Roads Worth Driving in Kentucky

The best drives in Kentucky are Old Frankfort Pike and Paris Pike in horse country, the Nada Tunnel road into Red River Gorge, US 23 through the eastern mountains, and the Trace through Land Between the Lakes. None of them are fast, and that's the point.

Kentucky is a long state. It takes hours to cross it, and the interstate versions of those hours all look the same. Get off I-64 or I-75 almost anywhere and the state changes fast: stone fences, tobacco barns, dry creek beds, switchbacks, lake water. Here are the roads that reward the exit.

Old Frankfort Pike and Paris Pike: the horse country loop

Start with the obvious one, because it's obvious for a reason. Old Frankfort Pike runs between Lexington and Frankfort through the middle of thoroughbred country. It's narrow, shaded by trees that meet over the road in places, and lined with the dry-laid stone fences that people photograph and then fail to describe accurately. Horse farms sit on both sides, with the kind of fencing and barns that suggest the horses live better than most people.

Paris Pike, which runs from Lexington toward Paris, is the wider, faster cousin. When it was rebuilt, the road was designed around the landscape instead of through it, so it curves with the land and keeps the old trees. It's one of the few divided roads anywhere that feels like a country lane.

Do both as a loop on a spring or fall morning. Stop in Midway, a small town built around a rail line running down the middle of its main street, and get a coffee. This stretch of the state is what people picture when they picture Kentucky, and for once the picture is accurate. It's the same landscape that shows up on the Script Kentucky Tee, more or less: rolling green, black fences, nothing in a hurry.

KY 77 and the Nada Tunnel: the way into Red River Gorge

The Red River Gorge, east of Lexington in the Daniel Boone National Forest, is the state's best-known chunk of wild land: sandstone arches, cliff lines, climbers everywhere. The classic way in is KY 77 through the Nada Tunnel, a one-lane tunnel blasted through rock for a logging railroad. One lane means one lane. You wait your turn, flash your lights, and creep through a hole in the mountain that drips on your roof.

Once you're through, the roads inside the Gorge — KY 715 among them — wind along the river and under the cliffs. Drive them slowly with the windows down. Things worth knowing:

• Weekends in October are packed. Go on a weekday if you can, or go early.
• Cell service is unreliable in the Gorge. Download your maps before you lose signal at Slade.
• Miguel's Pizza near the Gorge entrance is the unofficial basecamp for climbers and worth a stop whether you climb or not.
• Pull-offs are small. If a trailhead lot is full, it's full; don't park on the shoulder of a blind curve.

US 23: the Country Music Highway

US 23 runs north to south through far eastern Kentucky, through the coalfield counties along the Big Sandy, and it's officially designated the Country Music Highway because of how many country singers came out of the towns along it. The signs along the road name them county by county.

This is mountain driving, but on a good four-lane, so you can look around. The hills close in, the towns — Paintsville, Prestonsburg, Pikeville — sit in the valleys, and the road follows the water because everything in eastern Kentucky follows the water. In Pikeville, the Pikeville Cut-Through is worth seeing: an enormous channel carved through a mountain to reroute the road, the river, and the railroad all at once. There's an overlook where you can take in the scale of it.

If you want the slower, older version of the same country, drop onto US 460 or KY 80 and take the two-lane roads through the hollows. That's where the real driving is, and where you'll want a full tank, because gas stations get sparse.

The Trace through Land Between the Lakes

At the other end of the state, between Kentucky Lake and Lake Barkley, sits Land Between the Lakes National Recreation Area — a long peninsula of forest with water on both sides. One main road runs down its spine, called the Trace, and it's the closest thing Kentucky has to a national-park drive.

It's flat-ish, quiet, and green, with side roads dropping down to boat ramps and campgrounds. The Elk and Bison Prairie, a drive-through enclosure partway down, lets you idle past bison from the driver's seat, which is not a sentence most people expect to apply to Kentucky. Watch for deer at dusk the whole length of the road. Western Kentucky in general is lake country — slower, hotter in summer, built around fishing and pontoon boats — and it feels like a different state from the Bluegrass. It is a different state, culturally. Kentuckians will tell you this themselves.

The bourbon back roads around Bardstown

You can hit the big distilleries from the interstate. Don't. The roads between them are the better part of the trip. The two-lanes around Bardstown, Loretto, and Lawrenceburg run past black-stained warehouses sitting alone in fields — the dark color comes from a fungus that grows where whiskey ages, and once you notice it you'll see it everywhere.

KY 49 and KY 52 down toward Maker's Mark in Loretto are narrow, hilly, and pretty. Bardstown itself has a courthouse-square downtown worth an hour on foot. A few practical notes:

• Distillery tours book up on fall weekends. Reserve ahead or plan to just drive and look.
• Someone has to drive. Kentucky's tasting pours are small, but they add up across three distilleries.
• The roads are shared with farm equipment and the occasional distillery truck. Pass with patience or not at all.

If you're building a Kentucky trip around any of these drives, the Kentucky collection has the shirts we make about the state — including the Kentucky Icons Tee, which covers most of what's in this post in one design.

How to drive Kentucky without ruining it

A few habits that make all of these roads better:

• Pull over for locals. On a two-lane, the pickup behind you is commuting, not sightseeing. Use the pull-offs.
• Fill up in towns. Rural Kentucky gas stations keep their own hours, and some of these stretches run long between them.
• Go in April-May or October. Summer haze flattens the views; those two windows give you redbuds and dogwoods or full fall color.
• Watch for horses, deer, and slow farm traffic. All three are routine, not exceptions.
• Eat where the parking lot is full at 11:30 a.m. This rule has never failed anyone in Kentucky.

Common questions

What is the most scenic drive in Kentucky?

Old Frankfort Pike between Lexington and Frankfort is the consensus pick: stone fences, horse farms, and tree canopy over a narrow road. For wilder scenery, the roads through Red River Gorge via the Nada Tunnel are the stronger choice.

When is the best time of year for a Kentucky road trip?

Mid-April through May and the month of October. Spring gets you redbuds and green pastures in horse country, and October gets you fall color in the Gorge and eastern mountains — though Gorge weekends in October are crowded.

Can you drive through the Nada Tunnel in a regular car?

Yes, standard cars and pickups fit fine, though it's a single lane and you take turns with oncoming traffic. Tall RVs and trailers should check clearance and consider another route into the Gorge.