Lexington, Kentucky

Best Things to Do in Lexington

BY Michele Laufik | January 14, 2021

Welcome to Fifty Grande’s Best of the U.S. Bucket List series. This is your one-stop travel guide to the best, most unique and quintessential experiences of a city, state or event. Want to know how to “do” Lexington? We’ve got you covered. Curated by experts, vetted by in-the-know locals, this is all you need to have the best trip ever. If we’ve written a Bucket List, we recommend you go. If it’s on this list, it’s the best the city has to offer right now. Consider this your one-stop answer to “What are the best things to do in Lexington?”

You might assume that Lexington is all about bourbon and horses. Well, you’re not totally wrong. But the city does offer a range of other activities and attractions and more to drink than the brown stuff (hello, Ale-8-One). And it’s hard not to be seduced by its Southern charms and friendly folks. Y’all just need to follow the Kentucky Bourbon Trail (but be sure to venture off as well), take in views of the rolling acres of the surrounding horse farms and grab some good eats. These are the best things to do in Lexington right now.

SEE HOW BOURBON IS MADE

Whether you’re a connoisseur or a total novice, you’ll leave Lexington with a greater appreciation of the amber-hued spirit that’s synonymous with Kentucky. There are a slew of bourbon and whiskey distilleries across the state, and plenty that are a stone’s throw from Lexington. Book a tour and learn about the art of making bourbon (it’s all about the corn) and get a taste of the many brands that call the Bluegrass State home.

Buffalo Trace Distillery in Lexington, Kentucky. Photo cred Shutterstock.
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Buffalo Trace Distillery in Lexington, Kentucky. Photo cred Shutterstock.

Buffalo Trace Distillery

113 Great Buffalo Trace, Frankfort, KY, USA

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.

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Woodford Reserve Distillery in Lexington, Kentucky. Photo cred Shutterstock.
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Woodford Reserve Distillery in Lexington, Kentucky. Photo cred Shutterstock.

Woodford Reserve Distillery

7785 McCracken Pike, Versailles, KY, USA

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.

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Maker’s Mark Distillery in Lexington, Kentucky. Photo cred Shutterstock.
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Maker’s Mark Distillery in Lexington, Kentucky. Photo cred Shutterstock.

Maker’s Mark Distillery

3350 Burks Spring Rd, Loretto, KY, USA

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.

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Four Roses Distillery in Lawrenceburg, Kentucky. Photo cred Shutterstock.
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Lawrenceburg, KY, USA - November 6, 2016 : Inside tour at historic Four Roses Bourbon Distillery. Fresh corn mash bubbling and fermenting.

Four Roses Distillery

1224 Bonds Mill Rd, Lawrenceburg, KY, USA

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.

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Wild Turkey Distillery in Lexington, Kentucky. Photo cred Shutterstock.
#5
Wild Turkey Distillery in Lexington, Kentucky. Photo cred Shutterstock.

Wild Turkey Distillery

1417 Versailles Rd, Lawrenceburg, KY, USA

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.

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Limestone Branch Distillery in Lexington, Kentucky. Photo cred Shutterstock.
#6
Limestone Branch Distillery in Lexington, Kentucky. Photo cred Shutterstock.

Limestone Branch Distillery

1280 Veterans Memorial Hwy, Lebanon, KY, USA

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.

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Independent Stave Company in Lexington, Kentucky.
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Independent Stave Company in Lexington, Kentucky.

Independent Stave Company

711b E Main St, Lebanon, KY, USA

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.

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YOU’LL NEED TO VISIT THE HORSES, OF COURSE

While Louisville is where the most famous racetrack in the country, Churchills Downs, is located, Lexington is home to perhaps the prettiest, as well as acres and acres of horse farms where you can see the majestic creatures up close and personal.

Keeneland in Lexington, Kentucky. Photo credit Shutterstock.
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Keeneland in Lexington, Kentucky. Photo credit Shutterstock.

Keeneland

4201 Versailles Rd, Lexington, KY, USA

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.

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Spendthrift in Lexington, Kentucky.
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Spendthrift in Lexington, Kentucky.

Spendthrift Farm

884 Iron Works Pike, Lexington, KY, USA

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.

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The Kentucky Horse Park in Lexington, Kentucky. Photo credit Shutterstock.
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The Kentucky Horse Park in Lexington, Kentucky. Photo credit Shutterstock.

The Kentucky Horse Park

4089 Iron Works Parkway, Lexington, KY, USA

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.

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SAVOR SOME SOUTHERN HOSPITALITY

One thing’s for sure, you definitely won’t go hungry when visiting Lexington. There are lots of restaurants, gastropubs and bourbon bars to feed your need for Southern comfort. Some local specialties to keep an eye out for include bourbon balls, deviled eggs, burgoo (a Southern stew typically served with cornbread), spoon bread, beer cheese and country ham.

Bluegrass Tavern in Lexington, Kentucky.
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Bluegrass Tavern in Lexington, Kentucky.

The Bluegrass Tavern

115 Cheapside, Lexington, KY, USA

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.

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Justin's in Lexington, Kentucky.
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Justin's in Lexington, Kentucky.

Justins’ House of Bourbon

601 W Main St, Lexington, KY, USA

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.

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Honeywood in Lexington, Kentucky.
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Honeywood in Lexington, Kentucky.

Honeywood

110 Summit at Fritz Farm #140, Lexington, Ky.

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.

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Holly Hill Inn in Lexington, Kentucky.
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Holly Hill Inn in Lexington, Kentucky.

Holly Hill Inn

426 N Winter St, Midway, KY, USA

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.

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WHERE TO GET GRUB AFTER A NIGHT OF BOURBON IMBIBING

Here’s how you survive a hangover in Lexington.

Wild Eggs in Lexington, Kentucky.
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Wild Eggs in Lexington, Kentucky.

Wild Eggs

3735 Palomar Centre Drive, Lexington, KY, USA

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.

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KENTUCKY HISTORY GOES BEYOND BOURBON MAKING

Get an unstuffy view of the state’s past and its prominent historical figures by exploring estates, mansions and even a nature sanctuary.

Ashland: The Henry Clay Estate in Lexington, Kentucky. Photo credit Shutterstock.
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Ashland: The Henry Clay Estate in Lexington, Kentucky. Photo credit Shutterstock.

Ashland: The Henry Clay Estate

120 Sycamore Rd, Lexington, KY, USA

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.

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Mary Todd Lincoln House in Lexington, Kentucky. Photo credit Shutterstock.
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Mary Todd Lincoln House in Lexington, Kentucky. Photo credit Shutterstock.

Mary Todd Lincoln House

578 W Main St, Lexington, KY, USA

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.

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Waveland State Historic Site in Lexington, Kentucky. Photo credit Shutterstock.
#18
Waveland State Historic Site in Lexington, Kentucky. Photo credit Shutterstock.

Waveland State Historic Site

225 Waveland Museum Lane, Lexington, KY, USA

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.

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Raven Run in Lexington, Kentucky.
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Raven Run in Lexington, Kentucky.

Raven Run Nature Sanctuary

3885 Raven Run Way, Lexington, KY, USA

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.

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COOL PLACES TO STAY

In addition to the usual hotel chains, there are a few standout properties in and around Lexington that can add some charm to your visit.

21C in Lexington, Kentucky.
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21C in Lexington, Kentucky.

21c Museum Hotel Lexington

167 W Main St, Lexington, KY, USA

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.

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The Kentucky Castle in Lexington, Kentucky. Photo credit Shutterstock.
#21
The Kentucky Castle in Lexington, Kentucky. Photo credit Shutterstock.

The Kentucky Castle

230 Pisgah Pike, Versailles, KY, USA

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.

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WATCH THE CATS PLAY

Be sure to don your royal blue and white and practice your C-A-T-S chants before heading to watch a U.K. basketball game, which is on par with attending church service in the state.

Rupp Arena in Lexington, Kentucky. Photo credit Shutterstock.
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Rupp Arena in Lexington, Kentucky. Photo credit Shutterstock.

Rupp Arena

430 W Vine St, Lexington, KY, USA

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.

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NABE TO KNOW

Lexington Distillery District in Lexington, Kentucky. Photo credit Shutterstock.
#23
Lexington Distillery District in Lexington, Kentucky. Photo credit Shutterstock.

Lexington Distillery District

1170 Manchester St, Lexington, KY, USA

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.

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