Lexington Kentucky A Charming Town Where Daters Enjoy A Quiet Getaway

Men's Dating

Lexington, Kentucky: A Charming Southern Town Where Daters Can See Horses, Sip Bourbon & Enjoy a Quiet Getaway

Amber Brooks

Written by: Amber Brooks

Amber Brooks

Amber Brooks is the Editor-in-Chief at DatingAdvice.com. When she was growing up, her family teased her for being "boy crazy," but she preferred to think of herself as a budding dating and relationship expert. As an English major at the University of Florida, Amber honed her communication skills to write clearly, knowledgeably, and passionately about a variety of subjects. Now with over 1,800 lifestyle articles to her name, Amber brings her tireless wit and relatable experiences to DatingAdvice.com. She has been quoted by the Washington Times, Cosmopolitan, The New York Post, and AskMen.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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The Short Version: Located in the heart of horse country, Lexington, Kentucky, offers a calm respite from big-city life. The charming college town is proud of its local attractions, including a world-famous horse racing facility and a nationally syndicated bluegrass show. Whether you enjoy farm fresh meals or mind-bending shows, Lexington has a little something for everyone, and daters don’t have to spend a lot of money to have a great time together. Couples can take in a show, tour a distillery, visit a farm, or sit down at a locally owned restaurant to spend a relaxing evening in the date-friendly city. Many locals think of Lexington as the front porch of the South because it’s a welcoming place to listen to bluegrass music, savor a glass of bourbon, and enjoy other activities rooted in Southern tradition and American values.

When I come home to visit my parents for a weekend, one of the first things I ask is, “What do we have to watch together?” They keep a lengthy DVR list of old and new shows to watch as a family. Once we’ve dispensed with our must-watch list, my dad will invariably try to get hold of the remote and put on a country-bluegrass music show called “WoodSongs” before anyone can object.

Hosted by folk singer Michael Johnathon, “WoodSongs” showcases the musical talents of singers, fiddlers, cellists, and folk bands in an old-time radio show broadcasted on TV from Lexington, Kentucky. The show reminds my dad of his parents’ bluegrass roots, and he’s awed by many of the performances. Sometimes he’ll get out his own guitar and strum along to his favorite songs, trying to replicate the complex chord progressions.

Photo of a WoodSongs show

Lexington’s “WoodSongs” gives its stage to many contemporary and old-school bluegrass musicians.

My dad would love the chance to go to a “WoodSongs” show in person and listen to the twangy tunes live. That’s a musical treat many Lexington residents take advantage of on Monday nights. “WoodSongs” hosts about 40 live shows a year at the Lyric Theater in Lexington. Admission is free, and hundreds of locals attend regularly. The talent lineup changes every week, but the performances always celebrate the grassroots music of the American South.

Niki Heichelbech-Goldey, the Director of Communications at Lexington, told us she and her husband often make a date night of going to a “WoodSongs” show and eating out at a restaurant afterward.

Lexington offers residents and visitors many engaging and off-the-beaten path date options to help couples have a romantic time in quaint local venues. “We’re a small, liberal destination with a lot of energy,” Niki said, “because we’re also a college town with over 35,000 students and graduates at the University of Kentucky.”

Take Your Riding Partner to Farm Tours & Equestrian Sports

Lexington is widely considered the horse capital of the world because of its large concentration of horse ranches, thoroughbred racing facilities, and other equestrian attractions. The well-known Keeneland Race Course offers visitors a day of fun activities watching races, touring the stables, and relishing the company of local horse lovers. You can see the excitement on many faces as they wait for the next race. During the biannual meets in April and October, thousands of people come dressed to impress and looking forward to a fun afternoon. Admission can cost as little as $5, so this is a date activity that won’t break the bank — which makes it popular among university students.

Throughout the year, many farms and horse ranches open their doors to the public and invite people to look at the healthy horses in the field. Just down the road from Keeneland, Mill Ridge Farm shows off its thoroughbred racing champions and gives visitors a thorough history and background of the family-owned land in a public horse tour.

Photo collage of Mill Ridge Farm's horses and facilities

You and your date can feed carrots to foals, mares, and studs at Mill Ridge Farm.

Niki told us March is the best time to go to a horse ranch because the foals born at the beginning of the year will be active and adorable. “Spring is our baby season,” she said. “It’s fun to be there and see the foals in the field. I love it because of the cuddle factor.”

Whether you want to check out the studs or fawn over a foal, you can book a low-key horse tour at one of Lexington’s many upstanding farms by using Horse Country’s simple search tools. Simply type in a location name and set a range of dates, or you can search by category (stallion, nursery, feed mill, etc.) to find a great opportunity to roam the countryside with someone special.

Horse Country has recently expanded its selections to include a visit to the local horse clinic. Curious couples can book a visit to witness surgeries, live births, and other veterinary services.

When you’re saddling up for a date, you should keep an eye out for popular local events such as the Land Rover Kentucky Three-Day Event. Every April, this equestrian triathlon puts horse and rider through their paces in a series of jaw-dropping shows. People tailgate and cheer, vendors sell their wares, horses show off their agility, and everybody comes away having had a fantastic time. “We call it the best weekend all year,” Niki said. “It’s action-packed all day long.”

Savor Farm Fresh Meals & Barrel-Aged Spirits

Lexington’s large number of locally owned restaurants sets it apart from a lot of other cities. The dining options you’ll find in the city emphasize farm fresh ingredients and good old-fashioned family feeling. You and your date have plenty of savory options to make a romance-infused memory in this city. As Niki said, “Any good date should be all about good food and drink.”

To start with, we have to talk about bourbon. Lexington is famous for its barrel-aged spirits and boasts nine world-famous bourbon distilleries within 35 minutes of the downtown area (aka the bourbon lover’s playground). The Buffalo Trace Distillery is particularly fun for daters because it offers over 3,000 experimental bourbons and a tour of its award-winning facilities. Tours leave every hour on the hour, so you can come any time, grab a drink, and get a behind-the-scenes look at the work that goes into every tasty sip.

Photo of Crank and Boom's specialty items

The Crank and Boom puts a modern spin on classic ice cream treats.

Lexington’s Distillery District is quickly becoming a local hot spot of entertainment and eateries. Couples can easily spend an entire evening dining and drinking here. You can read more about the distilleries here.

In the district, we recommend getting dinner at the Middle Fork Kitchen Bar where couples can split small plates of house-curated cheeses or poached eggs. Then you can walk over to the Crank and Boom Ice Cream Lounge, which serves homemade craft ice cream. You can mix and match up to four signature flavors, and choose to make it a Spiked Scoop — which means adding in a shot of bourbon, amaretto, rum, tequila, cherry liqueur, or other spirits. Plus, the Crank and Boom’s mouth-watering homemade toppings include strawberry sauce, marshmallows, whipped cream, and bacon!

Finally, you can top off your night out with a nightcap at the Break Room, so named because it was once a break room for a local distillery. From the full bar to the fire pit, this cocktail bar provides an intimate place to relax with a date. “We had prompt service at the bar, and they had great tunes going,” said Brian B. in a Yelp review. “Hard to ask for more in a bar.”

Lexington can fill your plate with unforgettable options from the juicy prime cuts at Blue Heron Steakhouse to the hand-tossed pizzas at Goodfellas Pizzeria. Additionally, the Barn is a popular date venue for couples who enjoy authentic Southern dishes. You’ll find this artisan food hall in the Summit at Fritz Farm, an all-local lineup of restaurants and shops

“We’ve been farm-to-table since 1775 when we were founded,” Niki said. “It’s such an agricultural area, the chefs have so many fresh ingredients to work with.”

Listen to Bluegrass Music or Watch an Off-Broadway Show

As the largest public college in the state, the University of Kentucky adds a fair amount of culture and entertainment to Lexington — and singles are always using campus activities to fuel fun and romance. The University of Kentucky Art Museum is open to the public from Tuesday through Sunday. The galleries feature over 4,800 art pieces, including paintings, sculptures, drawings, photographs, and prints — and, best of all, admission is free.

Museums are ideal for daters who want to stimulate conversation and go outside the normal dinner-and-movie routine. The Lexington Opera House is another great place to up your dating game. You can take in a show together and share a unique cultural experience for an affordable price. Audiences rave over the featured performances, which showcase the talents of country music icons, illusionists, ballet companies, and off-Broadway performers.

Photo of the Lexington Opera House

On your next hot date, why not get tickets for a performance at the Lexington Opera House?

On the third Friday of every other month, Lexington’s downtown area comes alive with artistic exhibits during an event known as the LexArts HOP. From 5 p.m. to 8 p.m., thousands of art lovers walk from gallery to gallery to view new art pieces. Over 40 participating locations, including many restaurants and bars, offer free admission and happy-hour prices. The next LexArts HOP event will take place on March 16.

“It’s a festive night to be downtown,” Niki said. “There are a lot of people walking around, looking at art, having dinner, and enjoying an evening out.”

Lexington: The Front Porch of the South Welcomes Visitors

Once you figure out what your loved one likes, you can score major points by planning dates around his or her interests or hobbies. For instance, all it takes to make my dad happy is for my mom to offer to watch “WoodSongs” together. He loves sharing his passion for music with his family and friends, and he jumps on any opportunity to harmonize with my mom.

At Lexington, couples can enjoy bluegrass music, bourbon tastings, and equestrian events together. The Southern city has so many activities and attractions — including baby horses! — to entertain anyone on a date

Whether you prefer eating farm fresh meals, petting horses, or listening to grassroots music, you can delight your senses on a tour of Lexington’s restaurants, farms, stables, or concert halls. No matter where you go, it’s easy to find romance here.

“It’s a really friendly environment,” Niki told us. “It’s a small big town that’s grown a lot over the last few years. Overall, I’d say we’re a charming Southern town with a lot of date night opportunities.”

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