I visited Keeneland in the fall for the last weekend of their Fall Meet last year. I’ve been to steeplechase races in Virginia, including Gold Cup, but this was the first flat race around a track that I’d been to. I prefer a fall horse race for so many reasons, and this was a fun one to add to the list. If we’d had more time in Lexington, this would have been a great weekend activity to pair with exploring some of the bourbon trail.
Travel Diary: How We Ended Up at Keeneland In the Fall
Coming from DC with no connection to Kentucky, how’d we end up Keeneland? Well, we have good friends who live in Nashville, and we love going out there to visit them. They also happen to be people who love to travel and explore and, when we planned a fall trip, they suggested we take a two-night excursion to Lexington. One of them had been there many times for work, but hadn’t had the opportunity to check out Keeneland. We were obviously game.
We actually flew into Nashville just to make the round trip flight easier, and our friends picked us up from the airport for the 3-hour drive. We rented the most darling Airbnb, an old home with original wood floors, and decked out in horse decor and antiques. It was the perfect home base for a quick 36 hours in Lexington.
What to Expect on a Fall Afternoon at Keeneland
The track was a quick drive from the house, and we were able to get there early to tailgate at our car before going in. We brought some drinks and snacks, but the scene was definitely quiet given the weather. We chatted with a group next to us, 8 guys who told us they make the trip every year. They were casually drinking and catching up, and providing us with prime people watching.
One of the reasons I love a fall horse race is the laid-back vibe, and this fit the bill. There was no rush to get anywhere. Want to have another glass of bourbon at the car? Sure, let’s hang out here for a little while longer. There wasn’t the sense that we were missing anyone or anything (though, perhaps, that’s also the advantage of going somewhere where you don’t know anyone else).
Once we finally made out way in, the guys headed straight to place their bets. I wish I could say we won big that way, but luckily we just paid a small price for the excitement of being invested in the races. We bought $15 grandstand tickets so that we’d have a seat and, given the off and on rain we had throughout the day, those extra few dollars were well worth it (plus, $15 seemed like a deal!). As the rain came and went, we alternated between going up to the track for a front row view and taking cover under the grandstand.
We made sure to indulge in plenty of Kentucky bourbon and Keeneland’s delicacy, Burgoo, a warm stew of meat, vegetables, and potatoes. No surprise, I grabbed a hot dog to go with it. The best of sports eating, right?
Thanks to cheap tickets, we didn’t feel pressure to stay all day — again, back to that laid-back vibe. We hung out for long enough to see the sights, enjoy a day at the races, and then headed back to the warmth of our Airbnb before a night on the town in Lexington.
What to Wear to Keeneland In the Fall
Okay, the biggest question…what do you wear to Keeneland in the fall?
You’re going to see all sorts, as you would at any fall outdoor event. When we went last year, we had a cool, dreary fall day. Sure, a crisp, sunny day would have been great, but you need those gray days to welcome in the season. For Keeneland in the fall, we would have been dressed for the occasion in more casual pants if we’d wanted, though I always prefer to get a bit more dressed up — within reason. I like to use horsey events as an excuse to bring out those dresses and skirts that are a little too formal for everyday, a little too outdoorsy for work, but a little too casual for evening. It’s a very specific niche.
I wore an old — perhaps a decade or more old — Elizabeth McKay dress in a brown and ivory shirting stripe with brown tights, brown riding boots, a quilted Barbour jacket, an Hermès pheasant scarf, and a Longchamp bag. While I’m rarely without a hat, this day felt too drizzly to even bother.
And, if you need a bit more inspiration, I rounded up a few ideas here.