Small Towns in Kentucky Worth the Detour

If you only have time for a handful of Kentucky small towns, make them Midway, Bardstown, Berea, Maysville, Winchester, and Horse Cave. Each one sits close enough to a major road to justify the turn signal, and each one gives you something the exit ramp can't: bourbon aging in the next block, a train running down the middle of Main Street, or a cave entrance a few steps from the barber shop.

Kentucky rewards people who get off the interstate. The state is stitched together with two-lane roads like US 68 and US 60 that pass horse farms, tobacco barns, and courthouse squares that still function as courthouse squares. Here's where to stop.

Midway: a train through the middle of everything

Midway is in Woodford County, a short detour off I-64 between Frankfort and Lexington, and its defining feature is right there in the layout: the railroad tracks run straight down the center of Main Street, with shops and restaurants facing each other across them. When a train comes through, everyone on both sidewalks stops and watches, because that's what you do.

The town is small enough to walk end to end in a few minutes, which is the point. Get a table at one of the restaurants along the tracks, then drive the surrounding roads. This is the heart of horse country, and the fences and barns out here are the picture people have in their heads when they think of the Bluegrass. Old Frankfort Pike, which runs nearby, is worth the drive on its own.

Bardstown: bourbon without the crowds

Bardstown calls itself the bourbon capital of the world, and it makes a decent case. Distilleries surround the town, several within a few minutes' drive, and downtown has the kind of intact historic core that most towns lost decades ago. My Old Kentucky Home State Park sits at the edge of town, tied to the Stephen Foster song the state adopted as its own.

The move here is to book one distillery tour, not four, and spend the rest of the day on foot. The courthouse square has bars and restaurants where bourbon is treated as a normal part of dinner rather than a themed experience. It's an easy detour off the Bluegrass Parkway, and it pairs well with a slow drive back toward Louisville on the smaller roads.

Berea: the craft town at the edge of the mountains

Berea sits right off I-75 south of Lexington, where the Bluegrass starts giving way to the foothills. It's known as Kentucky's folk arts and crafts town, and unlike a lot of places that claim an artsy identity, the work here is real. Berea College anchors the town, its students work in its shops and studios, and you can watch weaving, woodworking, and broom-making happening rather than just displayed.

Boone Tavern, the college's hotel and restaurant, is the traditional stop, and spoonbread is the traditional order. If you want to stretch your legs, the Pinnacles trails just outside town climb to rock outcrops with long views back over the ridge line. Berea is the rare detour that works equally well as a one-hour stop or a full weekend.

Maysville: the river town people forget

Maysville sits on the Ohio River in the state's northeast corner, along US 68, and it feels like a town that was once much bigger and decided to keep the good parts. The downtown runs parallel to the river, with a floodwall painted in murals telling the town's story. Rosemary Clooney grew up here, and the town has not forgotten it.

Order transparent pie while you're in town; it's a local specialty you won't find in many other places, a simple sugar-and-butter pie that sounds like nothing and isn't. Then walk the riverfront. The Ohio is wide and slow here, and watching barge traffic push past is a legitimate way to spend twenty minutes. If you're driving between Lexington and points northeast, US 68 through Maysville beats the interstate every time.

Winchester: Ale-8 and beer cheese

Winchester, just east of Lexington off I-64, gave Kentucky two things it takes seriously. The first is Ale-8-One, a ginger-citrus soft drink bottled in town and treated across central Kentucky as a birthright. The second is beer cheese, which Clark County claims as its own and celebrates accordingly. Both are worth trying at the source.

Winchester is also the practical gateway to the Red River Gorge. The Mountain Parkway starts nearby, and within an hour you're among the sandstone arches and cliff lines that make the Gorge one of the best places in the eastern United States to climb or hike. Stock the cooler in Winchester on the way in. Everyone does.

Horse Cave: the town with a cave under it

Horse Cave, off I-65 between Elizabethtown and Bowling Green, has a cave entrance in the middle of downtown. Hidden River Cave opens up steps from the storefronts, and you can walk down into it. The town's name is not a gimmick; the cave came first.

This stretch of Kentucky is karst country, riddled with sinkholes and underground rivers, and Mammoth Cave National Park is close by. Most people blow past on I-65 headed for Nashville. Horse Cave is the argument for stopping: a working small town sitting on top of a hole in the earth, matter-of-fact about it in a very Kentucky way.

Stringing them together

You can't do all six in a day, but you can build good loops:

• Bluegrass loop: Midway, Winchester, and Berea in a day from Lexington, mostly on two-lane roads.
• Bourbon and caves: Bardstown and Horse Cave work together on a north-south run along or near I-65.
• River run: Maysville anchors a US 68 drive through rolling farm country that's especially good in October.

Fall is the best season for all of it. Spring is a close second, when the horse farms are green and the redbuds are out along the highway cuts. We make apparel about these places because we drive these roads; the Script Kentucky Tee and the Kentucky Icons Tee both came out of trips like this, and the rest of our Kentucky designs live in the same collection. If you're the type who announces the state line out loud, the Welcome to Kentucky Tee exists for you.

Common questions

Which Kentucky small town is best for a first visit?

Berea, because it's directly off I-75 and works at any length of stop. You can eat, watch craftspeople work, and hike the Pinnacles without much planning. Midway is the pick if you'd rather see horse country.

Do I need to book distillery tours in Bardstown ahead of time?

For the well-known distilleries, yes, especially on weekends and during fall. Book one tour and leave the rest of the day open. Downtown Bardstown fills the remaining hours easily.

What's the best time of year for a Kentucky small-town road trip?

October, when the hills turn and the weather holds. April and May are the second choice, when the Bluegrass is at its greenest. Summer works but expect heat and humidity, particularly in the cave country along I-65.