A Weekend in: Lexington, KY

For my travelers out there, I’m testing out a new series I’ll try to keep up with each week. I love to travel, and my jobs lately have kept me traveling the country quite a bit so I’ve gotten to see a lot of cool cities and hear about what makes them all special and unique. I’m planning to highlight what each city I’ve been to has to offer for out-of-towners (as well as locals!) to get a taste of the city’s culture and environment.

What better city to start with than my new home, Lexington, Kentucky?! I’ve officially lived here for three months today, and I’ve never felt more at home anywhere I’ve lived. Rent is affordable, people are beyond friendly, and the scenery is absolutely breathtaking. I’m not lying when I say I can drive from my apartment to work and the barn without a single stoplight, and I don’t even live in a rural area! I pass lush green rolling hills dotted with horses (and foals!) my whole way there and the awe still hasn’t faded.

So next time you’re looking to plan a fun weekend away, or meet up with old friends for a reunion somewhere fun and affordable, definitely consider Lexington! I’ll provide a fun weekend itinerary for what to do in the fall, and of course I’ll share more options down the road once the seasons start to change!


Where to Stay

The Campbell House offers stylish masculine interiors with spacious and comfortable rooms situated in a location close enough to downtown shops and restaurants, but still off the beaten path in a quieter neighborhood.

Airbnb is a great option in Lexington, as well. There are lots of charming homes right outside the downtown area that have been divided into smaller units that the owners rent out to visitors. This allows you to walk to the spots downtown and be out of the hustle and bustle of the city streets.

The 21C Hotel is hard to beat, accommodation-wise. The rooms are stylish and comfortable with artwork all over the hotel. It’s also conveniently located in the heart of downtown, so location can’t be beat.


Friday Evening

Drinks & dinner: OBC Kitchen and Bar is designed to feel like a bourbon distillery, and has a grand drink menu to go along with that feel. The food is also superior quality without being stuffy or fancy. It’s a great place to spend the first night while everyone is just getting settled and beginning to plan the rest of the weekend. If the weather is nice there’s a small patio, but it’s also great on cooler nights to feel tucked away in its cozy atmosphere. The bar is also a stunning sight to see.


After dinner: The best ice cream in Lexington is definitely Crank & Boom, which has several locations and a variety of ice cream flavors that will satisfy anyone’s tastes. Definitely go to the location in the Distillery District so you can hit up some bars to see what Lexington’s unique nightlife has to offer!



Breakfast: A quick bite is what you’ll want on a Saturday morning because you’ve got somewhere important to be. Magee’s Bakery is a family-owned and operated hotspot conveniently located downtown that will fill you up and get you on your way to the main event. They’ve got all sorts of baked goods from donuts to pies and also feature a menu with breakfast sandwiches and omelets.

Morning activity: October in Lexington is ALL about Keeneland. General admission is only around $5, so grab your best sundresses and hats and go spend the morning at the racetrack!

Lunch: Corto Lima is a fresh spin on Latin American food and claims to have Lexington’s best margarita (I’ll let Jay Bilas be the judge of that). It’s got a fun and whimsical interior with tables outside on a cute downtown street corner.

Happy hour: Lexington is home to a unique hotel experience, the 21C Hotel and Museum. This small hotel chain features intriguing and inspiring art galleries you can wander through as well as an innovative restaurant and bar. Lockbox is a great spot to grab a craft cocktail or glass of wine and reflect on the interesting art throughout the space.

A perfectly plated entree at Carson’s

A perfectly plated entree at Carson’s

Dinner: Carson’s Food and Drink offers arguably the best dining experience in downtown Lexington. It’s in a charming little house right in the city, and the food is to die for. Have a reservation just in case, but Lexington restaurants are never super busy. They describe themselves as “a rustic, yet refined concept with chef-driven recipes paired with prohibition cocktails, hand-selected wines, and craft beers.” This is a restaurant you can get a little more dressed up for, but it’s still not stuffy in any way, so you can dress casually, as well.

Holly Hill Inn’s Bluegrass Benedict

Holly Hill Inn’s Bluegrass Benedict


Brunch: Holly Hill Inn features a “Bluegrass Brunch” in the fall that’s not to be missed. The menu features items like Crepes Monsieur and Chocolate Bourbon Pecan Pie.

Morning activity: You can’t visit horse country without taking an obligatory tour of a thoroughbred farm. Unlike most cities, horses are only a stone’s throw from the city, so it’s easy to get out to one of these stunning farms and see some famous retired racehorses. The operations they run are impressive, and the facilities are often are nicer than most homes. The famous Claiborne Farm offers weekend tours in the mornings, but be sure to check out VisitHorseCountry.com for more special deals and unique visits at other farms, too.

An entrance to Claiborne Farm, where Secretariat lived out his retired years and is now buried.

An entrance to Claiborne Farm, where Secretariat lived out his retired years and is now buried.

Lunch: Once you’re out in horse country, you won’t ever want to come back to city life. But there’s still so much to offer out that way! Windy Corner Market is the next mandatory stop on the list before you leave town. They’ve got a delicious menu with breakfast offered all day, along with lunch and dinner options. This is also a great place to pick up some souvenirs; they’ve got lots of local food items as well as locally designed goods and gifts!

Afternoon activity: If you’ve still got a thirst for more, spend the final afternoon at Woodford Reserve for a bourbon tasting experience like no other. It’s located in the stunning Woodford County and is a lovely fall outdoor activity while tasting bourbon and hanging out with friends and/or family. Plus, it will have you very relaxed just in time to head to the airport to fly out! Highlight of flying out of Lexington is the ease of getting through the airport. No need to arrive more than 45 minutes before your flight takes off!


If you know of any great Lexington spots you’d like to let me know about, please send me a message! I haven’t been to all of the places listed here, but through all my friends I’ve heard wonderful things about the places I haven’t gotten to yet. I’m always looking for more tips to get to know my new city even better!

Tori BilasComment