The 22 Best Things To Do In Lexington, Kentucky

It's easy to overlook Lexington at first, in the shadow of Louisville, which gets most of the attention thanks to the Kentucky Derby and Whiskey Row. Yet, Lexington quietly enjoys the spoils of being a thriving town set in the ecologically stunning Kentucky landscape. From bourbon distilleries and horse racing to breezy Bluegrass hills and a vibrant downtown, you're never short on places to explore and local businesses to duck into. Lexington is perfectly placed for a getaway with so many activities to put on your list, no matter if you go during the blooming spring, colorful autumn, or snowy winter.

 Here are the best things to do on your next trip to Lexington, Kentucky.

Explore Horse Country

Tour Keeneland Race Track

Dubbed a National Historic Landmark, Keeneland has helped keep the tradition of Thoroughbred racing alive for over eight decades. Moreover, the lush grounds are expertly crafted and kept up and worth a visit on their own. Year-round, you can book a morning tour that shows the early training sessions, as well as teaches guests about the history of Keeneland and thoroughbred racing.

keeneland.com, 4201 Versailles Rd, Lexington, KY 40510

Attend the Keeneland Races

The horse-racing events in Kentucky are set apart from other sporting events due to the pomp and circumstance that surrounds them. Spectators are expected to dress to the nines—hats, ascots, and all—to sip on mint juleps and bet on quirky-named horses. At Keeneland, you can plan a visit during the Spring Meet or Fall Meet.

keeneland.com, 4201 Versailles Rd, Lexington, KY 40510

Visit a Retirement Home for Racehorses

At Old Friends, a retirement farm for Thoroughbreds whose careers have ended, Michael Blowen gives racehorses the best kind of Kentucky retirement. When Blowen decided to start a retirement farm for racehorses, people were skeptical. "They all thought I was nuts," he says. Today, Blowen oversees three farms that serve as the residence for 260 retired or elderly horses. You can visit the main facility at Dream Chase Farm in Georgetown, Kentucky, and get the chance to meet past champion horses.

oldfriendsequine.org, 1841 Paynes Depot Rd, Georgetown, KY 40324

Reserve a Tour at Famed Horse Farms

Prestigious operations such as Claiborne Farm, Spy Coast Farm, and Ashford Stud (home of Triple Crown winners American Pharoah and Justify) offer a fleeting glimpse into a largely exclusive world. You're able to book public group tours ahead of time, and therefore craft your own itinerary. During the tours, expect to learn the history of often generational horse farms, meet past champion horses, and take in the scenic views.

Take Advantage of Kentucky Horse Park

Opened in 1978, the Kentucky Horse Park is the world’s only park dedicated to teaching people about horses and helping take care of and showcase the majestic animals. During most of the year, the park is home to up to 100 horses representing more than 25 different breeds. While you can explore the museum, visitor's center, and horse stalls, there is no better way to immerse yourself in horse culture than embarking on the guided 35-minute trail ride, which is suitable for first-time riders and takes you along the outskirts of the park.

kyhorsepark.com, 4089 Iron Works Pkwy, Lexington, KY 40511

Follow The Bourbon Trail

Tour the Reader-Voted "South's Best Distillery"

There are 46 stops that make up the Kentucky Bourbon Trail, but amongst the many options, make sure to plan a visit to what our readers previously voted the "South's Best:" The Woodford Reserve Distillery. The official bourbon of the Kentucky Derby, Woodford Reserve has garnered icon status since its founding in 1812, and even still uses a track system from the 1800s to roll barrels into the warehouses. Tours include bourbon tastings, and a visit to the Woodford Reserve Welcome Center comes with excellent cocktails and expert pours, as well as sweeping views from the veranda.

woodfordreserve.com, 7785 McCracken Pike, Versailles, KY 40383

Taste More Than Just Bourbon

Beyond just bourbon, there are some distilleries offering a unique range of distilled products. Castle & Key Distillery, located half an hour from downtown Lexington in Frankfort, also offers tastings of its in-house gin and vodka that will appeal to those who don't prefer bourbon. Make sure to roam the gorgeous grounds that once housed the Old Taylor Distillery, a romantic castle built in the 1800s.

castleandkey.com, 4445 McCracken Pike, Frankfort, KY 40601

Explore More Well-Known Bourbon Legends

Fortunately, there is a distillery for practically every taste here. Heirloom distilleries such as Buffalo Trace and Maker's Mark are sure-fire delights for a bourbon lover. The Maker’s Mark distillery is exactly what you hope a bourbon distillery will look like: a large black barn with cherry red shutters, the old homestead (now a visitors center) tucked beneath shade trees, landscaped paths, and a trickling stream named Whisky Creek. In downtown Frankfort, not far from Lexington, Buffalo Trace feels like an industrial frontier town, with most of the buildings on the 118-acre campus built before Prohibition.

Pay Visits to Small-Batch Bourbon Makers

Luckily, the industry hasn't stopped at the big names. Embark on the Kentucky Bourbon Trail Craft Tour to hit unique and newer small-batch labels with fresh perspectives. There are 28 stops to choose from, including Bluegrass Distillers which has a downtown Lexington location available for visits. For those hitting the road, family-run Brough Brothers Distillery—the first Black-owned microdistillery in Kentucky—offers tasting and tours in the Park Hill area of Louisville, only a little over an hour's drive away from Lexington.

Check Out The City

Spend an Evening in the Distillery District

The Distillery District—housed in the Historic James E. Pepper Distillery, which had previously sat abandoned for five decades—is now the place to go to have a little tour of everything that Lexington has to offer, including working bourbon distilleries, restaurants, bars, and shops. Make a stop at the Barrel House Distillery, a craft distiller on the Kentucky Bourbon Trail; try authentic Kentucky burgoo at the Elkhorn Tavern; and listen to music at Manchester Music Hall, which is located in the circa-1800s bourbon warehouse of Old Tarr Distillery.

lexingtondistillerydistrict.com, 1228 Manchester St, Lexington, KY 40504

If You Haven't, Try Ale-8

Ale-8-One—called Ale-8 for short—is a gingery, citrusy soft drink that tastes like a crisper, more mellowed take on ginger beer, and it's the only Kentucky-invented soft drink still being produced. The first batches were bottled in 1926, making it over 90 years old. Head to the downtown rooftop of Belle's Cocktail House, and order a "bourbon & Ale-8."

bellesbar.com, 156 Market St, Lexington, KY 40507

Explore Downtown Lexington

Downtown Lexington has plenty of entertainment to spend a day exploring. On weekends, stop by the Lexington Farmers' Market. Peep the many murals throughout the city blocks. Head to The Square—a block of renovated Victorian-style buildings—to see the art scene at Plymale Gallery, Main Cross Gallery, and the Artist Attic. On the same block as the 21c Museum Hotel is Bourbon on Rye, a modish take on a moody bourbon bar, where some truly well-versed bartenders will happily guide you without breaking the bank.

Where To Eat

Enjoy Southern Cuisine at Dudley's On Short

A Lexington institution for nearly 40 years, Dudley's On Short is the perfect spot to grab a Southern-inspired upscale lunch or dinner, located in a circa-1880s bank. No meal is complete without "Dudley's Eggs," which are the perfect deviled egg bites to split. The brunch-and-lunch menu has standout shareables, including bacon beignets and smoked trout dip.

dudleysonshort.com, 259 W Short St #125, Lexington, KY 40507

Start or End Your Day at Pearl's

A bagel shop by morning and pizza-and-wine bar by evening, Pearl's in downtown Lexington is our kind of all-day café. The breakfast bagels are hand-rolled and honey-boiled, and the wood-fired pizza is delightfully poofy and charred, perfect for sharing with family and friends with a bottle of all-natural wine, which the restaurant specializes in.

pearlspizzapie.com, 133 N Limestone, Lexington, KY 40507

Indulge in Kentucky Barbecue at Blue Door Smokehouse

You'll find the best brisket in the area at Blue Door Smokehouse, hands down. Opened in 2013 by two Lexington natives, this BBQ joint doles out sandwiches and plates piled high with the smoked meats of your choice. Ask for the "Blue Door Special" to sample all the proteins in stock on any given day.

bluedoorsmokehouse.com, 226 Walton Ave, Lexington, KY 40502

Try the Latin Cuisine at Corto Lima

This Latin-inspired restaurant is run by James Beard-nominated chef Jonathan Lundy. At Corto Lima, you can expect a mix of flavor-packed dishes, such as shrimp ceviche, adobo chicken, and rock crab empanadas. Start with a batch of guacamole and a house margarita to wash it all down.

cortolima.com, 101 W Short St, Lexington, KY 40507

Grab a Slice at Missy's Pies

A local favorite since 1989, Missy's Pies offers the best homemade slices of delectable pies in town. Flavors vary according to day and season, but look out for customer-beloved options such as the chocolate-and-peanut butter "Combo" Pie, Black Bottom Banana Pie, and Coconut Cream Pie.

missyspieshop.com, 502 E High St, Lexington, KY 40502

Where To Stay

Stay at an Award-Winning Museum Hotel

Located in downtown Lexington, the artsy 21c Museum Hotel is housed in a historic bank building. Except now, it offers such contemporary perks as a contemporary art museum and a notable in-house restaurant, Lockbox. Explore the exhibits between comings and goings.

21cmuseumhotels.com/lexington, 167 W Main St, Lexington, KY 40507

Stay in the Distillery District

Located in Lexington's restored Distillery District walkable to the many restaurants and shops, The Manchester feels perfectly suited to the historic and soulful nature of Lexington. The interiors' supple leather and rich, earthy tones mimic the surrounding Bluegrass hills and Kentucky Bourbon Trail distilleries. The hotel offers 125 rooms with a bespoke bottle shop, lobby bar, and two in-house dining options—Appalachian-inspired Granddam—and rooftop bar Lost Palm.

themanchesterky.com, 941 Manchester St, Lexington, KY 40508

Stay at a Hip Pet-Friendly Hotel

The Elwood Hotel is adorned with a colorful mural on the front facade, and you can expect similar energy on the inside with vibrant art and decor. The 62-room boutique hotel is also welcoming to those with pets and has an in-house restaurant. Fiddletree Kitchen & Bar, located in the lobby, is open for breakfast, lunch, and dinner for indoor dining, as well as an outdoor terrace with firepits. 

theelwoodhotel.com, 444 Parkway Dr, Lexington, KY 40504

Make A Rural Pitstop

Stop for Lunch at Wallace Station Deli

Make a pit stop at Wallace Station Deli near Midway, one of well-known Kentucky chef Ouita Michel's places. The 15-minute drive to Wallace Station from the highway will take you past some of the area's showiest horse farms. Order one of the Inside Out Hot Browns (their take on a classic Kentucky sandwich) and a cold bottle of Ale-8.

wallacestation.com, 3854 Old Frankfort Pike, Versailles, KY 40383

Tour the Kentucky Castle

One of the more unique landmarks you'll come across while driving around Kentucky's bourbon trail and horse country region, the Kentucky Castle offers various experiences, including tours of the castle grounds, themed dinners, or farm days. You can even stay on the grounds for an extra magical trip.

thekentuckycastle.com, 230 Pisgah Pike, Versailles, KY 40383