Best Things to Do in Lexington

Located just outside the state capital of Frankfort, Buffalo Trace isn’t listed as an official stop on the Kentucky Bourbon Trail, but this low-key distillery is definitely worth a visit. Learn about some bourbon legends, including E.H. Taylor, Jr. and Pappy Van Winkle, as you wander among the barrels resting in aging warehouses. Plus, you might be able to score a bottle of the elusive Blanton’s Single Barrel.

Another historic barrelhouse, Woodford Reserve, located along Glenn’s Creek, is considered Kentucky’s oldest and smallest distillery and is the only one that makes its bourbon in copper pot stills.

Here, you can immerse yourself — and any naked bottle of bourbon — into the production process, thanks to a D.I.Y. dipping station that allows visitors to adorn their souvenirs (a.k.a. booze) with the brand’s signature red wax. Located in Loretto, between Lexington and Louisville, this distillery is a bit off the beaten path, which means cell phone service can be spotty, so jot down the directions before hitting the road.

Built in the style of a Spanish mission, the Four Roses Distillery stands out from the rest of the stone and wood structures that dominate the state’s other distilleries. You can also book a tour at the Four Roses Warehouse & Bottling Facility, which is located in Cox’s Creek.

Wild Turkey’s higher-than-normal 101-proof expression is the reason this brand is so beloved — or feared. FYI: This is another one of those hard-to-find spots, so plan your trip accordingly.

Found between Maker’s Mark and the Independent Stave Company’s Kentucky Cooperage, this craft distillery was opened by two brothers, Steve and Paul Beam (yes, that Beam), and is credited with restoring the Yellowstone label.

This is where you can get a behind-the-scenes look at how they craft barrels and casks, a factory known as a cooperage. Most travelers who visit Kentucky focus on the good stuff inside the barrels, but watching how they make the containers that hold the spirits is just as cool to see.

Those in the know cite this racecourse as the one to visit, especially during the spring and fall (in particular, the first three weeks of April or October). That’s when the two racing seasons happen. Tours of the grounds are also available throughout the year.

At this thoroughbred racehorse breeding farm, you can learn how such a property operates and meet some famous horses. This is the place that sired the 2020 Kentucky Derby and Breeders’ Cup Classic winner: Authentic. To get more info on Spendthrift Farm tours and others, check out visithorsecountry.com.

This family-friendly complex dedicated to all things equine features a range of attractions including the International Museum of the Horse, which explores the history of horses and their impact on human civilization; trail and pony rides (during the warmer months); and the Parade of Breeds Show.

This downtown watering hole claims to have the state’s largest bourbon collection, but who’s counting. There’s bourbon, people! Of course, other spirits like vodka, tequila and rum, as well as wine and craft beer, are also available for those who have had their fill of whiskey.

Just down the street, you’ll stumble upon another impressive bourbon selection at the aptly named Justin’s House of Bourbon. But be prepared to pay crazy secondary market prices for rare finds.

To soak up some of that bourbon, head to one of renowned chef Ouita Michel’s restaurants, Honeywood, where you can fill your belly with down-home comfort food like deviled eggs, beignets, fried chicken and all the fixins.

This is Michel’s flagship fine-dining restaurant, located in Midway (between Frankfort and Lexington), which serves upscale Southern food like guinea hen brined in apple cider and beef tenderloin Diane with mushrooms.

Originating in Louisville, this franchise eatery serves hearty (a.k.a. large portion) breakfast staples like biscuits and gravy and country-fried steak and eggs, as well as a housemade cinnamon roll that’s the size of a small dinner plate.

Explore this historical site and get to know Henry Clay, a statesman who represented Kentucky in both the Senate and House and was appointed Secretary of State by President John Quincy Adams. The estate is comparable to visiting other properties like Mount Vernon, Monticello, The Hermitage and Montpelier.

This was the childhood home of Mary Todd, the future first lady and wife of the 16th president, Abraham Lincoln. Today, the 14-room house serves as a museum showcasing period furniture, portraits and artifacts from the Todd and Lincoln families. It’s located in downtown Lexington, near Rupp Arena, so it’s easy to squeeze in some sightseeing while exploring.

Also known as the Joseph Bryan House, this Greek Revival home and plantation, which is now part of the Kentucky state park system, offers the usual historic tours, as well as afternoon tea service, picnic areas and a quaint quarter-mile trail, so you can experience history without the boring bits.

Raven Run is a 734-acre nature sanctuary that’s considered a Lexington city park, so it’s free of charge to enter. Here, you can explore roughly 10 miles of trails; grab a map at the on-site Nature Center before you head out. Numerous 19th-century remnants of early settlers, as well as over 600 species of plants, providing an outdoorsy look at early Kentucky history.

Inside the historic Fayette National Bank Building in downtown Lexington, 21c Museum Hotel Lexington is both a chic boutique property and a contemporary art museum with specially commissioned, site-specific works.

If the Queen had a Southern accent, this is where she’d stay. Set in a medieval-style castle on scenic grounds with landscaped gardens, this stately bed and breakfast includes suites with four-poster beds and turrets.

Home of the University of Kentucky Wildcats, this arena, located in the heart of Lexington, hosts a roster of events such as concerts and other sporting events, in addition to those famous basketball games.

Home to the historic James E. Pepper Distillery, the Lexington Distillery District is a revitalized area located a few miles from downtown that’s anchored by two working bourbon distilleries (Pepper and Barrel House) and features plenty of shops, food and drink spots such as Goodfellas Pizzeria, serving New York-style pizza, Ethereal Brewery, and even an axe-throwing joint. Plus, this is where you see a show when in Lexington. The Burl is a restored train depot that’s the perfect place to catch live music from local and national bands. And the Manchester Music Hall was originally (guess what?) a bourbon warehouse for the Old Tarr Distillery; it’s now an event and concert venue.