10 Unique Date Ideas in Lexington, KY

You already know all of the standard options for date nights in Lexington…catch a UK game, grab dinner & ice cream at the Distillery District, see a movie at the Kentucky Theatre. And while all of these are GREAT options, hidden beneath the surface of this small city is a plethora of date night (or friends’ night!) options for a night on the town…as long as you know where to look.

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Build your Own Art at a Glass Blowing Experience

Have you ever been to a place with an immersive art experience, cocktail lounge, AND art gallery all in one? Welcome to Trifecta! Book a hands-on workshop to learn the ropes of glassmaking while designing and creating your own unique art piece. This experience is beginner-friendly so no prior knowledge of glassmaking is required! Plus, you can swing by their cocktail lounge afterward to round out the night with a delicious cocktail.

Book an Experience with Trifecta Glass Art Lounge

*This link is an affiliate link, which means we may earn a small commission if you choose to book at no additional cost to you.

Hide Away at a Prohibition-Style Speakeasy

Did you know that Lexington is home to an ACTUAL prohibition-style speakeasy? When you walk through the doors of Constitution’s small stone entrance, you’re immediately transported back in time. Surrounded by bookshelves, you ring a bell for service…but it’s not a small, old bookstore that you’re looking for. Suddenly the shelf in front of you begins to swivel and you’re beckoned inside to try the delicious drinks that await in this hidden cocktail lounge (that also serves non-alcoholic options!). Reservations are recommended, though they do accept a small number of walk-ins, as well.

Constitution Rare & Unique Books (AKA Cocktail Lounge)

Sip & Eat on a Food & Cocktail Tour

This 2.5 hour tour through the East End of Lexington explores the city’s local lore while also offering guests the chance to try some of the best foods and drinks that Lexington has to offer. It includes a visit to one of our all-time FAVORITE Lex restaurants & winds through one of the city’s most up-and-coming foodie districts. The tour is accessible to wheelchair users & it meets at Lucia’s World Emporium (a super cute fair trade shop!).

Bites of the Bluegrass: Cocktails & Bites Tour

*This link is an affiliate link, which means we may earn a small commission if you choose to book at no additional cost to you.

Make Your Own Coffee & Donut Trail

Lexington’s per capita rate of coffee shops AND donut shops makes it VERY difficult for us to consider moving out of the area! Pick a few local shops & build your own Lexington coffee & donut trail in order to determine which cup of caffeine & delectable pastry is best. Whether you’re looking for the best cup of black coffee, cold brew, or signature drink, you’re certain to find a local favorite to pair with your sugary donut. Bonus points if you’re looking for a date night during August when the annual Cold Brew Festival takes place.

Visit our coffee guide to check out some of our Lexington favorites

Our personal favorite donut shops are North Lime Coffee & Donuts & Spalding’s!

Visit the Prismatic Spring at McConnell Springs

On the edge of downtown, tucked in between industrial buildings, is McConnell Springs park, a 26-acre preserve that serves as an underrated oasis for those looking to get away from the hustle & bustle of Lexington’s massive metropolis (lol…I kid, I kid). In all seriousness, McConnell Springs is our favorite spot to quickly tuck into nature without driving out to Raven’s Run or Red River Gorge.

The park is home to a 250-yr-old Bur Oak that towers above the landscape, as well as multiple springs including the prismatic Blue Hole. There are plenty of wildlife to spot at McConnell Springs & our summer routine is that the person to spot the most turtles at the pond is treated to a delicious cup of ice cream at nearby Crank & Boom (the person to spot the least number of turtles is also treated to ice cream so it’s a win-win).

Pick Your Own Apples & Flowers at a Nearby Orchard

Within just a few miles of Lexington are two large orchards with various activities throughout the Spring, Summer, & Fall! While both of these farms are technically in another town, they both rest on the cusp of the Fayette County limits, making them a quick drive from downtown Lexington.

At Evan’s Orchard in Georgetown, you can pick blueberries in June, visit the sunflower fields during golden hour in August, and pick apples & pumpkins in the orchard during the Fall! Through all 3 seasons, you can drink delicious cider, order food from their market, visit the Highland Cows in the petting zoo, and venture through the beautiful grounds.

At Eckert’s Family Farms in Versailles, you can book a private bonfire site, pick seasonal fruits & vegetables, and grab delicious baked goods from the bakery in the Orchard Market.

Visit Lexington’s Oddities

Looking for a more obscure date idea? Check out one of Lexington’s more eccentric sites, including:

Cocaine Bear - Yes, it’s true. Lexington is home to THE Cocaine Bear of the 2023 movie’s fame. The lore is that an American black bear was killed after consuming too many illicit substances that were dropped by a Lexington police officer turned drug smuggler who dropped his cargo over the forests of Eastern Tennesses. You can pay your respects to “Pablo Escobear” at the Kentucky Fun Mall, where you can also check out a quirky variety of Kentucky-themed gifts.

Lexington Dixie Cup Water Tower - The name says it all. This water tower is shaped like a Dixie Cup. Though Dixie Cups are no longer in production in Lexington, LEX airport uses it as a point of reference, so the city refuses to remove it.

Moosnick Medical Museum (temporarily closed) - Arguable the strangest item on this list, this unique museum on Transylvania University’s campus is home to sky meat (yes…meat that mysteriously fell from the sky), an extremely large hairball that was extracted from a cow’s stomach, and more than a couple actual skeletons. It’s temporarily closed during building renovations, but worth checking out once it reopens if you can stomach the museum’s contents!

You can also check out one of the local oddities shops at Pop’s Resale & SQecial Media!

Take a Cooking Class

What’s better than a hands-on experience learning from local chefs and cooking a meal that is guaranteed to be delicious (regardless of your personal cooking skills)? Luckily, Lexington has multiple cooking class options!

Lexington Pasta Garage, known for its incredible handmade pasta, offers regular pasta-making classes complete with appetizers, drinks, and dessert! Classes are offered multiple days each month and you take home three pounds of freshly made pasta with you.

La Bonne Vie offers a wide variety of cooking classes for all different taste preferences & dietary needs! From seasonal baking to dishes from around the world to Appalachian staples, you’re bound to find the perfect date night to bond over cooking a delicious meal.

Go for a Climb at LEF Climbing Gym

Whether you’re seeking to show off your athleticism or learn a new skill, Lexington’s local climbing gym is the perfect place for a fun night out. LEF offers day use passes that allow you to climb until closing time at 9pm. All climbing equipment is included, along with an orientation to the facility & the auto-belay, making this accessible for new climbers, as well as seasoned ones!

Book a Day Pass to LEF here

Join an Elaborate Tasting Event at Omage

Admittedly, this is the most expensive option on this list, but if you’re looking for a truly out-of-this-world experience in the heart of downtown Lexington, an Omage event is the perfect option. Their themed parties feature amazing multi-course dinner & drink menus with elaborate decorations that immediately transport you out of Lexington and directly into the vacation destination of your dreams. For a top-notch experience to celebrate a big occasion, consider booking tickets to an Omage event at the Apiary!

Book an Omage event at the Apiary here