“I personally like the experience of seeing all those people packed in like sardines, cheering for their horse at the same time, the grandstand pulsing with excited energy for the 90 seconds their swift hooves churn up the track dirt.”

—Kristin Luna

Bourbon and horses. Horses and bourbon. These are two industries that anchor Lexington, bringing hundreds of thousands of visitors—myself included—to this charming, mid-size Kentucky city year after year, but particularly during Keeneland when you can enjoy the best of both from the comfort of the sprawling racetrack grandstand.

It’s funny to think that two years ago I’d never been to Lexington; now, I’ve visited four times in the past 18 months and would venture to say it’s one of my favorite Southern cities, completely underrated and full of culture, sass and charm. And though Churchill Downs may be the more well-known of the tracks, Keeneland is every bit as steeped in tradition with a history dating back 80 years.

On my first trip to Keeneland last April, it rained so hard that Old Frankfort Pike flooded, and not only could we not drive out through Horse Country to see the farms, but we couldn’t even do what we do best on rainy days: drink bourbon at Woodford. This visit, however, couldn’t have been more different: early autumn posing as summer, a sweaty 90 degrees and not a cloud in the sky.

It was perfect, exactly what you hope your every day at the races might be.


Keeneland’s season happens twice a year: in the spring (April) and in the fall (October). We went on opening day both times, a Friday, so as you can imagine, it was more than a little crowded. I personally like the experience of seeing all those people packed in like sardines, cheering for their horse at the same time, the grandstand pulsing with excited energy for the 90 seconds their swift hooves churn up the track dirt.

For the crowd-adverse, mid-week is a great time to get your fill of racing as the event runs every Wednesday through Sunday for four weekends straight every October and again in April.

But before you even get to the track, it’s best you learn a bit about how the industry works first, wouldn’t you agree? As horse racing becomes more and more mainstream, so do the neighboring horse farms, opening up their operations for tourists to enjoy.

Last year, we took a tour of WinStar Farm in Versailles; this time around, it was Taylor Made in Nicholasville, which is billed as a sales agency and boarding facility for thoroughbreds. We visited the foaling quarters, the paddock, and the yearling division where the horses transition from weanlings to yearlings.

Not growing up in the horse world, I found so much of it fascinating, such as how they separate the younguns into different paddocks by girls and boys—it’s like the horse version of a high school dance—and how a stallion can have up to three, ahem, dates with different mares per day.

Taylor Made also happens to be the former home of last year’s Triple Crown and Breeders’ Cup winner American Pharaoh, so we got to meet a few of his children.

This 1,100-acre farm nearly occupies its own zip code, so you’ll use your car to drive between facilities and learn about the whole process from breeding to showing the horses to future clients.

Racing veteran or track newbie, it doesn’t matter, a Lexington area horse farm tour is an activity that will both educate and entertain anyone passing through northern Kentucky.


The Backstory of Keeneland

Born in 1936, Keeneland was founded in the middle of the Great Depression as a non-profit and community venture with the intention to create a track unique in structure and bring racing back to Lexington. The team behind it succeeded spectacularly as Keeneland is now a National Historic Landmark and considered the major prep races for the Derby, which takes place the following month, not to mention an annual tradition for so many Kentuckians.


What to Wear to the Races

Literally, anything goes at Keeneland. Well, OK, maybe not anything, but I saw everything from Hawaiian shirts to full-on three-piece suits. It’s definitely not as fancy, clothing-wise as Derby is.

If you’re a guy, nice slacks and a button-down shirt is always a good choice. Some men dress a little more, shall we say, flamboyantly than others, like my color-loving husband. If you’re more of a dapper dresser, don’t be shy busting out the sport coat and tie like these handsome gents.

The ladies seem to mostly dress in what I would consider Southern “game day” apparel: tasteful sundresses and cute flats or boots, or a skirt and nice top. One thing I’d advise is leaving the heels at home—trust me, gals, you do not want to be traipsing about the Paddock in stilettos!

Do I Need a Hat?

Well, no. Though it’s a lot of fun to try and find one!

Truth be told, the first time I came to Keeneland, I borrowed a handful of hats from my Kentucky pal Beth but didn’t wind up wearing them once I saw very few women in them. Still, anything goes, and if you’ve got a hat of your own, I fully encourage you to bust it out and wear that beauty proudly!

For those who get the opportunity to visit the clubhouse, as we did our first Keeneland in spring of 2015, you’ll be required to dress fancy, with men in a coat and women in dresses, tailored pantsuits or dress slacks.


Don’t Miss the Paddock

Between races, you’ll find crowds congregating in the central paddock area. This is not only a great meeting place if you’re doing the races with a group, but it’s also prime horse-watching, as the thoroughbreds are led out and paraded through the grassy fields before they take to the track.

It’s also great people-watching, as you’ll see many of the horse farm owners, the millionaires behind the industry and the petite jockeys themselves, who are akin to Hollywood stars within their racing world.

How to Bet

While I’m no gambler—I’d rather spend that cold, hard cash at the bar!—my husband put his money on a few horses (and lost, oops). You can head to any one of the betting counters where they’ll get you all set up, or you can read up in advance on how to do it.

There’s also an app for that, unsurprisingly, so the lazy better needn’t even leave his seat to stake his claim.

Getting to the Track

You’ll want a designated driver, obviously, as having a cocktail is often a part of joining in on the race day crowds. The track itself is just 10 minutes from downtown Lexington; once there, you can pay to park close by or do the free parking option, as we did, then take the free shuttle to the entrance.

If you want a traditional Lexington hotel, look no further than the historic Gratz Park Inn, which sits on land that was settled in 1781. You’ll really feel the pomp and circumstance of the horse industry as you sip your bourbon (neat, naturally) down in the opulent library where you’ll feel the need to sport a smoking jacket and light up a fat cigar, even if you don’t smoke.

If you’re looking for something a bit more modern, the brand new 21c Museum Hotel has been getting rave reviews. While it was booked solid during our visit, I’ve stayed at the Louisville property, and it’s a fantastic boutique option for those who love design hotels.

What Keeneland Costs

Grandstand admission: $5

Parking: free

Draft beer: $7

Premium beer: $9

Cocktails: $10 to $15

A lunch plate: $10

Are you convinced to give horse racing the old college try? Will you join me for opening day of Keeneland next spring? See more of Kristin’s photos here.