Kentucky road trips and scenic drives

7 back-roads routes touch Kentucky, with 50 curated stops along them and 4 ready-made itineraries crossing the state.

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Routes through Kentucky

The Trail of Tears: Georgia to Kentucky
the northern road of the removal
New Echota → Hopkinsville · ~350 mi · 3 days · skips I-75 / I-24
The Wilderness Road
Boone's gap and the first West
Bristol → Berea · ~220 mi · 2–3 days · skips I-75 / I-81
US 60: The Mutton Line
Louisville to Paducah the long way
Louisville → Paducah · ~220 mi · 2 days · skips I-64 / the parkways
Bourbon, Bluegrass & Shakers
US 68 and the old Kentucky pikes
Lexington → Mammoth Cave · ~180 mi · 2–3 days · skips I-64 / I-65
US 127: The Plateau & the Sale
Sequatchie to York country
Chattanooga → Albany, KY · ~160 mi · 2 days · skips I-40
Moonbows & the Gorge
Red River Gorge to Cumberland Falls
Slade → Cumberland Falls · ~150 mi · 2 days · skips I-75 (mostly)
US 23: The Country Music Highway
coal seams and gold records
Ashland → Pikeville · ~140 mi · 1–2 days · skips I-64

Ready-made itineraries that cross Kentucky

Other states: Alabama · Arkansas · Florida · Georgia · Louisiana · Mississippi · North Carolina · South Carolina · Tennessee · Texas · Virginia · West Virginia.

Frequently asked questions

How many Kentucky road trips are there, and how long do they take?

7 routes cross Kentucky, from 1 day to 3 days each; driven back to back they add up to about 1,420 miles.

What is the longest drive in Kentucky?

The Trail of Tears: Georgia to Kentucky at about 350 miles (New Echota → Hopkinsville), a 3-day drive.

What is the best weekend drive in Kentucky?

US 23: The Country Music Highway: about 140 miles, 1–2 days, Ashland → Pikeville.

Which neighboring states do Kentucky routes continue into?

These routes carry on into Tennessee, Georgia and Virginia.