My First Road Trip From Louisville to Lexington-Ky

By Kathy Condon Freelance Travel Writer

I was asked to cover the Chilled Magazine 100 Elevate Conference in Louisville. One hundred and sixty bartenders would come together to visit distilleries and attend seminars that would help enhance their skills. My role was to capture the event in writing.

Before making airline reservations, I heard a quiet voice say, “Kathy, take a road trip to Lexington.” I’d had seen pictures and movies of Kentucky roads with white picket fences, and something inside of me alerted me it was time for me to explore and see for myself.

Preparation for the Trip

Looking at my calendar, I decided I could take three days to explore. I would also fly back to Palm Springs from Lexington and save $100 on an airline ticket instead of Louisville. The journey between Louisville and Lexington is 72 miles. It was apparent I would need to rent a car. Since I was on my own, I explored places to stay. After researching several options, I found an Airbnb located on the beltway surrounding the city of Lexington.

The Journey Begins

Early on, I had decided to take the backroads to Lexington. I wanted to get a view, even with a short trip, a taste of Kentucky’s countryside. I picked up the rental car at the Louisville Airport, got directions, and headed out of Louisville.

Once leaving the city limits, I smiled as I saw my first white picket fence. On rolling hills surrounding a large farm were horses grazing on Kentucky bluegrass.

Further down the road, I was alerted to a scenic spot. I pulled over, and right before me was Kentucky’s capital. Construction towers shielded part of it. However, it was evident it is a majestic building.

A little further down the road, signs pointed to historic downtown Franklin. I followed the signs downtown.

It was one of those Hallmark quaint towns. Alas, I was on a mission to get to Lexington. I noted that I wanted to come here and explore in the future.

Woodford Reserve Distillery

Frankly, I wasn’t planning on stopping at another distillery since I had seen three in Louisville. However, I was ready for a break, so I made the turn to the Woodford Reserve Distillery. Both sides of the road had white picket fences. Large trees surrounded the entire drive, sometimes forming a cathedral-like arch as I drove the approximately two miles to the distillery.

The building, where the tastings are held, was modern and comfortable and took full advantage of its strategic location on a hill. Patrons were sitting on the patio sipping their craft cocktails and meeting new friends who had come there from all over the country.

Thinking I had seen enough gift shops in the last few days, I was inclined to skip this one. However, people I met in the tasting room building said I absolutely should make a stop. I listened to them and drove a short distance to the gift shop parking lot.

This gift shop was a step up from anyone I had ever seen. Beautiful dark wood shelves had bottles of bourbon lit from behind. If you wanted a special gift, you could get a band engraved for a bottle of bourbon you want to present to someone. A variety of Bitters and a box of bourbon candy caught my attention.

A Castle in Kentucky

With Country Music playing on the radio, I continued my journey. Then, off to my left, I couldn’t believe what I saw: a castle on the top of the hill. Yes, I’m talking about the kind of castle one might see in Europe.

Surely, there must be a story about it, so I took the road up it. Once I got closer, it was even bigger than I had initially thought. I walked into the front entrance, and the grand staircase was right before me. A restaurant and a gift shop were off to the left. Off to the right was a beautiful ballroom-like room used for events.

The story is about a man who built the castle for his fiancée. They broke up, and the place languished there for years. Now it is The Kentucky Castle Hotel, with gardens, rooftop terraces, and farm-totable fine dining. A separate building on the site houses the Spa--The Kentucky Castle.

Exploring Downtown

With rain pattering on the window, there was a strong inclination to pull the covers up and stay in bed. However, I was here to learn about Lexington, so by the time I had a shower, the sun was again shining brilliantly.

Mary Todd Lincoln Childhood Home

My first stop was Mary Todd Lincoln’s Childhood home. Admittedly, I drove by it three times. I was expecting a tiny log cabin-like home surrounded by highrise buildings since it was downtown.

Then I saw the sign. I parked in the back and returned to the Main Street entrance. There in front of me was a large building. Mary’s father was a banker. The home was a former tavern and came up for sale during foreclosure. He bought it and made it into a five-bedroom house for his seven children.

The tour of the house illustrated this was a family of means. Abraham Lincoln stayed here for three months before he became president. Many of the artifacts in the house are original, including the candlesticks used in the Whitehouse.

Another factoid of interest. This was the very first home preserved in memory of a First Lady of the United States.

Downtown Dining

After touring Todd’s home, it was time for lunch. I decided to wander on my own and enjoyed seeing the antebellum-type homes on the back streets.

I loved the sign on The Blue Herson Steakhouse. It was closed, but peeking inside, I loved the use of all the plants and the openness of the restaurant. I researched, and locals said this is one of the places to go if you are looking for a good steak.

Directly across the street was The Goose. I wandered into the casual entrance and was escorted to the patio, embracing greenery from the outside hedge. Here, patrons gathered around tables for apparent lunch meetings.

Since I was in bourbon country, I figured I couldn’t go wrong with pork chops with apple butter bourbon sauce. The portion was huge and smothered in the sauce. My first bite had me, and it was so delicious and perfectly prepared. My first thought was that I needed to duplicate this entrée.

Restored Courthouse

I was determined to meet the staff of the Visit Lexington Visitors Center. Much to my pleasure, they are housed in the Historic Courthouse. The building has been refurbished, with the only original feature saved, the beautiful wooden floor in the Center.

There is a hip new restaurant, and offices occupy the upper floors. This is a delightful reminder of what forward-thinking city officials can create if they hitch onto their imagination.

Taking the Advice of the Visitor Center

My mentor, Mary Charlebois, had told me while in the area that I might want to check out Keeneland Racetrack. I was planning to go there in the afternoon. However, staff at the Visitor Center of Lexington suggested I go there in the morning instead.

I had a 2 p.m. flight the next day, and they said that was perfect because the Keeneland Racetrack was literally across from the Airport. I listened to them and am so glad I did.

After packing, I headed to the Keeneland Racetrack, an easy commute since I was on the beltway around Lexington. I parked my car and marveled at the trees that lined the entire racetrack grounds. As they suggested, I headed down to the racetrack. Seeing the jockey taking the thoroughbreds out for a workout around the track was a thrill. I love that the jockeys knew we were there and came close to the rail so we could see the horse and its power.

I tagged along on a tour and learned there was a thoroughbred sale at the auction building. What a special moment to walk into the building and see buyers bidding on thoroughbreds as the horses were brought on the stage in the exhibit hall. Each bidding opportunity lasts an average of 90 seconds: one of the thoroughbreds sold for 1.3 million dollars the day before.

Time to head to the Airport.

It was time to return the rental car and check in for my flight back to Palm Springs. Once I was settled into my seat on the airplane, I smiled. From day one, I knew this side trip was an extra expense, but the small voice was so persistent, and I was proud of myself for listening to it.