Road trips from Lexington, KY

13 back-roads routes start within a 4.5-hour drive of Lexington, KY, including 0 day trips and 13 weekend drives; 2 ready-made itineraries begin nearby.

Drive times are estimates to the nearer end of each route (straight-line miles plus a quarter, at 50 mph); the atlas itself never routes you onto an interstate once the drive begins.

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Weekend road trips from Lexington, KY

Bourbon, Bluegrass & Shakers
Starts in Lexington
Lexington → Mammoth Cave · ~180 mi · 2–3 days · skips I-64 / I-65
The Wilderness Road
About 55 min to Berea
Bristol → Berea · ~220 mi · 2–3 days · skips I-75 / I-81
Moonbows & the Gorge
About 1 h 15 min to Slade
Slade → Cumberland Falls · ~150 mi · 2 days · skips I-75 (mostly)
US 60: The Mutton Line
About 1 h 45 min to Louisville
Louisville → Paducah · ~220 mi · 2 days · skips I-64 / the parkways
US 127: The Plateau & the Sale
About 2 h 30 min to Albany, KY
Chattanooga → Albany, KY · ~160 mi · 2 days · skips I-40
US 23: The Country Music Highway
About 2 h 40 min to Ashland
Ashland → Pikeville · ~140 mi · 1–2 days · skips I-64
US 52: The Mine Wars Road
About 3 h 5 min to Williamson
Bluefield → Williamson · ~100 mi · 1–2 days · skips I-77 (by a county)
US 11E: The Great Valley Road
About 3 h 40 min to Knoxville
Knoxville → Bristol · ~110 mi · 1–2 days · skips I-81 / I-26
The Midland Trail
About 3 h 55 min to Charleston
White Sulphur Springs → Charleston · ~120 mi · 1–2 days · skips I-64
The Crooked Road
About 4 h 5 min to Bristol
Bristol → Floyd · ~210 mi · 2–3 days · skips I-81
US 11: The Valley Road South
About 4 h 5 min to Bristol
Roanoke → Bristol · ~150 mi · 1–2 days · skips I-81
The Dragon & the Skyway
About 4 h 15 min to Loop from Gatlinburg
Loop from Gatlinburg · ~280 mi · 2–3 days · skips I-40 (by 200 miles)
The Overhill Country
About 4 h 15 min to Gatlinburg
Chattanooga → Gatlinburg · ~175 mi · 2 days · skips I-75

Longer itineraries starting near Lexington, KY

Other cities: Atlanta · Nashville · New Orleans · Houston · Dallas · Austin · San Antonio · Charlotte · Memphis · Birmingham · Charleston · Miami · Orlando · Tampa · Jacksonville · Louisville · Raleigh · Richmond · Knoxville · Chattanooga · Savannah · Little Rock · Baton Rouge · Mobile · Pensacola · Greenville, SC · Asheville · Virginia Beach · Columbia, SC · Washington, DC · Jackson, MS · Huntsville · Montgomery · Tallahassee · Myrtle Beach · Wilmington, NC · Oklahoma City.

Frequently asked questions

What is the closest route to Lexington, KY?

The nearest way in is Bourbon, Bluegrass & Shakers (Lexington → Mammoth Cave) — starts in Lexington; ~180 miles over 2–3 days.

What is a good day trip from Lexington, KY?

No one-day route starts within 2.5 hours of Lexington, KY; the nearest route overall is Bourbon, Bluegrass & Shakers (Lexington → Mammoth Cave) — starts in Lexington; ~180 miles over 2–3 days.

What is a good weekend road trip from Lexington, KY?

Bourbon, Bluegrass & Shakers (Lexington → Mammoth Cave) — starts in Lexington; ~180 miles over 2–3 days.

How far is the nearest parkway or scenic byway from Lexington, KY?

Natchez Trace Parkway begins about 4 h 30 min away at Nashville, beyond the 4.5-hour reach of a weekend start.