Day 1: Morning
Pictured here: DV8 Kitchen, located in downtown Lexington
Ease into your three-day Lexington stay with a delicious breakfast at the excellent DV8 Kitchen. In addition to serving one of the best brunches in the city–with breads made fresh daily in its bakery–this local favorite is making a real impact by creating opportunities for people in recovery to build a better life. Come support a great mission and try out some amazing menu items, like a melt-in-your-mouth bacon, egg and cheese sandwich.
If you’re visiting in the summer, a little outdoor exploration is an absolute must. Keep it casual with a leisurely walk around The Arboretum, the State Botanical Garden of Kentucky, where plants and trees from Kentucky’s seven distinct regions can be seen on 100 acres accessible by meandering paths.
Feeling adventurous? Head to Raven Run Nature Sanctuary for over 10 miles of scenic hiking trails. Wind through meadows, woodlands, and streams and catch stunning views of the Kentucky River. Or take in the beauty of the Bluegrass from 200 feet high at Boone Creek Outdoors, where expert guides lead you through nature on sky bridges, staircases, and ziplines as long as 1,400 feet!
Day 1: Noon
Pictured here: Ashland Estate
Now that you’ve worked up an appetite, take a little drive to Boonedogs for lunch with a distinctly Bluegrass view. Located amongst rolling hills and picket fences, this family-friendly spot is known for dressed-up hot dogs, but bourbon and cocktails are also on the menu.
Later on, head to Kenwick Table for a glass of wine and live music in the flourishing Kenwick Neighborhood. You’ll be a stone’s throw from the Ashland Estate, home of the famous 19th-century statesman Henry Clay, so now is the perfect time to pop over for a guided tour or just a stroll around the beautiful grounds and the famous English parterre garden.
Day 1: Evening
Pictured here: Lexington Opera House, located in downtown Lexington
As evening approaches, make your way back to your hotel or short-term rental to freshen up for dinner downtown. A local staple since 1981, Dudley’s on Short balances upscale elegance with comfort, an inventive menu, and excellent service. Just down the street, ItalX offers elevated Italian cuisine with a robust wine list. And Table 3TEN, a recent addition to the West Short Street corridor, brings global flavors, creative cocktails, and a refined atmosphere from an award-winning team.
Any of these spots make the perfect preamble to a show at the Lexington Opera House or a movie at the historic Kentucky Theatre before calling it a night.
Day 2: Morning
Pictured here: Keeneland Morning Workouts
Set your alarm a little early and enjoy a hearty homestyle breakfast at the Keeneland Track Kitchen surrounded by the trainers, jockeys, and other players that help make Lexington the Horse Capital of the World.
While racing pauses for the summer, Keeneland’s grounds remain open to visitors. Watch Lexington’s four-footed celebrities in action at the Morning Workouts or take a tour of the spectacular grounds at this National Historic Landmark. Then keep the thrills coming with a ride on Rail Explorers in nearby Versailles—where you’ll pedal past horse farms and rolling countryside, get an up-close look at the layered limestone that filters water used to make the world’s best bourbons, and take in awe-inspiring views of the Kentucky River.
Later, get up close and personal with Lexington’s world-famous Thoroughbreds on a Horse Farm Tour at one of the region’s 450+ working horse farms. You can also go behind the scenes at other equine facilities like training centers, hospitals, and feed manufacturers.
Day 2: Noon
Pictured here: Darby Dan Horse Farm
After a morning getting familiar with Lexington’s famous equine culture, squeeze in some shopping at The Summit at Fritz Farm. Then go browsing for hidden treasures at Failte, a charming Irish shop filled with unique finds, before a mid-day cocktail stop at Harvey’s Bar & Beer Garden.
Prefer to take the scenic route? Take it slow with a leisurely drive through the Bluegrass countryside on your way to lunch at Windy Corner Market.
Day 2: Evening
Pictured here: The Burl in Lexington's historic Distillery District
After a little rest and a change of clothes back at your homebase, head back out on the town with an evening of local food, drinks, and entertainment in the Distillery District. There are several restaurants and bars within walking distance so you can try a little of everything. Enjoy the Bluegrass’s best tiki cocktails on a tropical rooftop oasis at Lost Palm, or—for something even sweeter—a boozy float at Crank & Boom. Then wander over to The Burl to catch up-and-coming musical acts before their big break.
Day 3: Morning
Pictured here: Lussi Brown Coffee Bar
Get your last day started with a pick-me-up from the cozy and always excellent Lussi Brown Coffee Bar. Still thirsty? Grab a beverage (and snag a selfie in front of the outside mural) at A Cup of Commonwealth, a welcoming space dedicated to serving coffee and the local community. Or treat yourself to something special at The Greenery on Main Street, a welcoming and vibey new café surrounded by other women-owned businesses.
Bask in the laid-back atmosphere for a while before setting out to explore the city at your own pace on the VisitLEX Downtown Walking Tour. While you’re downtown, be sure to swing by the Lexington Visitors Center to explore local guides to the city’s top attractions, get hands-on with interactive displays, and pick up blue horse merch and other unique keepsakes to bring home.
Day 3: Noon
Pictured here: Castle & Key Distillery in Frankfort, KY
No trip to Lexington is complete without an afternoon exploring our region’s rich bourbon heritage on a Distillery Tour. But first, time to fuel up. After the Visitors Center, take a 15 minute walk for the sweet and savory brunch of your dreams at Martine’s. This upscale French bakery has an exquisite selection of traditional pastries and a breakfast menu to match.
If you’d prefer to stay close to downtown, Pearl’s is a cool spot with wood-fired bagel sandwiches during the day–perfect before a big day of Bourbonland exploration. Zim’s Cafe has sandwiches, salads, and Southern classics. Courtyard Deli is a longtime favorite lunch spot in a church turned antique shop. And Sidebar is a tiny but mighty dive with the best burgers in town.
Now, time for bourbon. When it comes to distillery tours, there are plenty of options to fit your style—from the historic grounds of James E. Pepper Distillery and Castle & Key, which operates at the site of the Old Taylor Distillery built in 1887, to the state-of-the-art craft facilities at Bespoken Spirits—and you can opt to book your experience through a tour company if you want a pro to handle the details.
Bourbon may have put us on the map, but craft beer fans will also find plenty to love in Lexington. Grab a patio view and pints along the Brewgrass Trail, a self-guided tour of the region’s top breweries. Mirror Twin Brewing is a summer staple, known for always having twin drafts on tap that are nearly identical in grain recipe. Nearby, Ethereal Brewing serves fresh brews in the historic Distillery District, and Wise Bird Cider Co. offers small-batch heritage ciders made with high-quality, locally sourced apples.
Day 3: Evening
Pictured here: Corto Lima, located in downtown Lexington
Finally, to put a bow on your three-day Lexington getaway head back out on the town around sunset. Grab a craft cocktail and browse thought-provoking art in the galleries of 21c Museum Hotel. You could enjoy a fantastic dinner right there at Lockbox, or spice things up at Corto Lima around the corner.
If you’re ready to wind down, after-dinner drinks in the moody ambiance of Ona is a relaxing way to end the evening. Want to keep the party going? Dance the night away and see what’s happening in the cabaret at The Bar Complex.
Looking for something lower-key but still stylish? Head to Epping’s on Eastside for elevated seasonal fare and a quiet nightcap to toast the final night of your Bluegrass journey—and start planning your next Lexington adventure.
Contact Us
Need a hand planning your three-day Lexington getaway? The hospitality pros at the Lexington Visitors Center are here to help. Contact us to get started.
