How to Get a Taste of Lexington, Kentucky in Only 48 Hours (2024)

Day 1: Morning

First, consider staying at the 21c Museum Hotel Lexington, an eclectic art hotel located right on Main Street. Along with enjoying an award-winning, 4-star hotel, you’ll be centrally located downtown and within walking distance of good food and nightlife.

10 a.m.: Begin your visit to the Bluegrass region by meeting some of the majestic thoroughbreds that are so widely celebrated. Book a tour with Old Friends, a thoroughbred retirement and rescue farm located just 20 minutes north of Lexington (take US-25 for a more scenic drive). The 90-minute tours are memorable, informative, and support a good cause. The Kentucky Horse Park is a nearby alternative; time your visit to catch the daily Parade of Breeds show at 11 a.m.

12 p.m.: For lunch, you have the option of heading further afield to Wallace Station, a notable eatery on the Bourbon Trail with outside seating. Afterward, return to town by driving the scenic KY-1681 (Old Frankfort Pike). If you prefer to clean up a little for lunch, return to the hotel before walking to nearby Zim’s Cafe or Stella’s Kentucky Deli; both are popular favorites that source ingredients locally.

Day 1: Afternoon

1:30 p.m.: Walk next door to the Lexington Visitors Center, located in the iconic old courthouse (the same building as Zim’s Cafe). You can grab maps for a self-guided walking tour and learn a lot from the displays, but more importantly, the friendly folks there can give you a heads-up about events and festivals. When the weather is nice, Lexington seems to always have some sort of (usually free) outdoor event happening. You’ll often get to hear local bands and socialize with welcoming residents.

2 p.m.: How you spend your afternoon depends on your interests. For a quick tour of the nearest bourbon distillery, head over to the nearby Lexington Brewing Company or the James E. Pepper Distilling Company; both are within city limits and offer guided tours of their distilling operations.

If you’re more interested in Lexington’s history, audio guides for walking tours are available for free on the Lexington Public Library website. You can begin by walking down Main Street to tour the Mary Todd Lincoln House, where the First Lady lived until 1839. Afterward, stroll through Gratz Park and appreciate the lovely neighborhood that was home to some of Lexington’s most notable residents in the 1800s. Next, wander the grounds of Transylvania University, established in 1780 as the first college west of the Allegheny Mountains. Don’t worry: All of these places are within a 10-minute walk of your hotel!

5 p.m.: You can claim to have seen Lexington's cute-but-compact downtown area from end to end by walking 20 minutes the other direction, past the old courthouse, then on to Thoroughbred Park at the intersection of Main Street and Midland Ave. The bronze art installation of jockeys racing atop their life-size horses makes for a great photo opportunity. Pass by and appreciate some of Lexington’s many impressive street murals on your way back to the hotel.

Day 1: Evening

6 p.m.: Begin your evening by checking out the fun art in your own hotel, if you haven’t already. Grab an aperitif from Lockbox, the hotel bar and restaurant, to sip while you explore the lobby and second-floor galleries.

7 p.m.: Next, plan to enjoy one of Lexington’s many fine dining establishments. Dudley’s on Short has been a classic on the scene since 1981. Try ItalX for Italian food in a lively setting, or Tony’s of Lexington for steak. If you want authentic French cuisine and talked-about mussels, grab a sidewalk table at Le Deauville on North Limestone. For something more casual, there are plenty of reasonably priced eateries in the neighborhood.

11 p.m.: Before retiring upstairs to your room, pay attention to the large, glowing orbs hanging inside Lockbox. If they’re blue and yellow, you’ll enjoy a sunny day tomorrow. If they’re gray, pack an umbrella!

Day 2: Morning

On Saturdays: Begin your day by strolling Lexington's Saturday Farmers Market next to the old courthouse. The atmosphere is pleasant, and you can grab a coffee while browsing art and local products. Musicians from the Lexington Philharmonic and other performers are often on the scene.

8:30 a.m.: If you’re visiting Lexington in April or October when the races are running at Keeneland, your entertainment for the day is already a given. Regardless, you should still get to the internationally-renowned racecourse for a visit. The general public is invited to enter for free to watch the early morning training runs from 6 a.m. to 10 a.m. You’ll get to see jockeys, trainers, and thoroughbreds at work in an informal setting. Paid tours are available, or you can simply wander around the beautiful venue yourself.

11 a.m.: If you’ll be returning later for the races, plan to eat a hearty lunch outside of Keeneland to hold you until dinner. Drive over to Malone's in Palomar or Ramsey’s Diner on Old Harrodsburg Road—both are popular local chains enjoyed by Lexingtonians. If you’re feeling brave enough to try a Hot Brown, an infamously delicious-but-heavy Kentucky creation, the one at Ramsey’s is a hit.

Day 2: Afternoon

1 p.m.:The horse racing at Keeneland is a cultural phenomenon that has to be experienced. Don’t worry if you aren’t into betting: Many visitors never even watch a race! The grounds and pageantry are stunning, and the respectful energy as horses are shown in the paddock between races will become a highlight of your trip to Lexington. Gates open at 11 a.m., and the first race is at 1:05 p.m.

For enjoying time outdoors in a beautiful setting other than Keeneland, consider driving to the UK Arboretum, Kentucky’s state botanical garden. You can do a hike or just admire the impressive horticultural displays; entrance is free. Another great option for some local history is Ashland, the Henry Clay Estate, former residence of the ninth U.S. Secretary of State. Wandering the beautifully manicured grounds is free, but for a real treat, consider taking a one-hour tour of the mansion to see how the famous statesman would have lived in the 1800s. For some air conditioning after a hot afternoon of walking, the University of Kentucky Art Museum is free and only five minutes away.

4 p.m.: Whatever you do, beat the Keeneland traffic out! Since you’ll be on the south end of Lexington after the races, stop in at Joseph-Beth Booksellers in Lexington Green to peruse the large selection of books by local authors. For more local souvenirs, Artique (located in Fayette Mall across the street) sells beautiful gifts and work created by Kentucky artists. Plenty of additional shopping, mostly upscale, is available in The Summit at Fritz Farm not far away.

Day 2: Evening

7 p.m.: Head back downtown to begin celebrating your Keeneland winnings—or forgetting your losses. Start with some small plates and top-shelf tequila at Corto Lima, a perpetually busy downtown institution with sidewalk seating. An alternative could be to grab one of the exquisite charcuterie boards and a delicious co*cktail at The Grove, a cozy, outdoor spot hidden behind Harvey’s Bar. If the University of Kentucky is playing basketball, expect a lively scene throughout the city as fanatical fans gather to cheer for their Wildcats.

9 p.m.: Get serious about celebrating with one of the Instagramable co*cktails from Pour Decisions on East Main Street. If you prefer your bourbon neat, step inside Bourbon on Rye. You won't have much trouble finding live music in the area. North Limestone is lined with additional eateries and bars, including Minglewood—a spot known for late-night food (until 11 p.m.) and craft co*cktails.

In the morning, if you have time to kill before a flight or could use some help recovering, return to Keeneland one last time—Lexington's Blue Grass Airport is conveniently just across Versailles Road. Take the road next to Barn 20 until it ends at the Keeneland Track Kitchen, a Lexington “secret” where you can enjoy a hearty, inexpensive breakfast while doing some interesting people-watching. You’ll often be joined by famous trainers, owners, and jockeys!