Lexington, Kentucky

OK, mine might be a slightly biased opinion — I currently live in Lexington, KY. But hear me out: As a transplant of this city, I can personally vouch for just how easy a getaway this city is. For one, it’s not difficult to get to: If you’re not driving from a nearby state, there’s a small airport in town you can fly into. Or, you can add a leg onto your trip and book your flight to Cincinnati, which has a bigger airport about an hour away from Lexington (and, to boot, is another cool and very underrated spot for a visit).

It may be more of a large town than an actual city, but what it lacks in size, Lexington makes up for in character. Its claims to fame are unique: Not only is it home to some of the state’s (and world’s) most famous bourbon distilleries — many of which have fun and informative tours — it’s also where the thoroughbred auction house and historic racetrack Keeneland is located. Honestly, you could spend one day touring the Kentucky Bourbon Trail and another at Keeneland’s Fall Meet (which runs from Oct. 6 to the 28th in 2023) watching the horses race, and you’d be set for the weekend. But if you want more, stop in at Kentucky Native Café for a magical afternoon beer and snack under a canopy of trees in the middle of town. At night, check in at the buzzy new Manchester Hotel, and then walk over to Lexington’s Distillery District to catch a show at live music venue The Burl. Before you leave, make sure to take a drive outside the city at some point — the horse farms (and fall foliage) surrounding it can’t be beat.


Image from Bob Krist/The Image Bank/Getty Images

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