Lexington is famous for being the horse capital of the world and is the second biggest city in Kentucky. While Kentucky isn’t everyone’s first choice for a vacation, Lexington is a fun destination full of history, art, and natural attractions. The 3-day guide will show you how to spend your time and have an amazing and unforgettable weekend in Lexington.

This site contains affiliate links to products. I may receive a commission for purchases made through these links at no extra cost to you. There are only products included that I truly love. I APPRECIATE your support!
Table of Contents
To get to Lexington, visitors have the option of driving themselves or flying to the closest airport. Lexington Airport (LEX) is the closest and most convenient airport to land being only 7 miles from the city.
Visitors also have the option to fly into Louisville (SDF) or Cincinnati-Covington (CVG), however only do this if you are renting a car, and be prepared for a drive as these airports are close to 75 miles away from Lexington.
Kentucky is a state that offers residents and visitors all four seasons, depending on the time of year. The best weather conditions and an ideal time to visit is during late Spring and early Fall. Temperatures are ideal, with sunny skies. June hosts the Bluegrass Festival every year which is a fantastic event in Lexington, while the Fall season kicks off college sports with the University of Kentucky being Lexington’s home college.
Traveling to Lexington with your furry best friend? Check out this dog-friendly Lexington guide!
Lexington is a rather small city, and most landmarks and attractions are located in the downtown area. It is a very walkable city with a variety of hotels and guesthouses for every type of budget. Most hotels themselves will also be located in the downtown region, some favorites and top-rated ones being The Marriott, Holiday Inn, Hyatt Regency, and Glo Best Western.
There are a few hotels outside of the city, or more rural guest houses the further you go. Staying outside of the city may save you some money on accommodation, but there is little public transportation outside of downtown. So unless you have a vehicle, downtown areas are recommended.

Morning:
To commence the weekend in Lexington, start at Keeneland Race Track. Since Lexington is known for horses, it’s a good place to begin your weekend of exploring. It is a professional and public racing track for horses. Enjoy the atmosphere while watching a real Lexington race day. There are also tours of the facilities available for the real equine lovers.
Afternoon:
Throughout the afternoon, explore all of the old historical houses and sights within the city. Be sure to check out the Henry Clay Estate, Mary Todd Lincoln House, the Hunt Morgan House, and Waveland State Historic Site. There are also various restaurants located throughout the city within walking distance to grab a bite for lunch.
Looking for a more adventurous way to explore the city? Check out one of Let’s Roam’s Lexington scavenger hunts! You can compete with friends, learn more about the history, and find unique spots throughout the city!
Evening:
For your first night in Lexington, the best place to eat by far is the Blue Door Smokehouse. Get a real taste of southern cooking and real American barbeque. Try to make a reservation ahead of time if possible, seats fill quickly as dinner is only served Friday and Saturday nights.

Morning:
Begin your day with a nature hike at Raven Run Nature Sanctuary. Located in the south of Lexington, its purpose is to preserve the natural greenery of Kentucky and the River Palisades. There are over 10 miles of trails for visitors to enjoy, as well as yoga classes and a visitors center to learn about the history and previous settlers in the area.
Afternoon:
After a bite to eat and a rest from the morning adventure, head downtown to visit the Monroe Moosnick Medical Science Museum. This is one of the most unique things to do in the city, maybe even the state. The Museum features medical equipment and instruments from the 1700s. Diagrams and models are there to help guide you and teach visitors the background.
Looking for a more adventurous activity for your afternoon? Try a guided zipline tour and check out the Boone Creek Gorge (from above) during this canopy tour. Complete with 6 ziplines, a rappel, and other obstacles.
Evening:
A trip to Lexington isn’t complete without an evening spent at the Kentucky Theatre. This landmark has been around for over a century and is by far one of the biggest highlights in town. It is now used as a modern-day cinema, showing old blockbuster movies and the occasional indie film as well.

Morning:
The Kentucky Bourbon trail is something that could easily last the entire weekend in itself. The whole state is famous for its bourbon, so a visit isn’t complete without a small taste. There are various stops within the city to fill a morning, and give you a quick preview. If you are interested in completing the entire trail, you’ll definitely have to plan a longer trip to Kentucky!
Afternoon:
After a morning of drinking, head over to Thoroughbred Park. The Thoroughbred Park is one of the best things in town for horse lovers, and other tourists as well. The park is dedicated to thoroughbred horses and their history in Lexington, and a great afternoon spent admiring all the statues, plaques, and scenery.
Evening:
To end your weekend in Lexington, start the evening with the Old Kentucky Chocolates Tour. Some of the best chocolate in the country comes from this factory, and the tour allows visitors to observe the creation process. Don’t forget to taste test and buy some take-home candy from the gift shop. End your evening with dinner (from the food truck) and drinks at West Sixth Brewery. If you are a fan of craft beer and homemade booze, there is no better place to end your trip.

Lexington is within a few hours driving distance of various other natural wonders in Kentucky. If you love a good adventure and the outdoors, consider using Lexington as a home base while traveling throughout the state.
As you can see, there’s SO much to do in Lexington that one weekend would never be enough to see it all. You can customize your 3-day Lexington itinerary based on what interests you. No matter what you’re looking for, you’ll find plenty of entertaining activities to create your own fun-filled, jam-packed adventure weekend in Lexington!
What else would you add to this “One Weekend in Lexington, KY” Itinerary?
Tip! Make sure to follow me on Instagram for more USA weekend getaways and dog-friendly adventures!
Be the first to comment