72 Hours in Lexington, Kentucky

A very dear friend of mine was married at Keeneland in Lexington, Kentucky. We were excited to make the trip to celebrate her wedding (IRL!!) and witness their marriage. There is something about weddings. Love is so good y’all.

Justin had visited Keeneland once before — 20 years ago — so needless to say, this trip was quite different than the one before, but with about 36 hours outside of the wedding, we took the opportunity to explore all that Lexington had to offer. And a major bonus: one of Justin’s college friends lives just outside of the city and showed us around for a couple of hours.

FRIDAY

We arrived on Friday late afternoon. Finding rideshare was impossible but we snagged a taxi. Bring cash just in case.

The main hotel block was at the Marriott City Center which was where we stayed. The hotel is BRAND NEW and literally in the city’s center. It’s connected to a Residence Inn as well. We were hungry so we went up to the rooftop bar to grab a bite and a drink. The pool and bar is in the Residence Inn (just FYI). Food was simple and what you’d expect of a hotel kitchen — I had a Caesar salad and Justin had the burger. The drink selection was strong — great local beers and cocktails on tap.

That night we checked out not one, not two, not three, but FOUR places. Let’s just say we were happy to be out of the house.

We started at Lockbox, which is located across the street at boutique hotel 21c. It was an awesome, art-filled, funky spot. I ordered a gin drink and Justin a take on a Manhattan. We shared the potatoes as the menu was kind of small. Cocktails were excellent and balanced well.

Next, we went across the street to “the Grove,” and couldn’t find a seat outside but sat inside at Harvey’s which boasts a sexy, dark vibe with deep wing back chairs and single booths. I felt like we were in London. We snagged a snack of cheese from Fable which is located inside Harvey’s.

We had welcome drinks for the wedding at Mane on Main, which is a private venue on like the 15th floor of the chase building. Great views if you are in need of a location that can hold a crew!

Finally, leaving welcome drinks I was ready for a bit more food, and knowing there was a steakhouse next to the hotel I said let’s just go there.

Classic steakhouse flex: the celebrity gallery wall

Now, Justin has been to nearly every steakhouse in America. 10+ years of corporate business travel will do that. So, his expectations of them are ... well another post for another day. But Jeff Ruby’s y’all. Jeff Ruby’s. This was next level. Part steakhouse. Part sushi house. Part jazz house. It was a mix of New Orleans and Las Vegas...smack dab in the middle of Lexington, Kentucky. I could have sat there all day and night. I was the happiest human. We sat at the bar (we are bar people) and had a couple of drinks and some sushi. It was spectacular...and Justin agreed.

SATURDAY

On the day of the wedding, we had most of the day to explore.

We met up with Justin’s fraternity brother and had breakfast at Carson’s. It was a short walk from the hotel but it was such a gem. Inside/outside seating, and very charming, this spot served an awesome brunch. I had the vegetarian bowl and a side of bacon. I know. But like ... #prioritizeprotein, y’all.

We walked around town for the next hour, exploring streets and learning a little about the history of Lexington as well as spots to hit up if time allowed.

We snuck into the Keeneland Mercantile to snag an ornament as we do for many of our trips. While this wasn’t a “vacation” in the traditional sense, it felt like one with having time to explore and meet up with a local.

On the quest for a Cobb salad, we checked out The Thirsty Fox at Zim’s and Zim’s Café. They are separate areas – The Thirsty Fox had a fabulous cocktail list and all of the bourbon you can imagine, but knowing the night ahead, I settled on a French75. I loved the Cobb salad. You can read about that (and other Cobb salads!) here.

After a quick nap, it was time to get black tie ready. Could my feet handle heels after a year+ of sneakers? (Spoiler: barely, but we did) The wedding was magnificent - situated on the impeccable grounds of Keeneland. Beautiful barn with large beams, a great indoor/outdoor venue and live music kept us singing along all night. Congratulations, again to Brigid and Zach, we love you both!!

After the party’s the after-party and we went to McCarthy’s, an Irish dive bar, for a drink.

SUNDAY

Walked to Horse & Jockey for the wedding brunch. Fruit, potatoes, eggs, sausage, and a mimosa later, I was feeling decent, albeit the red recovery on Whoop. I decided to track my day to the best of my ability, knowing I had a trip on the other side of this weekend.

Post brunch and hugs goodbye, we grabbed coffees from the funky-feel good Third Street Stuff and then made our way back to the hotel to sneak in another quick nap.

I convinced my husband to run down to Corto y Lima. We walked by this spot two or three times and the chips and salsa called my name each time. I was hungry and decided to chance this quick Latin lunch instead of eating airport food. And WOW so glad we did y’all. It was the perfect ending to our trip. The chips and salsa trio delivered, and I ordered the tamales. Filled with pork they were the perfect protein and carb option for me. Justin had the steak tacos which were small/street style so we had the best “we need food but like maybe not a full meal-meal.” It was a quick meal, and an absolute must on your travel day (or at least at another time). This spot was the absolute most darling, cute spot you’d expect in some major city.