Kentucky in the fall… What a glorious time and place to experience crisp mornings, changing colors of leaves, and warm, salted caramel lattes (or your beverage of choice) while also gearing up for a day of fun and exploration.

Let’s get right to my top recommendations for things to do in Kentucky in the fall.

Keeneland Race Track – A Day at the Races

The Keeneland fall meet is open the first Friday through the last Saturday in October. (Check for specific dates.)

Keeneland Racetrack Lexington Kentucky in the Fall

If anyone wishes to visit Kentucky, and they aren’t picky about when, I always recommend that they come in October or April so that they can take in a day at the races. Keeneland has offered its guests world-class horse racing for more than eighty years. And it is clear when you spend the day at this particular track that Keeneland has perfected the southern hospitality they are known for.

Things not to miss while at Keeneland: the Keeneland Shop (gift shop), roaming around the paddock between races, and of course the races.

Food and drink not to miss while you’re at Keeneland: spicy Bloody Marys, a bowl of homemade Kentucky burgoo, and Keeneland bread pudding with bourbon sauce.

Bonus Tip: If you can fit it in your schedule, check out the morning workouts on the main track, where you can see horse trainers and jockeys working with the horses on the main track or on Keeneland’s practice track. After, stop by the Track Kitchen for breakfast. You just might find yourself having breakfast next to a notable owner, trainer or jockey.

Riders on their morning workout at Keeneland racetrack

I was just at Keeneland yesterday at 7:30 am—just in time for a beautiful sunrise and to catch the second wave of riders and thoroughbreds getting their morning workouts in.

The Bourbon Trail

You can of course visit any stop along the Bourbon Trail any time of year, and it’s always a good time.

However, fall in Kentucky is the perfect time to schedule a visit to Woodford Reserve (a traditional favorite among bourbon lovers) or Castle & Key (a newer addition to the Bourbon Trail).

Heather and Mike Sunseri at Castle & Key Bourbon Distillery on the Bourbon Trail in Woodford County Kentucky

Or… since these two bourbon distilleries are only about a mile apart, schedule both stops in one day. Because if I had to choose just one for you to visit, I wouldn’t be able to. They both offer such unique experiences that I think you need to visit both.

As a third choice, in case you’ve already experienced Woodford Reserve and Castle & Key, I recommend a short drive over to Frankfort. There you will find a beautiful distillery to visit in the fall (or anytime)—Buffalo Trace.

Buffalo Trace’s bourbon tour is drenched in history and laced with time-honoring tradition.

Side note: Buffalo Trace’s grounds were the inspiration for the fictional distillery I created in the thriller I wrote set in Kentucky: Exposed in Darkness.

SEC Football

Kroger Field SEC Football University of Kentucky Commonwealth Stadium

I almost ended this section with the heading and a picture. What more is there to say?

But just in case you’re not from around here, and because I love introducing people to experiences they’re missing out on in their lives…

There is nothing like a crisp fall afternoon of two rival SEC football teams knocking shoulder pads. Of course, that’s only part of the thrill.

Tailgating is what it’s all about in the South. And I will argue with anyone out there until I’m on my death bed that no one tailgates like SEC fans.

This, of course, is coming from a Kentucky girl. (My Oregon Duck husband probably has something to say about this.)

While UK doesn’t always excel at football, put us up against any one of our SEC rivals, and we will do our best to put up a fight. And no matter the point spread for the day, we will ALWAYS throw a nice party before the game—rain, snow, or shine.

Hike the Red River Gorge or Visit Natural Bridge State Resort Park

There is no better place to take in the gorgeous fall foliage or to simply experience the crisp mornings that fall in Kentucky offers than in the Daniel Boone National Forest.

Red River Gorge fall foliage Kentucky in the fall

You can take a short trail to the get a view of the “Natural Bridge,” the most famous sandstone arch in Kentucky.

Or if you want fewer crowds and get in more of a workout with your hike, you can find a loop or trail in the Red River Gorge. There you will see even more views of brilliant arches and rock formations. And in the fall? You will see the most gorgeous expanse of colors in the foliage.

ALSO READ: Hike and a Pint: Rough Trail at Red River Gorge

Fall Festivals and October Fests

I simply adore Kentucky small towns in the fall.

I don’t know what it is. Maybe it’s the shift in excitement that comes with the cooler temperatures. Maybe it’s the enthusiasm from little shop owners because of the impending holiday season. I swear people have an extra spring in their step when they start decorating with witches and bats.

And when it comes time to change things over to snowmen and candy canes? Watch out!

And what better way to get a true small town feeling than with a fall festival? Just do a simple Google search for any town in Kentucky and you will find that most of them have some sort of fall festival or Octoberfest.

I love exploring small towns I visit rarely, grabbing lunch or an afternoon snack from a street vendor. Caramel apples anyone?

Kentucky in the Fall—No Shortage of Things to Do

Someone recently asked me where I would send someone in Kentucky if they’d never visited.

The above list is filled with experiences you can get almost any time of year. But Kentucky in the fall? I would do my absolute best to fit every item on the list into a single weekend.

Okay… a really long weekend.