How far is Lexington-Fayette, KY from Middlesboro, KY?
The driving distance from Lexington-Fayette, KY to Middlesboro, KY is about 129.7 miles (208.7 km), with a travel time of about 02h 29m by car.
- The straight-line flight distance is about 107.6 miles (173.2 km).
- For a round trip, plan for roughly 04h 58m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 02h 29m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
You are leaving earlier than the recommended window, which gives you extra margin for breaks and traffic.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
City in Kentucky, US
Route Weather Snapshot
Check the forecast at both ends before you head out.
Partly Sunny
Partly Sunny
Driving Route Map
The map below follows the saved road route between Lexington-Fayette and Middlesboro.
Turn-by-Turn Driving Directions
Step-by-step road directions between Lexington-Fayette and Middlesboro.
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1
Start on the route
560 ft · 43 sec
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2
At the end of the road, turn right onto Floyd Drive
937 ft · 26 sec · Floyd Drive
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3
Turn right onto East New Circle Road
2414 ft · 50 sec · East New Circle Road
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4
Take the exit slight right toward US 60: Winchester, Lexington
539 ft · 15 sec
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5
Keep slight left to continue on US 60 East: Winchester
663 ft · 20 sec
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6
Continue on Winchester Road
1.8 mi · 2 min · Winchester Road
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7
Take the exit right
1358 ft · 33 sec
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8
Merge slight left
80.3 mi · 1 hr 26 min
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9
Take the exit slight right toward US 25, US 25E: Corbin, Barbourville
1752 ft · 38 sec
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10
Turn left onto Corbin Bypass
2 mi · 3 min · Corbin Bypass
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11
Continue on Cumberland Gap Parkway
30.7 mi · 37 min · Cumberland Gap Parkway
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12
Continue on Bob Madon Bypass
5.3 mi · 7 min · Bob Madon Bypass
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13
Continue on Wilderness Road
5.2 mi · 6 min · Wilderness Road
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14
Continue on Pineville Road
1.6 km · 1 min · Pineville Road
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15
Continue on 12th Street
1.6 km · 1 min · 12th Street
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16
Turn right onto East Cumberland Avenue
1.3 km · 2 min · East Cumberland Avenue
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17
Turn right onto 21st Street
155 m · 28 sec · 21st Street
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18
Turn left onto Lothbury Avenue
53 m · 8 sec · Lothbury Avenue
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19
Arrive at your destination
0 m · 1 sec · Lothbury Avenue
Car Route Details
A richer read on the saved driving route between Lexington-Fayette and Middlesboro.
Straightforward drive
The saved road route has a manageable number of maneuvers and should be easy to follow with normal attention to signs.
Winchester Road
Merge slight left
80.3 mi · 01h 26m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Partly Sunny leaving Lexington-Fayette and Partly Sunny near Middlesboro.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Lexington-Fayette to Middlesboro?
The road trip is about 129.7 miles (208.7 km) and usually takes 02h 29m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Livingston is a useful midpoint, sitting about 64.9 miles from Lexington-Fayette and 64.8 miles from Middlesboro.
How much longer is the road route than the straight-line distance?
The direct path is about 107.6 miles (173.2 km), while the road route adds roughly 22.1 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 1:32 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $17.27 one way or $34.54 round trip. Estimated CO2 is about 40.7 kg one way.
What should you check before leaving?
Before you leave, expect Partly Sunny around Lexington-Fayette and Partly Sunny near Middlesboro.
Flight Path Map
This map shows the direct air route between Lexington-Fayette and Middlesboro. Straight-line distance: 107.61 mi (173.18 km).
#1 Lexington-Fayette
The most populous city in Kentucky and the center of the Lexington-Fayette metropolitan area.
| Population | 314,488 |
| Coordinates | 38.0498000, -84.4585500 |
| Altitude | 305 |
| Country | United States |
#2 Middlesboro
City in Bell County, Kentucky, United States of America
| Population | 10,730 |
| Coordinates | 36.6084200, -83.7165800 |
| Altitude | 348 |
| Country | United States |
End: Middlesboro (-83.71658, 36.60842)
Estimated Travel Time
Distance: 209 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 04h 19m |
| 40 mph (64.37 km/h) | 03h 14m |
| 50 mph (80.47 km/h) | 02h 35m |
| 60 mph (96.56 km/h) | 02h 09m |
| 70 mph (112.65 km/h) | 01h 51m |
| 80 mph (129 km/h) | 01h 37m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $17.27 | $34.54 |
| Mid-grade | $4.25 | $19.48 | $38.96 |
| Premium | $4.65 | $21.32 | $42.63 |
| Diesel | $5.30 | $24.29 | $48.58 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in Kentucky · May 30, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.