We’ve all been there: Someone’s trying to give you directions by describing 10 lefts, 20 rights, and a jumble of cardinal directions. Isn’t it easier to just point out a landmark?
That’s exactly what we’re doing. We have 11 of the most recognizable Lexington landmarks — from The Kentucky Theatre to the Parkette sign. Not only are these local icons easy to remember, but they’ll also get you where you need to go in a jiffy.
Address: 100 Midland Ave.
Nearby: A Cup of Common Wealth, Carson’s
Scattered throughout the park are various statues + plaques paying tribute to our rich Thorougbred horse racing tradition. The entrance to the park features the finish line of a race with the flowing fountains symbolizing the cheering of the crowd.
Ashland, the Henry Clay Estate
Address: 120 Sycamore Rd.
Nearby: Euclid Avenue businesses
What served as the original estate and home of Henry Clay, this piece of Lexington history now lives on as a museum + park. The surrounding grounds are a popular spot for photos with its manicured gardens and colorful flowers. It’s also a favorite for seasonal Sunday yoga classes and leisurely walks.
The Kentucky Theatre
Address: 214 E. Main St.
Nearby: Central Library, Phoenix Park
This historic theater originally opened in 1922 + recently celebrated its 100th birthday. Find classic films during the summer months, new features throughout the year, and a variety of events.
Address: 1230 E. New Circle Rd.
Nearby: Lexington Peddlers Mall, Woodhill Circle Plaza
The classic drive-in diner opened in 1952 + saw many changes and additions throughout its ~70 year lifespan in Lexington. The beloved spot closed in the summer of 2022, and while the business itself was demolished, the community favorite neon sign continues to grace the skies. The owners are working on getting a roadside historical marker for spot.
Address: 430 W. Vine St.
Nearby: Triangle Park, Bigg Blue Martini, Hyatt Hotel
Synonymous with basketball greatness, Rupp Arena is home to our Kentucky Wildcats, the Big Blue Nation, and so much more. Comedy + musical greats — like Dave Chappelle, Elton John, and New Kids on the Block — have all graced the stage there throughout the years. In 2022, the $310 million renovation to Rupp Arena and the Central Bank Center.
Kentucky Horse Park
Address: 4089 Iron Works Pkwy.
Nearby: Spindletopp + Red State BBQ
Spanning over 1,200 acres, the Kentucky Horse Park is an international equestrian competition venue, home to a working horse farm, and museums. Here you can see world class competition, the towering draft horses, or hit the trails on horse or foot. Be sure to stop by during the holiday season for Southern Lights.
Mary Todd Lincoln House
Address: 578 W. Main St.
Nearby: Central Bank Center, Justins’ House of Bourbon, and Sorella Gelateria
Nestled just on the outskirts of downtown is the childhood home of former first lady Mary Todd Lincoln. It’s open seasonally (March 15-November 20), available for individual tours, kids take-home activities, and special events.
Address: 4201 Versailles Rd.
Nearby: Blue Grass Airport, Calumet Farm, and the city of Versailles
From the picturesque tree-lined entry way, to the thundering of hooves on the track, our historic racetrack brings thousands of fans from all over the world each year. Experience it yourself during the race meets (April + October), the various sales season, or during its quiet time for a tour, a meal, or a visit to the Keeneland Library.
Address: 2450 Old Frankfort Pike
Nearby: Headley Whitney Museum + various horse farms
The 3,800-lbs bronze statue of Secretariat serves as a welcome to drivers along Lexington’s national scenic byways, Old Frankfort Pike. The Visitors Viewing Area even features interpretive panels that tell stories of the area.
Address: 430 W. Vine St.
Nearby: Triangle Park, Bigg Blue Martini, Central Bank Center
This towering 70-ft linear sculpture originally called at Ashland, the Henry Clay Estate its home before being moved downtown in 2022. The public art piece was created by native Lexingtonian John Raymond Henry + serves as a focal point outside of the Central Bank Center.
The Big Blue Building
Address: 250 W. Main St.
Nearby: Lexington Marriott City Center, Jeff Ruby’s + 21c Museum Hotel
We couldn’t release a list of local landmarks without mentioning the Lexington Financial Center building. The Big Blue Building, aka “The Tallest Building in the World” is 31 floors high + home to Fifth Third Bank.
What did we miss? If you know a landmark that’s not on the list, let us know.