15 Romantic Things to Do in Lexington, Kentucky

Saddle up for a romantic ride through the Horse Capital of the World.

Lexington street

 Whitney Neal Studios

Though Kentucky straddles the borders of the Midwest and the South, any Lexingtonian will be proud to let you know that "Southern hospitality starts here." If you’re hankering for a sweet, small-town escape with big-city amenities, look no further than Lexington and you’ll find a vibrant cultural atmosphere nestled in the heart of Horse Country. 

With a walkable downtown area, a sophisticated dining scene, and an endless array of outdoor activities, Mary Quinn Ramer, president of VisitLEX, shares why Lexington is a haven for a couple’s getaway or staycation.

Meet the Expert

Mary Quinn Ramer, president of VisitLEX, has more than 15 years of tourism experience and is active with numerous tourism-related organizations, including board membership on Kentucky Travel Industry Association, Equestrian Events International, LexArts, and Horse Country LLC.

A year-round destination with exciting happenings during any season, the spring and fall in Lexington are especially pleasant with average temperatures around 66 degrees Fahrenheit. "In the spring, travelers can don their race day best and bet on Derby-qualifying races at Keeneland Racecourse’s Spring Meet," says Ramer. "In any season, visitors can tour dozens of championship thoroughbred farms with Visit Horse Country and check out Kentucky’s famed bourbon distilleries, the Donut Trail, and the craft beer Brewgrass Trail."

In the past two years, Lexington has undergone a complete renaissance but is still under the radar—and that’s a good thing. Ramer says the city is a hidden gem for travelers that don’t want to break the bank as it’s more affordable than some of its more Southern counterparts (sorry, Nashville!). Visitors can expect to spend anywhere from $50 to $100 per day on meals, activities, and experiences, and beautiful boutique accommodations offer rates as low as $137 per night.

With a range of activities for any duo to enjoy, we’ve rounded up some of the most romantic things to do in Kentucky for couples below.

The current outbreak of coronavirus (COVID-19) has been declared a pandemic by the World Health Organization. As the situation remains fluid, we’ll be sharing tips and stories from industry experts to give you of-the-moment advice and help you navigate wedding planning today. For the most up-to-date guidelines and latest on travel restrictions and requirements, check the CDC and U.S. Department of State websites.

01 of 15

Have Dinner at a Castle

Aerial view of The Kentucky Castle as Sunset

Hide away behind the limestone walls of The Kentucky Castle, naturally located in Versailles—a neighboring city—and treat yourselves like royalty. The castle was inspired by a six-month European honeymoon and aimed to bring the best features of the continent’s palaces to the heart of the Bluegrass State in the name of love. Once an exclusive members-only club, the Castle Farm restaurant inside is now open to the public for evenings of elevated farm-to-table fare that pair perfectly with a flight of bourbon.

02 of 15

Shop Til You Drop

Swing by The Summit at Fritz Farm to spoil each other with a shopping spree from over 60 street-level boutiques featuring fashion and food from a collection of national brands and local favorites. Once you’ve worked up an appetite, treat yourselves to dinner at Ouita Michel’s Honeywood for a fresh take on Southern fare featuring locally grown ingredients complemented by contemporary cocktails.

03 of 15

Get Racy in the Morning

Thoroughbreds racing on a dirt track at Keeneland Racecourse

Start your day off at the Keeneland Racecourse with breakfast at the Track Kitchen where you might rub elbows with some of the country’s leading jockeys and trainers. From there, head to the track and get an up-close look at the heart-pumping action while watching the thoroughbred’s morning workouts. Then, slow things down with a self-guided tour over the rolling landscape of the internationally renowned racecourse’s grounds.

04 of 15

Do Date Night at a Supper Club

Sneak off to the city’s secret enchanted garden and embark on an ephemeral culinary journey at Apiary. As part of their Omage series, an ever-evolving menu is inspired by the places and artists driving the world of innovative cuisine. Nestled amidst lush greenery and twinkling candlelight, you’ll settle in for a gastronomic experience complemented by a full bar, curated wines, and a rotating selection of cocktails inspired by the menu of the moment.

05 of 15

Make a Stop at Greyline Station

Exterior the Greyline Station storefront

Originally constructed over 100 years ago, Greyline Station has been reborn as the city’s newest neighborhood meeting place to eat, shop, and recreate. Formerly housing bus and transit companies, the station is now home to local vendors and small businesses as the host of the Julietta Market. Line up your visit with the first Friday of every month so you don’t miss the Block Party—a social outing filled with friendly faces, great food, and live entertainment.

06 of 15

Leave a Piece of Your Love Behind

At DV8 Kitchen, couples can grab a paintbrush and participate in a community-driven art project together with the East End Rock Project. The eatery hosts regular painting parties where everyone is welcome to lovingly leave a mark on the community by placing their handpainted rocks around the restaurant’s perimeter. Best of all, "artists" receive 50 percent off the menu, which includes scratch-made baked goods like croissant-style cinnamon rolls and southern biscuits.   

07 of 15

Hunker Down at Your Hotel

Interior of the lobby at The Campbell House in Lexington

Escape to a hotel with equestrian heritage and enjoy regionally-inspired cuisine at Rackhouse Tavern in The Campbell House. The bar also features an impressive selection of over 300 local brews and bourbons from the classic Woodford Reserve to the exotic Pappy Van Winkle. Pop culture-loving couples can book a room at 21c Museum Hotel Lexington to be transported into a scene from Netflix’s Lexington-based series Queen’s Gambit. The hotel’s Harmon Room captivates guests through its locally sourced mid-century modern décor, vintage accessories, chess books and sets, and custom artwork.

08 of 15

Find Endless Entertainment Under One Roof

It’s game on for competitive partners inside the new 90,000 square-foot entertainment venue known as LexLive. Play as a team or go head-to-head on state-of-the-art bowling lanes (including four private VIP lanes) and over 90 interactive arcade games. Cash in your points at the prize counter and then celebrate together over a couple of drinks at one of the three full-service bars.

09 of 15

Head Out for a Hike

View of The Kentucky River Palisades in Fall

Carved deep into the heart of the state, a series of steep, striking gorges and limestone bedrock make up the scenic Kentucky River Palisades Trail where you can lace up your boots and step out to hunt for the perfect picnic spot. The hike is especially scenic in the fall when the air is crisp and the changing leaves frame the Kentucky River with fiery-colored foliage along the lower loop.

10 of 15

Embrace a Higher Love on a Zipline Tour

Outdoorsy couples will gain new perspectives traversing over a spectacular gorge before strapping in for an exhilarating thrill with one of Boone Creek Outdoors's zipline tours. You’ll bond over the adrenaline as you venture through the six zip lines, three sky bridges, a rappel, and floating staircase all overlooking incredible scenery from the top of the canopy.

11 of 15

Spend a Day at the Farms

Exterior shot of a white stable and hilly landscape on a horse farm in Lexington

Couples would be remiss not to visit some of the globally renowned thoroughbred farms—you are in Horse Country, after all! Make it a date and book a private tour so the two of you can leisurely explore pristine acres of the undulating landscape and maybe have the chance to meet famed equine athletes like Triple Crown winner American Pharoah.

12 of 15

Stroll Through the Street Art

Yellow Louis Armstong mural that says "I love you" in Lexington, Kentucky

Art lovers can amble through the city’s downtown area to explore over 30 imaginative street art installations woven throughout. Discover the hidden gems and the giant masterpieces by challenging each other to see who can track down more of the murals by the end of the day.

13 of 15

Delight in the Distillery District

With the completion of Town Branch Commons, couples can hit the shared-use trail downtown for a bike ride straight into the Distillery District. The 25-acre property is easily walkable so it’s perfect for a bites-and-beverage crawl; start with a tasting and tour at the historic James E. Pepper Distillery, break for a New York-style slice at Goodfellas, grab a beer at Ethereal Brewery, and have a seat for some small plates at Middle Fork.

14 of 15

Go on an Ice Cream Date

A flight of ice cream at Crank & Boom Craft Ice Cream in Lexington

After a day in the Distillery District, share a sweet treat from one of the city’s favorite locally-owned ice cream parlors. Pop into Crank & Boom Craft Ice Cream and go half on a Sampler Flight for Four or go for a dessert-turned-night cap with a Spiked Scoop. Over at Sav’s Restaurant and Gourmet Ice Cream, you can explore West African flavors with the dairy-free BeeSop sorbet, a flavor influenced by the West African hibiscus-based beverage, or heat things up with their Hot Banana flavor featuring Sav’s habanero sauce.

15 of 15

Bring Home a Racehorse

At New Vocations Racehorse Adoption Program, couples can volunteer to help out on the farm for the day and discover what life after the track looks like for retired racehorses. Founded in 1992, New Vocations is the nation's premier racehorse rehoming organization—if you happen to fall in love with one of these gentle giants and you can qualify as an applicant, you can become proud parents to one of the New Vocations adoptees.

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