Our Weekend Getaway to Kentucky

Two years ago for Jody’s birthday, I started to plan a surprise trip to Kentucky for a weekend on the Bourbon Trail. Our schedules, however, weren’t flexible enough to make that trip work (we instead spent the weekend in Charlottesville, Virginia – you can read about that here!), so we postponed it for his 30th birthday, which was just two weeks ago! So, this past weekend, we packed up Shelby, my affectionally named Subaru, for a road trip to the Bourbon Capital of the World.

Kentucky was an absolute dream – we had the best time and did so much in our short weekend there. Since we drove, we chose Lexington as our home base, which I would do a thousand times over. It was a little city, similar to Richmond, but still had a ton to offer. For today’s recap, I thought I’d share what we did, sorted by the type of activity that it was. Kentucky has so much to offer and there’s even more that we didn’t have a chance to do, but these are things you definitely want to consider, if you are ever thinking of visiting.

The Bourbon Trail

In case you didn’t know, Kentucky produces 95% of the world’s bourbon, hence why it is known for its Bourbon Trail. Similar to Napa Valley, the Kentucky Bourbon Trail consists of over 15 distilleries across the state of Kentucky that are open for tours, tastings and other bourbon themed experiences. This was obviously the focal point of our visit, so most of our time was spent along this trail and the Kentucky Bourbon Trail Craft Tour.

I plan to do a full post on how to plan a weekend doing the bourbon tour in the coming days, but in the meantime, we ended up visiting five distilleries for a tasting or tour, plus two others, where we just stopped in their visitor’s centers and gift shops. COVID restrictions made accessing the distilleries a bit trickier with limited reservations and filling up incredibly fast, but we still loved our experience. We started the weekend off with a cocktail at Woodford Reserve before a quick visit to the campus of Buffalo Trace. After perusing the gift shop for a bit, we headed to Lexington’s Distillery District for tours and tastings at James E. Pepper Distillery and Barrel House Distilling, both which had an incredible history and offered interesting facts about the bourbon making process.

The next day, we headed south towards Bardstown, for our tours and tastings at Maker’s Mark and Lux Row Distillery. We originally had another tasting scheduled but realized it was too close to another tour time and instead decided to spend extra time at Maker’s Mark. Maker’s Mark was by far the best overall experience out of all of the distilleries we visited, but we were surprisingly pleased with our visits at the others, especially since we weren’t as familiar with the brands!

The Kentucky Castle

I stumbled across this venue when looking up restaurants in the Lexington area, not thinking much of it since I figured Jody wouldn’t have much of an interest in dining in a castle. However, I was proved wrong when we first drove past The Kentucky Castle headed towards Woodford Reserve. We called the next day to see if they had any available for brunch on our last morning in Kentucky, figuring they were booked, but were excited to learn that they did, in fact, have an open reservation available. When we arrived for our reservation, we had a bit of time to wander the grounds and rooftop before our seating. It was such a gorgeous venue, with stunning views of the rolling hills and thoroughbred horse farms of Kentucky.

While we only dined at this farm to table restaurant, the castle also serves as a hotel, spa, and event venue. Tours are also available to learn more about the history and design of this picturesque landmark. If anything, I highly suggest making a reservation for brunch! The service was amazing and of course, the food and drinks were delicious!


As an avid horse-lover and equal derby fan, I was dying knowing we’d be in the horse capital of the world and not be doing anything horse related. I had heard about Keeneland, and had actually looked at tickets for an early morning tour of the facilities, but tickets were super limited since their Spring Meet was running through the month of April. We already had tours booked at the distilleries on Friday and Saturday, but there were still a few General Admissions tickets left for Sunday. I ended up deciding not to book them since the first post wasn’t until early afternoon and with the 9+ hour drive we had home, it just didn’t seem like it would work.

However, while on the drive back to Lexington from Bardstown on Saturday, I saw that The Spot Properties, a new rental company in Lexington, was giving away two tickets to Sunday’s races. I entered, figuring I wouldn’t win (I never win giveaways!), but that evening, I received a DM from Spot Properties that I did, in fact, win the tickets. While I was hesitant to accept, knowing that we had a long drive home, Jody insisted that we go.

So, after our brunch at the castle on Sunday morning, we headed for an afternoon of racing at Keeneland. I could not contain my excitement as we walked through the gates. The grounds were stunning, and there was a buzz throughout the grand stand as we headed towards the track. We made it to the viewing area just in time for the first post, and were completely captivated the second the gates opens by the thunderous sound of the thoroughbreds galloping around the track, the cheers increasing as the horses rounded the final bend, and the adrenaline of the horses passing the finish line right in front of us! It was even more spectacular than I ever imagined.

There was roughly a 40-minute wait between races, which gave us plenty of time to view the horses, browse the gift shop, and visit the bourbon bar for a cocktail. We don’t know anything about betting, so we didn’t partake in that aspect of the event, but noticed there was table where you could learn more about the sport of horse betting. It also tickled me that there were televisions everywhere, including by the drinks and concessions so the employees could also view each race. It is very evident that Keeneland is a cherished Lexington tradition.

We stayed for four of the races before needing to being our journey back to Maryland, but were so glad that we had the opportunity to attend Keeneland. If you are ever in the Lexington area during race season, visiting Keeneland is a must. Also, be sure to check out The Spot Properties if you are looking for a vacation rental in Lexington!

Food + Drink

One of our favorite things about traveling is testing our favorite local establishments. Shelby, of Glitter and Gingham, so graciously shared some suggestions of her favorite places to eat in Lexington, and we enjoyed checking them out. I had heard great things about Carson’s, but were disappointed to learn they had almost a two-hour wait. We ended up deciding to wait it out, which was a great decision, since we only waited about 10 minutes to be seated. Jody and I each ordered a bourbon cocktail (both were good, but Jody’s Campfire cocktail was to die for) and we split the Chicken Fried Chicken entree with gouda Macaroni and Cheese. It was a tasty dinner to kickoff our weekend.

Corto Lima also came highly regarded, so we enjoyed our second dinner in Lexington there. There was a bit of wait since it was a Saturday night, but we didn’t mind. We waited at a nearby cocktail bar until the rain stopped, and then headed back to Corto Lima for our seating at the bar. A few rounds of margaritas, queso, shrimp ceviche, and pulled pork tacos later, we were full and happy. While Latin-inspired cuisine wouldn’t necessarily be the first thing I think of when dining in Kentucky, I’m certainly glad we went!

I already mentioned that we enjoyed brunch at The Kentucky Castle, but honestly it was so good, it is worth mentioning again. Knowing it would be our primary meal for the day, Jody and I each ordered a separate dish to share – the country breakfast bowl and the country ham and brie sandwich. We also enjoyed breakfast at Josie’s on Saturday morning before our day of bourbon tours and tastings. I would be remiss if I didn’t mention Crank + Boom, a hand-crafted, local ice cream spot. They have tons of different flavors including ice cream cocktails, but we enjoyed the Bourbon and Honey and the Blackberry and Buttermilk flavors.

There you have it!! If you stuck with me this far, you deserve a bourbon cocktail! 🙂 We definitely didn’t have enough time to do everything while in Kentucky, but we felt like we hit the highlights in our weekend getaway. We loved Kentucky so much and look forward to visiting again!

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