Driving down Gandy Boulevard, you can’t miss it. That massive, slightly weathered sign for Derby Lane still looms over the St. Pete landscape like a concrete ghost. For nearly a century, this was the cathedral of greyhound racing. Now? It’s called Win! Derby, and honestly, the vibe has shifted in a way that most locals are still trying to wrap their heads around.
If you’re looking to win derby at historic Derby Lane St Petersburg, you aren’t betting on the "Hareson Hare" lure anymore. Those days ended on December 27, 2020, when the last greyhound crossed the finish line due to Florida’s Amendment 13. But the lights are still on. The parking lot is still packed. Only now, the action has moved from the dirt track to the felt of the poker tables and the high-def glow of simulcast screens.
It’s a weirdly beautiful transition. You’ve got this 130-acre relic of Old Florida—the same place where Babe Ruth and Lou Gehrig used to hang out during spring training—slowly morphing into a massive community hub.
The New Game: How to Win at the Poker Room
The heart of the operation is the Win! Derby Poker Room. It’s one of the largest in the state, and let’s be real, it’s where the actual money moves these days. They aren't just running a few tables in the corner. We’re talking over 50 tables of live action.
If you want to walk out with more than you brought, you need to understand the local "ecosystem." Unlike the flashy, tourist-heavy rooms in Vegas, the crowd here is a mix of seasoned "grinders" who have been playing in St. Pete for decades and casual fish coming in for the weekend promotions.
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- The Promotional Cycle: This is key. In January 2026, they’ve been running some wild stuff. We’re talking "$2,026 Grab Bags" every 30 minutes on Wednesdays and Thursdays.
- High Hand Frenzy: On Saturdays, they often run "Insta-Pays" where high hands can net you $500, $200, or $100 on the spot.
- The Prime Perk: If you’re a regular, they have "Prime NLHE" rewards. Play 30 hours of $1-$3, and they basically hand you $300 back. It’s a volume game.
The tables feature everything from Texas Hold’em to Three Card Poker and Mississippi Stud. If you’re a beginner, go during the day on a Tuesday. The vibe is chill, and the dealers are usually happy to help you navigate the betting structure of games like Ultimate Texas Hold’em (UTH) or Pai Gow.
Why the "Historic" Part Still Matters
You can feel the history the second you walk into the Derby Club on the 4th floor. It’s got that "Circa 1925" energy because, well, that’s when T.L. Weaver first opened the place. It’s arguably the oldest continuously operating site of its kind in the world.
There’s something surreal about sitting in tiered seating, watching a thoroughbred race from New York or a greyhound heat from West Virginia on a massive screen, knowing that the very ground you’re sitting on once hosted the legendary dog Keefer in front of nearly 13,000 screaming fans in 1986.
The simulcast area is now located on the 6th floor. It’s been totally renovated with a full bar and individual flat-screens. It’s the closest thing you can get to the "old way" of winning at the derby, just through a digital window.
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It’s More Than Just Gambling Now
Here is what’s actually surprising: Win! Derby has become the new home for the spirit of the old Wagon Wheel Flea Market.
Since late 2025, the parking lots have been hosting the Farmers and Flea Bazaar every weekend from 7:00 AM to 1:00 PM. It’s basically a massive party with 150 vendors, food trucks, and people hunting for antiques. Sagi Genger, the CEO of Rally Development (the firm that bought the site in April 2025), is leaning hard into this community-centric model.
They’ve also started hosting massive cultural events. In August, an Asian Mega Night Market brought in nearly 18,000 people. Think about that. That’s more than the track’s record attendance for actual racing.
The Future: Will the Rays Move In?
The big elephant in the room is the redevelopment. This is 131.5 acres of prime real estate in a metropolitan area. That almost never happens.
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Rally Development is currently marketing the property through Berkadia. There is constant chatter about whether this will become a "multi-billion-dollar" entertainment district or even the new home for the Tampa Bay Rays. While nothing is set in stone as of early 2026, the owners are expected to reach a conclusion on the site’s permanent future by March.
For now, the gaming business stays. It’s too profitable to shut down, attracting roughly 16,000 people a week.
Actionable Tips for Your Visit
If you’re planning to head over to 10490 Gandy Blvd, here’s how to do it right:
- Check the Calendar First: Don't just show up. Their website (win-derby.com) lists specific tournament guarantees. Some weekends have $100,000 guaranteed prize pools that bring in pros from all over the country.
- Use the Rewards Card: Join the Win! Derby Rewards program immediately. It’s free, and the food/drink comps add up fast, especially if you’re playing the "Prime" tables.
- Simulcast Strategy: If you're there for the races, the 6th floor is the spot. It's quieter, the view of Tampa Bay is actually decent, and the betting windows are more accessible.
- The Bazaar Experience: If you’re bringing family, go Saturday morning for the Flea Bazaar, then grab lunch at the Derby Club 4 buffet. It’s the best way to see the "whole" property without just sitting at a poker table for eight hours.
The "win" at Derby Lane isn't always about the jackpot. Sometimes it’s just about being part of a century-long tradition that refuse to die. Whether you're chasing a Royal Flush or just a good deal on some local honey at the market, the place still has that weird, infectious energy that only St. Pete can provide.
Keep an eye on the news through February 2026. The shift from a historic track to a modern entertainment "placemaking" project is about to hit high gear, and you’ll want to see this version of it before the cranes inevitably move in.