There are few things as wonderful as an October weekend in Lexington, Kentucky, with beautiful weather, horse racing, SEC football, and plenty of bourbon. You have probably gathered by now that we love bourbon, but what you may not know is that I (Angela) went to the University of Kentucky for undergrad. For all you sports fans, that means I am not fun to be around during basketball season. But that also means I have a unique perspective on all the best things to do in Lexington, and when to do them. Over the past few years, we have nailed down a strategic timeline of our visits to Lexington each year. We make the trip in October, January, and April – and we will be highlighting our October trip in this post.
Lexington Basics
Getting There
For us, Lexington is a 5 hour drive directly south on I-75, an easy drive for a weekend trip! Lexington is located about an hour south of Cincinnati, 3 hours from Nashville, and about 5.5 hours from both Atlanta and Chicago.
Where to Stay
We should mention here that we are very loyal to Marriott (which pays huge dividends for us as we travel). Lexington gets very busy in October, so it is important to book early, but there is something for someone at every price point in the area. Even within the Marriott network, there can be a $200 per night swing depending on the exact location. If you want to be close to the action (which, if it is in your budget, we do think is worth it), you will have to pay a premium. If you are on a tighter budget, you will not be missing out! You just need to be willing to spend a little more time traveling between your hotel and the activities.
If we were traveling in a group, we would likely seek out a rental property. When we go to Lexington, we usually stay in one of 3 hotels since many of the people we spend time with while we are there are local.
Fairfield Inn & Suites Lexington North
- Pros: budget-friendly, near I-75, free breakfast, clean and quiet, free parking
- Cons: 10-15 minute drive/Uber to most attractions, including downtown
Springhill suites Lexington near the university of kentucky
- Pros: walking distance to football stadium (a long walk, but great for avoiding game day traffic), short drive/Uber to downtown and other attractions, free breakfast and lots of food options very close, free parking
- Cons: usually the most expensive of these three options during football season, not walking distance to everything
lexington marriott city center
- Pros: directly on top of some of the best restaurants and bars in the city, walking distance to the stadium, brand new hotel (2020) and quite luxurious
- Cons: fairly pricey, no free parking, no free breakfast
Getting Around
The bourbon portion of your October trip to Lexington will only include one distillery, but this is the tip of the iceberg when it comes to bourbon. This post is going to highlight a full day at Keeneland, starting with tailgating – which will require you to bring your vehicle and assign a designated driver. Your best bet on game day is going to be to walk if at all possible, otherwise, we highly recommend that you don’t drive. Let someone else do that for you, especially if you plan to tailgate.
Suggested Itinerary for Your October Weekend in Lexington
Thursday – Arrival In Lexington
Welcome to Kentucky – arrive in Lexington and settle in to your hotel. Grab a drink at the nearest bar, and it darn well better be something with bourbon!
Friday – Bourbon and Horses
Today is for the horses! You will need to be ready for the day around 9am. There are a million opinions on what to wear to Keeneland and you will surely see the full spectrum, but there really isn’t a strict dress code (as long as you are not in the Clubhouse). Check the weather – October in Lexington can be 80 and sunny or 40 and rainy. Typically, Ray wears khakis and a button-up and I wear a maxi dress.
Eat a hearty breakfast because today is going to be a busy day. After breakfast, you will need to stop at Liquor Barn to stock up on all the essentials for Keeneland. We recommend Maker’s Mark, Ale-8-One, beer cheese dip and pretzels, and any other hearty tailgate snacks.
Woodford Reserve
Your first official stop will be at Woodford Reserve Distillery around 10am – you will need to book your tour in advance. Even if you don’t drink, Woodford Reserve is a beautiful and historic place every Kentucky visitor should experience. If you’re like us, you won’t be able to leave without buying a bottle of bourbon. We recommend Woodford Double Oaked.
Keeneland Race Track
Woodford Reserve is located within a convenient proximity of Keeneland race track, so when you are done at the distillery, head to the races! Make sure to stop at Doughdaddy’s to pick up a dozen doughnuts the way. There will be traffic, but you will soon see the vast expanse of the Keeneland tailgate scene as you are directed to a parking spot. Pop your trunk, and enjoy the atmosphere. People are very friendly, so who knows, you may even make some new friends!
We recommend you buy your tickets for Keeneland in advance for the best experience. The first post (race) is usually at 1pm, but depending on how much fun your are having tailgating and how much you would like to gamble, it is up to you to decide when you would like to enter the track. The races last all afternoon, and there are plenty of food and drink specialty items to try, but we highly recommend the Burgoo (a hearty stew of meat, veggies, and potatoes).
After the races, it’s time for dinner. There are so many incredible dinner options in Lexington, and we recommend that you make reservations for your group wherever you decide to eat.
Saturday – Football
Good morning football fans and Happy Caturday! Grab some coffee from a local coffee shop, and maybe a doughnut from one of Lexington’s famous bakeries. Depending on the time of the game, and whether or not you decide to attend the game, you have a few options for today. If you have never been to an SEC football game, don’t miss the opportunity! We recommend that you start out by getting brunch at The Local Taco – breakfast tacos, mimosas, and right on campus. Spend some time walking around the tailgates and enjoying Kentucky Football’s vibrant and exciting atmosphere.
Cheer on the Wildcats either at Kroger Field, or from a nearby bar. KSBar is a great place to watch Kentucky sports, but if you want to go here, you will need to skip tailgating to get a seat. For the party crowd, Tin Roof’s Parking Lot Tailgate is a great time – and you will be able to watch the game on a big screen there.
Today is a good day to keep the party going by checking out a local brewery or two before dinner. We love to get pizza for dinner on game days, and we highly recommend heading over to the Distillery District to Goodfellas Pizzeria. The Distillery District is home to plenty of attractions to enjoy before or after dinner, including Etherial Brewing, Crank and Boom Ice Cream, and James E. Pepper Distillery.
Sunday – Heading Home
Your October weekend in Lexington is coming to an end – grab brunch at Carson’s before hitting the road.
Until Next Time
There is so much more to Kentucky than we were able to go through in just one post, but we have done this itinerary over and over again and it never gets old! We really encourage you to put Kentucky on your list of places to visit, and to consider taking an October trip to Lexington. There are endless things to do and see, great eats and drinks, awesome music, and that’s why this is one of our favorite cities in the US.