Day 1: Morning
Pictured here: Stella's Kentucky Deli, located in downtown Lexington
Ease into your three-day Lexington stay with a delicious breakfast at the always charming Stella’s Kentucky Deli. You can’t go wrong with the melt-in-your-mouth pancakes at this laid-back local favorite.
Then, for a change of scenery, head to Kenwick Table for fantastic coffee in another community-minded shop that’s quickly become a cornerstone of the flourishing Kenwick Neighborhood. You’ll be a stone’s throw from the Ashland Estate, 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.
Keep it casual with another 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.
Day 1: Noon
Pictured here: Fresh Bourbon Distillery
Now that you’ve worked up an appetite, take a little drive to Boonedogs for lunch with a distinctly Bluegrass view. This family-friendly spot located amongst rolling hills and picket fences is known for dressed-up hot dogs, but bourbon, beer, and cocktails are also on the menu.
Speaking of bourbon, an afternoon Distillery Tour would be a good move right here. There are plenty to choose from, and you can opt to book your experience through a tour company if you want a pro to handle the details.
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 at ItalX. Elevated contemporary Italian cuisine and a robust wine list are the hallmarks of this elegant restaurant, the perfect preamble to a show at the Lexington Opera House before calling it a night.
Day 2: Morning
Pictured here: Martine's Pastries, located on East Third Street
Get Day 2 started in Lexington’s East End with a sweet and savory breakfast at Martine’s. This upscale French bakery has an exquisite selection of traditional pastries and a breakfast menu to match.
Martine’s coffee is excellent, but if you’re feeling adventurous you can get a cup of something extra special at The Greenery on Main Street. Bask in their cozy vibes for a while before setting out to explore the city at your own pace on the VisitLEX Downtown Walking Tour.
Day 2: Noon
Pictured here: Kentucky Theatre, located in downtown Lexington
End your walking tour with lunch downtown, too. Pearl’s is a cool spot with wood-fired bagel sandwiches during the day. 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 one of the best burgers in town.
An afternoon at the movies might be considered a waste on most getaways. Not so in Lexington. Catching a matinee at the historic Kentucky Theatre is a nostalgic experience you won’t find at modern megaplexes. Check their schedule for showings of contemporary indie films and old cult classics that you’ll rarely get the chance to see on the big screen.
Day 2: Evening
Pictured here: Corto Lima, located in downtown Lexington
After a little rest and a change of clothes back at your homebase, head back out on the town around sunset. Grab a glass of wine and browse thought-provoking art in the galleries of 21c Museum Hotel. You could do 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.
Day 3: Morning
Pictured here: Keeneland Morning Workouts
Get the most out of your last day in town. 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 you’re there, check out the Keeneland Morning Workouts or take a tour of the spectacular grounds at this National Historic Landmark. If it’s a raceday, you’ll definitely want to stick around for at least a couple hours to catch the excitement.
Day 3: Noon
Pictured here: Darby Dan Horse Farm
After a day at the track, you could squeeze in some shopping and a bite to eat at The Summit at Fritz Farm. Or you could take the scenic route with a drive through the Bluegrass countryside on your way to lunch at Windy Corner Market.
After lunch, 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 3: Evening
Pictured here: The Burl in Lexington's historic Distillery District
Finally, put a bow on your three-day Lexington getaway with an evening of local food, drinks, and entertainment in the Distillery District. There’s several restaurants and bars within walking distance so you can try a little of everything. Then wander over to The Burl for some dreamy live music that will have you planning your return trip before you even leave.
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.
