakes Betting Sites?

We took the above suggestions super seriously. No kidding, we’ve tried out well over 100 betting sites. 100! After testing out so many, the great ones start standing out, especially in certain qualities we think bettors should NEVER settle on. Here’s why we picked the betting sites that we do (and skipped out on others):

Reputation and Trust

If a sportsbook doesn’t have a strong track record, it’s out of the running (pun intended). Every site we recommend here has proven itself over time. They process withdrawals fast, offer fair support when issues come up, and operate transparently. That might sound basic, but in the offshore world of horse racing betting, it’s not. There are still too many seedy operators out there, but not the ones mentioned here. We’ve used these books ourselves and wouldn’t list them if we didn’t trust them with our own money.

Deep Racing Menus

Any betting site can offer a win bet. But what’s the fun in such a simple bet? That’s why we looked for books that offer a wide range of Preakness betting options — exactas, trifectas, superfectas, head-to-head matchups, futures, and live odds. The more variety they have, the more strategy they can bring to your betting. These sportsbooks give you plenty of tools to build creative tickets and take advantage of the day’s full race card, including the early ones.

Mobile Speed and Stability

You’re not always betting from a desk — and the best sportsbooks understand that. Whether you’re at the track, out with friends, or checking odds between errands, your betting site needs to work wherever you are and on whatever screen you’re using. The platforms we chose are built for that kind of flexibility. They adapt cleanly to phones, tablets, and everything in between. No awkward formatting. No broken layouts. Just a smooth experience that lets you bet without fuss.

Bonuses & Promotions at the Top Preakness Stakes Racebooks

The Preakness Stakes isn’t just a premier race — it’s prime time for grabbing bonus cash from sportsbooks hungry for your action. With the eyes of the betting world locked in on Pimlico, top betting sites roll out their most aggressive promotions of the year. We’re talking sign-up offers that go well into four figures, reload bonuses tailored for returning bettors, rebates on losses, and even perks for going crypto. These deals aren’t random — they’re timed specifically to help you hit the betting window with extra firepower.

And that extra firepower changes how you play. Instead of tiptoeing around win bets, you can start building exotic tickets — chasing juicy exactas, bold trifectas, or even those massive superfecta payouts. You’ve got more units to spread around, more angles to play, and most importantly, more chances to cash big. We’ve sifted through the clutter and pulled together the promos that are actually worth your time. Here’s where the real value is hiding:

How To Sign Up To The Best Preakness Stakes Racebooks

The Preakness Stakes is fast-paced on the track — and getting your bets in should feel the same way. No drawn-out sign-up process, no confusing instructions, just four simple steps, and you’re ready to fire away on win bets, exactas, trifectas, or whatever else you’re feeling for race day. Here's the step-by-step process:

• Pick your sportsbook: Scroll through our recommended sites above and choose the one that matches your betting style — whether that’s deep promos, early lines, or a slick mobile app. Align with your interests to find the best match.
• Create your account: Signing up is like any other site — just punch in your basic details, verify your age and location, and you’re good to go. 
• Deposit funds: Load up your account with your preferred payment method — cards, crypto, e-wallets, or even bank transfers. Most books offer a range of options (and if they don't, you might want to go elsewhere). 
• Place your Preakness bets: Once your account is funded, hit the racebook, find the Preakness, and build out your betting ticket. From win-place-show to exactas and more, it’s all there waiting. The hardest part is choosing where to allocate your money and what to skip out on.

Sound easy, right? That's because it is. Betting sites design the sign-up process to be as frictionless as possible, and they've largely succeeded at it — so get to it!

Preakness Stakes History

The Preakness Stakes has been run since 1873, and was named after the first-ever stakes winner at Pimlico: Preakness, who won the 1870 Dinner Party Stakes. Though the race was contested in New York for a few years in the late 1800s and early 1900s, it has been run at Pimlico in Baltimore, Maryland for most of its history and has become a major part of Maryland racing lore.

Preakness-Winning Stars

Thirteen Preakness-winning horses need no introduction: from Sir Barton in 1919 through Justify in 2018, through other stars like War Admiral, Citation, and Secretariat, all of the Triple Crown winners have won the Preakness as part of that path.

One of the most interesting storylines of the Preakness Stakes concerns the 1973 victory of the great Secretariat. Although he won the race, there was a malfunction with the electronic timer, and he was awarded a time of 1:54.2, two-fifths of a second off the race record, and the only record he did not break in his Triple Crown campaign. However, for the next 39 years his
connections lobbied the Maryland Racing Commission for a review, and in 2012, the use of modern digital technology, and testimony by those who had hand-timed the race, led to the winning time being changed to a record 1:53, giving Secretariat the record times for all three legs of the Triple Crown, a distinction the big red colt holds to this day.

Man O’ War is another one of the most fascinating Preakness winners. Though some argue Man O’ War rivals Secretariat as the greatest horse in the history of the American turf, Man O’ War bypassed the Kentucky Derby to begin his three-year-old season in the Preakness. He won with authority, turning the tables on Upset (the only horse ever to beat him), and set the stage for an undefeated sophomore season.

Preakness Stakes Betting Tips

As you get ready to bet the Preakness Stakes, there are some things you can keep in mind even before the field for the Preakness Stakes is finalized. That does not happen until after they finish running the Kentucky Derby, but certain historical trends tend to hold year in and year out. Learning those now can give you a head start on Preakness Stakes betting.

Preakness Stakes Odds

Favorites have won the Preakness Stakes about half the time. This is a better strike rate throughout its history than either the Kentucky Derby or the Belmont Stakes. Historically speaking, Preakness winners come into the race off of a good effort, and if the favorite looks like the goods, often they are.

But, favorites have still lost just under half the time across the history of the Preakness. Looking in the first ten years of the points system, more clouds have begun to float over Preakness chalk. In that time, three favorites won the race. The other seven winners were not favored, including two of the ten longest shots in the race’s history, Oxbow and Cloud Computing. In short, if there is a long shot you can make a good argument for, there is value in taking a shot.

Preakness Stakes Pace

There’s a saying in horse racing, the pace makes the race, and that matters in the Preakness Stakes. Though the idea of the “tight Pimlico turns” is a myth, it is true that horses with tactical speed tend to have an advantage in the Preakness. Unless there is enough one-way speed for the pace to fall apart, a horse who does not have too many lengths to close up in the final half-mile is in good position to win.

So, when handicapping the Preakness, look for horses who can sit close to the pace. Unless multiple horses in the field have sharp early speed and need to be forward (which would then set it up for a closer), lean toward those horses with a stalking gear on the win end, and consider the late runners for underneath shares of exactas, trifectas, and superfectas.

Preakness Stakes Connections

Trainers and jockeys who have a proven track record of success in the Preakness know what it takes to prepare their horses for this 1 3/16-mile classic, and prepare them for the raucous crowd that inevitably shows up for the Preakness Stakes.

Among active trainers, none have a better record than Bob Baffert. Baffert has won the second leg of the Triple Crown eight times during his career, most recently in 2023 with National Treasure. That is the most wins in Preakness Stakes history. Other currently active trainers who are always dangerous in the Preakness include D. Wayne Lukas, a six-time winner, and Chad Brown, who has won twice.

Jockeys who have won the Preakness more than once, likewise, may offer an advantage because they have proven that they can coax the best out of multiple horses over Pimlico’s demanding mile and three sixteenths. Among jockeys who are still riding, Kent Desormeaux and Victor Espinoza have won the race three times, while Mike Smith and Javier Castellano have done so twice.