The Game Day No One Knows About
Keeneland race track
“Horse races are a passion of mine. It’s not about the betting. I hate gambling. I’m likely the most risk-averse person on the planet. But you go there, smoke a few cigars, drink some bourbon, tailgate all day, and put $2 on a horse so you can yell something - that’s what it’s all about.”
This post contains excerpts from an interview with Scott Underwood.
Introducing Scott:
Scott is a native Kentuckian, now living in Atlanta. When we saw the captivating recommendations he made for a horse race named Keeneland we were super-intrigued and just had to find out more! So we interviewed him.
Keeneland in Lexington, Kentucky is apparently home to two big races. The first races are held in April and the next batch of races are held in October. Scott makes it a point to go at least one weekend a year. He drives up from Atlanta on a Friday and drives back on a Sunday.
He was kind enough to answer some questions for us and guide us through a weekend at Keeneland. In essence, it’s an event for grown-ups to relive the debauchery from college game-days.
When did you start going to Keeneland?
Growing up in Owensboro, KY, I was raised around horse races. It started with the Kentucky Derby and Oaks when I was younger. Later, I started going to Keeneland throughout high school and during college at Western Kentucky University. There were other race tracks nearby but no one went. For example, the Kentucky Downs was only 20 minutes away from college but there was no history there, no atmosphere and thus no reason to go. It wasn’t as cool. Twice a year though we’d drive all the way down to Lexington to go to see the races at Keeneland instead.
As soon as you step foot into Keeneland you get chills. It’s a completely different atmosphere from other races. When you step foot inside, you see the old brick buildings, the clock towers and the hedges flanking the tote board. It’s truly one of the few racing facilities that’s retained its historical integrity.
What do you do when you get there?
Friday, Day 1
6 AM - 1 PM: Drive from Atlanta to Lexington
On the drive up from Atlanta you hit Versailles Road which is a long stretch of picturesque countryside houses, rolling green hills and white picket fences. It’s super cool and adds to the overall atmosphere.
2 PM - 7 PM: Go to Bardestown & do the Bourbon Trail
Once you get into Lexington, you’ve got every good bourbon distillery in the world within driving distance. Authentic bourbon is only made in Kentucky and most of it is made in Bardestown. Bardestown is the big one - the mecca of all badass bourbons. All the bourbons you’ll see there, you won’t find anywhere else. Bardestown is about 30 minutes away from Lexington and they do this Bourbon Trail which is fantastic. It’s a tour of the six big distilleries in town: Maker’s Mark, Wild Turkey, Woodford Reserve, Jim Bean, Heaven Hill and Four Roses. But that’s not the half of it - there are many other smaller bourbon distilleries in town, and they’re all are gems - each with their own story to tell.
Kentucky Bourbon Trail Passport
Pappy Van Winkle is the best bourbon on the planet. You can’t find it anywhere else. They only make about 7,000 cases a year. Even in Atlanta which is only six hours away - you’d be lucky to find a drop there. But in Kentucky, especially Bardestown, you can get it at the liquor stores by the bottle. Another bourbon at the top of my list is Elmer T. Lee. It’s very very smooth and is a little more full than a Basil Hayden or an Eagle Rare. Highly recommend trying both if you’re in the area.
Pappy Van Winkle Elmer T. Lee 
8 PM - Late: Dinner & drink in Lexington
Once we’re done with the Bourbon Trail it’s back to Lexington for dinner and a night out. Two fantastic restaurants I always go to are Ramsey’s and Malone’s.
Ramsey’s Malone’s
Ramsey’s is an awesome southern restaurant with character. There are four locations but the original Ramsey’s on E. High St. is the best. They have 3 for 1 drink specials for starters - I’ve never seen that anywhere else. On top of that, when a fire truck rolls by with sirens on everyone gets a free drink. If you want to tuck in though go to Malone’s - the best steakhouse in Lexington.
Saturday, Day 2
9 AM - 2 PM: Hit the tracks & tailgate
Saturday we get dressed up. Keeneland is a Bonobos fucking runway show. You’ll probably see guys wearing those hideous red pants but that’s part of the fun. Guys - blazer and bow tie . Ladies - sun dress and big hat.
Next we do breakfast downtown, throw in a mimosa and bloody mary round to get the day started and then we get to the track. That’s when the fun begins and we tailgate for a few hours beside the track and play some corn hole.
2 PM - 8 PM: Grandstand!
Admission tickets to get into Keeneland are about $5 per person. This is definitely not like the Kentucky Derby where they charge upwards of $40 for a ticket. Once we get our tickets and move in, it’s all about having a good time.
The races start at about about about 3-4 PM. We usually find a spot in the back, chill and watch races for the rest of the day. Basically we’re there to drink and have a good time so I always place low bets. I never bet more than $2 or $3 on a horse. I’m not going there to lose $200 - $300. It’s not about the betting. You go there to smoke a few cigars, drink some bourbon, tailgate all day, and put $2 on a horse so you can yell something - that’s what it’s all about.
8 PM - Late: Downtown Lexington
After the track, Nick Ryan’s Saloon is a perfect spot for dinner. It’s is in a part of town that’s quintessentially southern. In some cracks of the pavement you can still see the old brick street and the building itself looks like it’s straight out of the 19th century. When you walk in there’s a bar (with awesome bourbon selections). The menu here is unbelievable. The shrimp and grits (chopped up w/ andouille sausage in them) is fantastic. The Southern cob salad is also very very good.
Nick Ryan’s Saloon
For drinks, Bigg Blue Martini in the downtown Hilton lounge is a great place to start the night. Usually follow that up with drinks at one Sky Bar - my favorite bar in Lexington. Right around Sky Bar are tons of other great bars to hit up as well. Downtown is where you want to stay when you go to Lexington so you can go out at night.
Bigg Blue Martini Sky Bar
Sunday, Day 3
10 AM - Late night: Tailgate @ Louiseville Parking Lot
You really understand the breadth of the amount of people there when you’re tailgating. They open up the farms when the races are on so as your eyes scan across the landscape, thousands of cars cover the hills. It’s unbelievable. If you’re lucky enough to get a spot in the Louisville lot - that’s when you can hang out right by the track. That’s why we usually do that on Sundays because it’s too damn hard to get there on Saturdays with the crowds. That’s where you want to be though when you’re tailgating. It’s a perfect spot.
We had excellent positioning. This is on the side of the track where no one really spends a lot of time because everybody wants to get inside to place bets and drink. This is good for Sundays when you want to take it easy. This picture is cool though because I’m right on the rail. It’s unbelievable seeing the horses up close like that. It’s a different way to experience the races.
Why do you go back every year?
Keeneland is truly unique and represents what Kentucky’s all about. There are other race tracks. Louiseville is only 60 miles away from Lexington and if you get too bored you can go there but it takes the Kentucky spirit out of it. Anything we have that’s worth a damn is horses, bourbon and Keeneland.
