Lexington, Kentucky

Fast Facts

A city built on politics and horse racing, Lexington evidences its place in history in grand, historic landmarks coupled with larger-than-life thoroughbred facilities.

Overall Rating: 3.5/5 stars

Travel Date(s): July 1, 2017

Time on the Ground: 10 hours

Pizza Rating: 6/8 pizza slices!

Walkability: 2/5 stars – Historic downtown is walkable, but you need a car to get there from the airport. Many of the other sights, such as horse farms and Ashland, are too far to walk to from downtown.


Airport Rating: 5/5 stars – Personally, we love small airports—security is a breeze and they often have excellent free Wi-Fi to use during delays! Not to mention, the baggage claim chime is the sound of the Charge theme from the races—such a nice touch.

Airplane: CRJ-200

Free Walking Tour (Self-Guided): Although short, the guide was very informative. The tour took us about 30 minutes, but we did not do every single part of it. Pick up a map at the visitor center!

Lay of the Land

Lexington, Kentucky, is the second largest city in Kentucky and is located fairly centrally in the state. The city is known as the horse capital of the world for its plentiful thoroughbred horse stables and race tracks. Known as the Athens of the West in the 19th century, it was considered one of the best educated and most civilized cities in what was known as the “West.” Due to the extremely short nature of this quick trip, we did not stay in any hotel accommodations.


The first stop on our trip was Keeneland—a thoroughbred horse racing complex right outside of the Lexington airport (LEX). We started the the morning with breakfast at the Track Kitchen, a cafeteria-style canteen. On our way there, we walked through the barns where stable teams were washing horses down after their morning training ride. Afterwards, we attempted to take the tour of the grounds but realized that the tour was only offered at 8:30 in the morning. Instead, we toured the grounds ourselves and then made our way into the city. We would definitely recommend a short trip to Keeneland if you are passing through. The grounds are absolutely breathtaking, it is easy to get around, and it’s conveniently located right beside the airport.

Visitors Center & Downtown Lexington

We made our way downtown, which was about a 15-minute drive from the airport and Keeneland area. There is not a lot of street-level parking, but there are parking decks, including one directly attached to the Victorian Square Shoppes building, that are inexpensive and provide plenty of options. We parked for a couple hours and it only cost us $3. The visitors center is worth a stop in its own right as they had several mini-exhibits about Lexington’s history, bourbon distilling, and horse racing. They were also very willing to help answer any questions and provide directions, including a map with a self-guided walking tour of the area.

Mary Todd Lincoln House

We walked a block and half over from the visitors center to the historic home of the Todd family, which included Mary Todd Lincoln—wife of President Abraham Lincoln. The tour cost $12 a person for adults and lasts about an hour. We had to wait about an hour for the next available tour, so be sure to go online ahead of time if you are time constrained. Overall, the tour was well worth the time and money. The house is Mary’s father's and she only lived in the house a handful of years. However, the staff at the house uses this small time window of Mary’s life to delve into the many complex topics of the mid-1800s. Our tour guide, Jenny, was extremely knowledgeable, managed the tour group well, and was able to answer all of our questions. The home was restored in the 1950s by a nonprofit created with the help Mary Todd Lincoln’s family and is filled with a mix of original family pieces and period pieces similar to those the family would have owned. For those who love Civil War-era history, or history in general, this is a must-see in Lexington.

Self-Paced Walking Tour

After a quick lunch at Pies & Pints, we decided to take a leisurely walk around historic downtown Lexington. The tour was provided by the visitors center and had a map as well as numerical stops throughout the route that provided background information about the houses and buildings along the way. Physically, the tour was very pleasant and easy to do—the tree-lined streets provided shade from the sun and the fact that it was self-paced allowed you to take your time up and down the few hills as you wind your way through the historic neighborhoods. Many of the houses date back before the Civil War and provide a firsthand glance into the early days of American history. On the tour, you can see sights such as Transylvania University, the first university West of the Mississippi River, and one Henry Clay’s early law offices. We highly recommend the self-paced tour as a great way to see American history at your own pace (and it doesn't hurt that it is free).

Ashland (Henry Clay’s Estate)

The last tour of the day took us to the estate of Henry Clay, who is considered one of the most famous U.S. senators in American history. Clay was one of the favorite sons of Kentucky (though he’s actually from Virginia) and is best known either being the most successful senator in history or the least successful presidential candidate (he ran unsuccessfully five times). In all seriousness, his influence in the Senate was renowned and he is credited for playing a vital role in the compromises of 1820, 1833, and 1850 (when he was brought out of retirement and back to the Senate to assist in negotiations). All of these compromises made temporary peace between the North and the South, delaying the Civil War.

Similar to the Mary Todd Lincoln house, Ashland is maintained by a local nonprofit rather than any government body. The Henry Clay Memorial Association was founded in 1926 as a way for the family to preserve the estate without requiring a family member to live at and maintain the estate by themselves. The tours are $12 and can be reserved ahead of time or booked in person, if availability permits. We were visiting on a Saturday and had to wait until the next tour (typically one every hour) for a spot.

Overall, the tour and grounds are worth visiting. Our guide was a former history teacher and loved to tell a good story. He went into great detail about the Clay family, the estate itself (the structure is actually not the original but the building that Henry Clay’s son rebuilt), the political and cultural context surrounding Henry Clay’s life, and Clay’s political career and impact on the world around him. At times, the tour did feel a bit like we were viewing history through rose-colored glasses, but the information was accurate and interesting. For any history buff visiting Lexington, this is a must-see! Taking the tour, walking the grounds ourselves, and glancing through the gift shop, we spent around 1.5 hours at the estate. Following the tour, we hopped in the car and headed to the LEX airport to wrap up our quick trip!


Our day trip to Lexington, Kentucky, was a step back in time. Although the city has a great downtown area with shops and restaurants near Rupp Arena (go Tar Heels!), you would be remiss if you made a stop in Lexington without taking the time to see one of the several pre-Civil War landmarks around the city. It is an opportunity to see American history firsthand.

There were a couple items that stood out to us during our visit as well. First, everything is connected to horses. The city is extremely proud of its horse racing heritage and if we were to go again, we would dedicate more time to learning about the history of the industry and touring some of the horse farms. The second is that both of the major historical sites we visited are managed by nonprofits that charged for a tour. Although the fees were minimal (at $12 each), it was a stark difference from many East Coast cities where the major historical sites are open to the public for free or run by the government instead. In the end, it seems to provide a better experience—the tours at both locations were excellent and the grounds were well maintained.

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