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One day in Lexington, Kentucky

Campbell House exterior with horse sculpture

When Jake and I drove through Louisville and Mammoth Caves National Park as part of a road trip this summer, everyone asked us if we were stopping in Lexington. The inquiries quickly put this city on our-to list and it became another stop we knew we’d try to make on our moving road trip out of Washington, D.C. if we could. Even though it ended up taking us out of the way, we agreed it was well worth the detour! Here’s a mini Lexington Kentucky travel guide to some of our favorite spots.

Lexington, Kentucky
November, 2018


We drove to Lexington from Columbus, which was a quick and easy (all-interstate) three-hour drive. 

Red-brick building and foliage


We stayed the night at the Campbell House, which is part of Hilton’s Curio Collection. As someone who generally tries to stay in places where I can earn and redeem hotel points, I love the Curio brand. Each hotel is different and reflects its location through little details, such as design touches and locally made toiletries. Many of them are also historic (like this one I stayed at in Roanoke, Virginia over the summer). It’s something I really appreciate, especially considering that most hotel chain properties are pretty devoid of character. 

Campbell House hotel room bed
Campbell House hotel room mirror
Campbell House hotel room armchair
Campbell House hotel room desk


Our first stop in Lexington was The Barn, a food hall that houses a number of different kiosks. I was hoping it would be a barn on a farm, and it’s actually a barn at the mall, but the food inside is great nonetheless! I recommend Athenian Grill there, which had some of the best fast Greek food I’ve ever had.

There’s also a location of Crank & Boom inside, which again, is some of the best ice cream I think I’ve ever had in my life. We didn’t try this location—we got it in the Distillery District instead—but just make sure you get it. I had a combination of the Bourbon & Honey and the Kentucky Blackberry & Buttermilk and it was SO GOOD.

After that (yes, I often eat two lunches when trying to explore a new city in limited time… it’s fine) we headed to Red State to meet a grad school friend for barbecue. It’s a hole in the wall and one of those places that’s clearly very popular with locals. I can’t speak to the barbecue myself as a vegetarian, but Jake loved it, and I can confirm that the sides were good!

For dinner, we chose a spot from Ouita Michel, Lexington’s best-known chef. Holly Hill is the flagship, but we opted to try the lower-key Honeywood instead, and while some things were great, others were just okay. I’d try one of her other restaurants if you’re in the area.

The Barn food hall exterior
The Barn food hall interior
Red State Barbecue food
Crank & Boom interior


There were a lot of things we wanted to see in Lexington that we couldn’t for one reason or another, but we did get to explore the Distillery District, an up-and-coming area that sits northwest of downtown. It’s home to a historic distillery building and plenty of street art, as well as two working distilleries and more. 

We enjoyed strolling around downtown and seeing the colorful buildings around the intersection of Main and S. Broadway, and from there we roamed around Gratz Park and the historic red-brick houses near Transylvania University. 

Our last stop before it got dark was Ashland, the former estate of Kentucky politician Henry Clay. We didn’t tour the inside, opting instead to spend time in the gardens (which I’m sure are even prettier when it’s not November). On the flip side, it was the perfect time of year to see the gingko trees on nearby Catalpa St. in full color. 

Henry Clay Estate garden flowers
Henry Clay Estate garden
Henry Clay Estate exterior
Pepper Distillery exterior
Lexington Distillery District street art


Lexington is one of those places that it helps to have a plan for; we couldn’t do a lot of things we wanted to do because it wasn’t the right time, season or day of the week. So if any of these experiences sound like ones you’d be interested in, be sure to check opening hours and making bookings in advance where appropriate. 

Lexington is obviously famous for its connection to horses and horse racing, and there are a few different farms and museums you can visit to learn more about that connection. In particular, as an animal lover, I would have really liked to have visited Old Friends Thoroughbred Retirement Farms, which provides a home and care for retired and rescued horses (as well as offering 90-minute walking tours). The Kentucky Derby Museum also does tours of Churchill Downs, and you can find a slew of other horse farm visit options at this website.  

Lexington’s other big claim to fame is whiskey, and it’s in striking distance of the Bourbon Trail. I’ve toured Buffalo Trace, which I highly recommend—they sell this whiskey cream there that’s basically Bailey’s but with bourbon and it’s SO GOOD—and I would love to go back someday. In town, Town Branch Distillery offers tours, too.

Other places and sights that friends recommended that I want to try next time: Kentucky Native, West Main Crafting Co., Lexington Cemetery, and the art museum at University of Kentucky.

Downtown Lexington shops


My goal for this trip was to do all of our paid stays (a.k.a. not with family or friends) on points. Typically, I try to save points for higher-end experiences that I wouldn’t be able to afford otherwise (and pay for cheaper stays with money to earn points). But considering all the expenses involved with moving across the country, we figured this was as good a time as any to cash in on the 600,000-plus Hilton points I had racked up throughout the year. We redeemed 35,000 Hilton Honors points for a night at the Campbell House, which felt super reasonable given how nice the hotel was (generally, the cheapest Hilton redemptions I find come in around 28,000 points). I’m sure the fact that it was a November weekday had something to do with it, but my guess is that this property has pretty reasonable award rates throughout the year!

Campbell House hotel exterior
Campbell House hotel lobby

For more on earning and using points and miles to travel for free, visit the 52 Cities free resource library or register to join me on my next live masterclass. And for more on my cross-country road trip, check out this post, which has links to posts from every stop!

Hope you enjoyed this mini Lexington Kentucky travel guide! Have you been to Lexington? What did I miss? Let me know in the comments! >>

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December 14, 2018



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