Inside Churchill Downs, From Millionaire’s Row To The Paddock Club

Deep below the 2024-opened Woodford Reserve Paddock Club at Churchill Downs sits a bourbon-stocked speakeasy. It takes a special flick of a latch on a bourbon barrel to even open the door. While this speakeasy is a surprise, it’s also reserved for one of the most exclusive spaces across the entire 175-acre Louisville racetrack and host of the Kentucky Derby. But it’s just one of three private speakeasies across a stadium that likely has more premium seating than any other sporting venue.

Opened with its first race in 1875 and now the longest continuously held sporting event in North America—also one of the largest single-day sporting events in the country—getting to know the unique premium offerings throughout Churchill Downs can be a lifetime endeavor.

Mike Anderson, Churchill Downs Racetrack president, tells me he sees a socio-economic cycle occur at the Derby, with college-age fans attending the infield and then slowly moving up in premium amenity seating as they age, always aspiring for the next amenity level. “As you progress in your profession, you move to that next section,” he says. “You want to go higher, see the whole track.”

But just where can you go? Each different space features a different amenity level. And a different price point. “What is your experience quest you want to be on?” Anderson asks. Following a major overhaul that was ready for 2024, which included restoring the paddock back to its former glory, projects continue throughout the site. Let’s explore a few of the must-know areas at Churchill Downs.

Spires Terrace And Suites

Thanks to a bold move by a 24-year-old draftsman when Churchill Downs added its brick building in 1895, the Derby’s home has twin spires, two hexagonal spires that rise as the prominent backdrop of the Derby grandstand. The 2024-ready renovations ahead of the 150^th running of the race helped make the spires more visible.

The 2024-opened Spires Terrace and Suites—at somewhere between $15,000 to $17,000 per seat for a two-day ticket, Sarah Contardo, Churchill Downs senior vice president of sales and strategy, tells me—created outdoor luxury dining with a personal concierge for each guest. Situated under the iconic spires, the terrace has a rare 360-degree view of both the newly revamped paddock and the racetrack.

The Mansion

This is the most expensive ticket at the Kentucky Derby ($22,000 face value) and the most private location on site. When opened in 2013 it was named The Mansion since it was designed to look like a southern mansion with expansive rooms (whether you agree with the interpretation is up to you).

Elevated over the finish line, The Mansion is about privacy and extravagance for the under 300 guests. Entry is through a nondescript wooden door amidst more general ticket holders, but the space is meant to impress with two show kitchens, made-to-order food all day and incredible views of the track.

Woodford Reserve Paddock Club

Considered the second-most premium ticket at the Derby, Contardo says, the Woodford Reserve Paddock Club opened in 2024 for 500 people. The club sits on the ground floor with views into the backside of the paddock and the walkway tunnel the horses take to move between the paddock and the track.

Guests enjoy those views, prime seats near the finish line and plenty of personal concierge services, including high-end amenities on race day. The area features a bourbon room and when guests go downstairs, they go past the secret speakeasy through a bourbon rickhouse tunnel and emerge into the paddock itself.

The Paddock opened new 2024 and cleared room for fresh views of the twin spires. Depressing the paddock ring up to eight feet below grade allowed for more seating and more views of the horses and the jockeys meeting before the start of the race. “It is where you want to be seen, celebrities want to be inside that circle,” Anderson says. “It is the heartbeat of the track there and we expanded and opened that up.”

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Oaks And Kentucky Derby Suites

On the track-facing side of the Woodford Reserve Paddock Club are the special near ground-level suites reserved for the owners of the horses running in the Oaks and the Derby. The owners have their own special seating, but also access those seats through the Paddock Club.

Club SI

A mirror of the Paddock Club situated on the other side of the walkway tunnel the horses take, this club doesn’t have quite the level of amenities as the Paddock Club, but with all the same views. Still, this is no space to scoff at, with plenty of special touches reserved for guests.

Homestretch Club

The Jockey Club and the Homestretch Club are two of the premium spaces situated between the Clubhouse and the starting gate. What gives the suites and terraces a special touch in the Homestretch Club is that it features the longest bar in Kentucky. There is also seating that brings guests right up against the track.

Turf Club

Opened in 2016 with an expanded balcony, the Turf Club is where up to 60% of celebrities sit. With seating along the main homestretch on the frontside of the track, the club amenities fall behind the seating.

Whether presidents, the Queen of England (Queen Elizabeth II attended five race) or the modern-day celebrities, Anderson admits it is important for celebrities of all walks of life to attend the race and create buzz for the event, helping draw new generations of fans to the Kentucky Derby. “It brings an excitement level for a new generation of customers,” he says.

Millionaires Row

Located on the fourth floor of the Clubhouse and overlooking the finish line, this is a classic area for the Kentucky Derby. This club holds 850 people with balcony viewing of the track near the finish line, but despite its name it is no longer one of the most exclusive at the Kentucky Derby.

Matt Winn’s

Named after a former president of the track from the early 1900s that helped bring Churchill Downs into national prominence, the 320-person club along the main clubhouse space has a steakhouse feel.

Room 20

You can’t even buy a ticket to Room 20. One of the three speakeasies on the property, this is an invite-only room near Matt Winn’s—Winn had a similar room he’d bring prominent guests to in the early 1900s—that is still reserved for those with a special connection.

Stakes Room

Built in 2016, this is a space dedicated to the horses of the Kentucky Derby. With an over-the-top bar shaped like the oval track as the central point of the space, the seats are near the finish line along the homestretch of the track.

Skye Terrace

One of the oldest clubs at the track—it is scheduled for demolition and a complete rebuild—this 450-person club from the 1950s still boasts excellent views near the start of the first turn.

Anderson says that with dozens of premium spaces at the track, guests will often bounce around locations from year to year to create new experiences for themselves. “People appreciate that they can find what they want here,” he says. “We do have so many different levels. They can be private, public, see celebrities, see the horses.”

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