Known for its storied horse farms and Southern charm, Lexington, Kentucky is full of hidden gems and unique local finds waiting to be explored. Beyond the thoroughbreds and bourbon tours, Kentucky’s second largest city offers many romantic activities for couples.
| Romantic Activity | Description |
|---|---|
| Sunset Stroll Through Historic Downtown | Enjoy a romantic evening walk among vintage architecture, indie boutiques, and restaurants. |
| Sip Local Wine at a Vineyard | Tour picturesque vineyards and sample Kentucky’s signature wines. |
| Cheer on Horses at Keeneland Race Course | Experience live horse racing and Southern hospitality. |
| Browse Farmer’s Market in Chevy Chase | Explore local produce, baked goods, and enjoy a brunch in a charming setting. |
| Tour Horse Farms | Visit majestic horse farms and meet Kentucky Derby winners. |
| Enjoy Southern Comfort Food | Dine at upscale or casual local restaurants offering authentic Kentucky cuisine. |
| Take a Cooking Class Together | Participate in a couple’s cooking class to prepare seasonal dishes. |
| See a Show at Lexington Opera House | Enjoy an evening at the elegant performance hall with various shows. |
| Hike or Bike the Woodland Trails | Explore scenic trails, perfect for hiking or biking. |
| Relax at Spas & Baths | Indulge in relaxing spa treatments and baths. |
| Go on a Bourbon Distillery Tour | Learn about bourbon crafting and sample straight from the barrel. |
| Admire Art at Local Galleries and Studios | Explore Lexington’s local arts scene and meet artists. |
| Catch a Film at the Historic Kentucky Theater | Enjoy a classic movie in an elegant Art Deco movie palace. |
From scenic countryside drives to quaint cafés and cultural attractions, Lexington has something to spark every pair’s passions. Here are the top 12 romantic things to do in Lexington:
Take a Sunset Stroll Through Historic Downtown
Name and Location: Historic downtown Lexington, centered around Main Street and adjacent blocks.
History and Significance: Lexington’s downtown features restored 19th century buildings housing boutiques, galleries, and restaurants. Many structures date back before the Civil War. Strolling downtown around sunset takes in the charming architecture.
What to Expect: Leisurely walks along brick sidewalks beneath glowing lampposts. Picturesque storefronts and quaint alleys to explore. Street performers and musicians may provide entertainment on weekends.
Visitor Information: The downtown area is compact and walkable. Free two-hour parking is available on many streets.
Lexington’s downtown district features vintage architecture, indie boutiques and hip restaurants housed in historic buildings. Take a romantic evening walk down East Main Street, West Main Street and North Limestone to admire the 19th century architecture lit up at dusk. Stop to share sweet treats from chocolate shops and bakeries along the way.
Pop into antiquing stores like Lexington Vintage Clothing or Double Take Retro to find hidden treasures. For more shopping and dining options, visit Victorian buildings like the Lexington Financial Center and The Square.
Sip Local Wine at a Vineyard
Name and Location: Kentucky’s wine country in and around Lexington, including Proterra Winery, Grimes Mill Winery, Talon Winery, and more.
History and Significance: Kentucky has a growing wine industry, producing high-quality vintages from grapes grown locally in the state. Winery tasting rooms offer a chance to savor regional varieties.
What to Expect: Wineries have rustic tasting rooms and outdoor patios where you can sample red, white, and blush wines. Most offer tours of their vineyards and production facilities. Light snacks or meals may be available.
Visitor Information: Wineries are open daily year-round. Free tastings are offered, some require reservations. Hours vary by location.
The Bluegrass region has a fast-growing wine industry, with over 60 wineries in the Lexington area. Spend a day touring picturesque vineyards and sampling Kentucky’s signature wines. Enjoy intimate tastings at award-winning spots like Jean Farris Winery, James E. Pepper Distillery and Talon Winery & Vineyards. Many offer live music and food pairings in their tasting rooms set amidst rolling vineyards. Relax together on the outdoor patios with a bottle of red or white.
Cheer on the Horses at Keeneland Race Course
Name and Location: Keeneland Race Course, located on Versailles Road west of Lexington.
History and Significance: Keeneland first opened in 1936 and is renowned for its beautiful setting and elite Thoroughbred racing. Live racing meets are held in April and October, with races simulcast year-round.
What to Expect: An exciting atmosphere watching majestic horses compete on the track. Betting windows and beginner betting tips available. Reserved seating, general admission, dining, and event spaces on site.
Visitor Information: Free general admission on non-reserved seat days. Paid parking on site.
A trip to Lexington isn’t complete without experiencing the thrill of live horse racing at beautiful Keeneland Race Course. Open only for races in the spring and fall, Keeneland offers action-packed racing and refined Southern hospitality. Watch champion thoroughbreds compete from under the Grandstand or trackside. Wager on races together for a chance to cheer your pick on to the finish line. Stick around for live music and dancing on Friday nights.
Browse the Farmer’s Market in Chevy Chase
Name and Location: The Chevy Chase Farmer’s Market takes place along Euclid Avenue in the Chevy Chase neighborhood of Lexington.
History and Significance: Founded in 2008, this seasonal market allows visitors to buy local produce, meats, baked goods and crafts directly from area farmers and artisans.
What to Expect: Farm-fresh fruits, vegetables, eggs, meats, cheeses, flowers and plants for sale from over 50 regional vendors. Local artisans also offer crafts, jewelry, soaps and more. Family-friendly atmosphere.
Visitor Information: Held Saturdays 8am-12pm from May to October. Located on Euclid between High and Woodland. Free admission and parking.
For fresh local finds in an artsy setting, visit the Chevy Chase Farmer’s Market on Saturdays. Stroll from vendor to vendor sampling apples, produce, baked goods, honey, flowers and more. After filling your tote bags, stop for brunch on the patio at Coba Cocina. Check out the street art and murals around the shops. Then walk hand-in-hand taking in neighborhood sights.
Tour Horse Farms
Name and Location: Horse country surrounding Lexington, including farms in surrounding towns like Versailles, Midway, and Paris.
History and Significance: The Bluegrass Region is world-renowned for breeding champion racehorses and show horses. Farms are devoted to breeding, training, and promoting Kentucky’s equine heritage.
What to Expect: Guided tours showcase elite horses and facilities. Visitors gain insight into horse care, training, and Lexington’s special relationship with horses. Reservations required.
Visitor Information: Group tours by reservation. Recommended farms include Coolmore, Juddmonte, and WinStar. Fees and hours vary by location.
No trip to Lexington is complete without visiting majestic horse farms, many open for tours. At Dell Hancock Farm, meet past Kentucky Derby winners in the stable and pet retired champion stallions roaming in the paddocks. Watch skilled farmhands work with foals and mares at McConnell Springs Farm. For homegrown hospitality, opt for a private carriage tour of Calumet Farm or Winstar Farm.
Enjoy Southern Comfort Food at a Local Restaurant
Name and Location: Lexington’s top spots for Southern and regional fare include Honeywood, Dudley’s on Short, Carson’s Food & Drink, and more.
History and Significance: Lexington restaurants are known for artfully reinventing Kentucky and Southern classics using fresh, local ingredients. The city’s food scene balances tradition with contemporary flair.
What to Expect: Creative takes on fried chicken, collard greens, biscuits, burgoo stew, bourbon cocktails, Benedictine sandwiches, derby pie and more Southern flavors. Relaxed but sophisticated settings.
Visitor Information: Many options located downtown or in surrounding neighborhoods. Make reservations for popular dinner spots. Locally-owned eateries highlight regional strengths.
Lexington’s diverse food scene offers everything from haute cuisine to hole-in-the-wall joints serving authentic Kentucky favorites. For upscale Southern dining, book a table at Honeywood or Dudley’s on Short – located in a converted Victorian home. Keep things casual with biscuits & fried chicken at County Club or bourbon slushies and live music at Al’s Bar. Wherever you dine, savor Southern staples done right.
Take a Cooking Class Together
Name and Location: Hands-on cooking classes offered by local chefs at venues like Fork & Knife Cooking School, Bluegrass Kitchen, and others.
History and Significance: Lexington’s cooking classes allow participants to gain skills and recipes for preparing regional specialties under expert guidance. A fun couple’s activity.
What to Expect: Instruction in hands-on cooking techniques, often with a multi-course meal enjoyed afterward. Classes may cover topics like Southern basics, baking, barbecue, sushi rolling, and more.
Visitor Information: Classes generally 2-3 hours long for groups up to 20 people. Reservations required. Skill levels from beginner to advanced offered.
For an interactive date, book a couple’s cooking class through FoodChain Lexington. Work side by side to prepare seasonal vegetarian dishes under the guidance of chef professionals. Classes take place in their bright sunny teaching kitchen stocked with local ingredients. You’ll make memories cooking together – and enjoy the fruits of your labor for dinner! They also offer hands-on date nights making pizza, pasta and Latin dishes.
See a Show at Lexington Opera House
Name and Location: The Lexington Opera House is located on East Short Street in downtown Lexington.
History and Significance: This historic performing arts venue opened in 1886. Completely restored in the 1970s, the Opera House now hosts touring Broadway shows, concerts, plays, and local performances.
What to Expect: Elegant Victorian theater interior. Performances range from Broadway musicals to comedy acts, symphonies, and more. Drinks and snacks available during shows.
Visitor Information: Located at 401 W Short St. Box office hours Monday-Friday 10am-5pm.
All dolled up for a glamorous evening out? Take in a Broadway musical, ballet or opera at the vintage Lexington Opera House. This elegant performance hall has entertained Lexington since 1886. Cuddle in the vintage red velvet seats before being whisked away by the performers’ artistry. Surprise your partner with tickets to their favorite show for an extra magical date night.
Hike or Bike the Woodland Trails
Name and Location: The Woodland Trails are located in the Masterson Station Park area of northeast Lexington.
History and Significance: Winding through forest and meadows, these scenic trails opened in 2008 on a former horse farm. They’re popular for hiking, trail running, mountain biking and horseback riding.
What to Expect: Over 15 miles of picturesque wooded trails with gentle climbs and creek crossings. Benches along the way offer spots to rest. The park has an archery range and dog park.
Visitor Information: Located at 3501 Leestown Rd. Open daily dawn to dusk. No admission fee. Parking available at the trailhead.
Pedal together along Lexington’s scenic bike trails running through woodlands, wetlands and parks. Rent a tandem bike and cruise the Shillito Park Trail hand-in-hand. Mountain bike at Veterans Park or hike amid wildflowers at Raven Run Nature Sanctuary. Pack a picnic and refreshments to enjoy after working up an appetite on the trails.
Relax at Spas & Baths
Name and Location: Luxury spas in Lexington include the Spa at Lexington Griffin Gate, the Woodhouse Day Spa, and the Spa on Maxwell.
History and Significance: Lexington’s spas offer rejuvenating massages, facials, body treatments, and relaxation experiences in serene settings. They incorporate regional influences like bourbon, horse themes, and natural Kentucky elements.
What to Expect: Pampering services include massages, body scrubs, wraps, facials, manicures and more. Spas have elaborate indoor and outdoor treatment areas, pools, and lounges.
Visitor Information: Located at high-end hotels and dedicated spa facilities. Reservations required for treatments. Packages available.
Treat yourselves to a relaxing couples spa session in Lexington. Get massages side-by-side at Well & Being Spa, followed by sitting in the tranquil sanctuary room together sipping herbal tea. Unwind in the thermal pools and saunas at 21c Museum Hotel Spa, or book private outdoor soaking tubs at Belle Notte Luxury Collective.
Go on a Bourbon Distillery Tour
Name and Location: Bourbon distillery tours offered in Central Kentucky near Lexington, including at Woodford Reserve, Wild Turkey, and Town Branch.
History and Significance: Kentucky produces 95% of the world’s bourbon. Tours showcase the heritage and production process behind the state’s iconic spirit. Most are on historic properties.
What to Expect: Behind-the-scenes tours of facilities including mash houses, stills, warehouses and bottling lines. Tastings of premium bourbons often included. Gift shops on site.
Visitor Information: Tours range from $10-35 per person. Dates and times vary by distillery. Reservations recommended, some required.
No trip to Kentucky is complete without visiting a legendary bourbon distillery. Learn about the historic process of crafting bourbon on tours of Buffalo Trace and Town Branch Distillery. Taste award-winning bourbon samples straight from the barrel. Some tours even allow you to bottle your own bourbon together as the ultimate personalized souvenir. Savor bourbon cocktails or a tasting flight at the end of your tour.
Admire Art at Local Galleries and Studios
Name and Location: Lexington’s vibrant arts scene is centered in districts like Northside, West Sixth, Distillery, and East End.
History and Significance: Lexington has a thriving arts community encompassing painters, sculptors, photographers, fiber artists, and more. Local galleries provide a showcase for regional talent.
What to Expect: Rotating fine art exhibits in formal gallery settings, as well as open studio events that allow visitors to engage directly with artists.
Visitor Information: Many concentrated in re-emerging neighborhoods. Gallery Hop occurs monthly downtown. Check local event calendars for art openings.
Lexington is home to a thriving local arts scene. Peruse emerging talent at public art gallery spots like Institute 193, Tadoo Lounge and Pam Miller Downtown Arts Center. Meet local artists busy at work during studio tours in the Distillery District. Admire colorful street murals around downtown. Check event calendars for art walks and open gallery nights to mingle with the creative community.
Catch a Film at the Historic Kentucky Theater
Name and Location: The Kentucky Theater is located on Main Street in downtown Lexington.
History and Significance: Built in 1922, this grand movie palace is the last of its kind still operating in Kentucky. Restored in the 1980s, it now shows indie and classic films.
What to Expect: A majestic theater with ornate decor, balconies, and a large screen. Concessions like popcorn, candy and beer/wine served. Occasional live concerts and events.
Visitor Information: Located at 214 E Main St. Movie showtimes Thursday-Sunday. Tickets $7 for general admission.
For an old-fashioned cinema date night, head to the Kentucky Theater downtown. This elegant Art Deco movie palace first opened in 1922, and still shows films today. Sip cocktails in the lounge before entering the grand auditorium adorned with sparkling chandeliers. Catch classic movies or limited-run independent films screened in the historic single-screen theater.
Conclusion
Lexington offers no shortage of opportunities for romantic outings, from thoroughbred racing and pastoral vineyards to historic theaters and Southern cuisine. Get your hearts racing at the racetrack, then relax over a long farm-to-table dinner. Lexington’s fusion of fast horses and Southern charm provides unique date ideas you won’t find anywhere else. Whether your tastes run more active or relaxed, you’ll find many ways to connect and rekindle romance exploring all Lexington has to offer.