How far is Henderson, KY from Middlesboro, KY?
The driving distance from Henderson, KY to Middlesboro, KY is about 297.8 miles (479.3 km), with a travel time of about 05h 42m by car.
- The straight-line flight distance is about 229.3 miles (369.1 km).
- For a round trip, plan for roughly 11h 25m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 AM CDT.
Reverse, save, or send this route
This drive is better planned with a longer stop or an overnight stay. Copy the route link, send it to another device, or print a clean version before you head out.
This drive is better planned with a longer stop or an overnight stay.
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 05h 42m.
An early departure helps you fit a real stop into the day without turning the return into a late-night drive.
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, U.
Route Weather Snapshot
Check the forecast at both ends before you head out.
Sunny
Driving Route Map
The map below follows the saved road route between Henderson and Middlesboro.
Turn-by-Turn Driving Directions
Step-by-step road directions between Henderson and Middlesboro.
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1
Start on the route
30 m · 9 sec
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2
Turn right onto Washington Street
65 m · 10 sec · Washington Street
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3
Turn right onto South Green Street
1360 ft · 39 sec · South Green Street
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4
Turn right onto 2nd Street
1.2 mi · 2 min · 2nd Street
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5
Keep slight left to continue on 2nd Street
534 ft · 10 sec · 2nd Street
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6
Take the ramp slight right
1194 ft · 29 sec
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7
Merge slight right
1.3 km · 53 sec
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8
Take the exit slight right toward Owensboro
1 km · 1 min
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9
Continue straight
23.2 mi · 25 min
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10
Take the exit slight right toward US 60 East: Hawesville
2027 ft · 34 sec
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11
Merge slight left onto Wendell Ford Expressway
6.2 mi · 7 min · Wendell Ford Expressway
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12
Take the exit slight right toward I 165 South: Bowling Green
2273 ft · 56 sec
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13
Continue straight
62.4 mi · 1 hr 7 min
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14
Take the exit slight right
826 ft · 20 sec
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15
Turn left onto Morgantown Road
1.8 mi · 3 min · Morgantown Road
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16
Turn left onto Old Morgantown Road
1 mi · 3 min · Old Morgantown Road
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17
Turn left onto University Boulevard
110 m · 9 sec · University Boulevard
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18
Continue on Kentucky Street
1.6 mi · 3 min · Kentucky Street
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19
Continue on Louisville Road
2.8 mi · 4 min · Louisville Road
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20
Turn right
1.2 km · 1 min
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21
Keep slight left
1.1 km · 1 min
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22
Merge slight left
14.5 mi · 15 min
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23
Take the exit slight right toward Somerset, Glasgow
2467 ft · 1 min
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24
Merge slight left onto Cumberland Parkway
85.6 mi · 1 hr 32 min · Cumberland Parkway
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25
Take the exit slight right toward KY 914: Somerset, Burnside
1523 ft · 32 sec
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26
Continue straight
2045 ft · 34 sec
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27
Turn left
33.8 mi · 41 min
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28
Take the exit right
1778 ft · 43 sec
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29
Merge slight left
11.3 mi · 12 min
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30
Take the exit slight right toward US 25, US 25E: Corbin, Barbourville
1752 ft · 38 sec
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31
Turn left onto Corbin Bypass
2 mi · 3 min · Corbin Bypass
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32
Continue on Cumberland Gap Parkway
30.7 mi · 37 min · Cumberland Gap Parkway
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33
Continue on Bob Madon Bypass
5.3 mi · 7 min · Bob Madon Bypass
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34
Continue on Wilderness Road
5.2 mi · 6 min · Wilderness Road
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35
Continue on Pineville Road
1.6 km · 1 min · Pineville Road
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36
Continue on 12th Street
1.6 km · 1 min · 12th Street
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37
Turn right onto East Cumberland Avenue
1.3 km · 2 min · East Cumberland Avenue
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38
Turn right onto 21st Street
155 m · 28 sec · 21st Street
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39
Turn left onto Lothbury Avenue
53 m · 8 sec · Lothbury Avenue
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40
Arrive at your destination
0 m · 1 sec · Lothbury Avenue
Car Route Details
A richer read on the saved driving route between Henderson and Middlesboro.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Cumberland Parkway
Merge slight left onto Cumberland Parkway
85.6 mi · 01h 32m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A longer out-and-back drive
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
Sunny leaving Henderson and Sunny near Middlesboro.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Henderson to Middlesboro?
The road trip is about 297.8 miles (479.3 km) and usually takes 05h 42m in normal driving conditions.
Is this a same-day trip or an overnight route?
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
What is the halfway point on this route?
Edmonton is a useful midpoint, sitting about 148.8 miles from Henderson and 149.1 miles from Middlesboro.
How much longer is the road route than the straight-line distance?
The direct path is about 229.3 miles (369.1 km), while the road route adds roughly 68.5 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 6:00 AM to 8:00 AM CDT. If you want a more comfortable same-day return, try to leave by 5:34 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $39.63 one way or $79.27 round trip. Estimated CO2 is about 93.4 kg one way.
Do you cross a time zone on this route?
Yes. There is about a 1 hour time difference between Henderson and Middlesboro, so arrival and return times should be read in local time.
What should you check before leaving?
Before you leave, expect Sunny around Henderson and Sunny near Middlesboro.
Flight Path Map
This map shows the direct air route between Henderson and Middlesboro. Straight-line distance: 229.35 mi (369.1 km).
#1 Henderson
City in and county seat of Henderson County, Kentucky, United States
| Population | 27,974 |
| Coordinates | 37.8361500, -87.5900100 |
| Altitude | 124 |
| 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: 479 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 09h 55m |
| 40 mph (64.37 km/h) | 07h 26m |
| 50 mph (80.47 km/h) | 05h 57m |
| 60 mph (96.56 km/h) | 04h 57m |
| 70 mph (112.65 km/h) | 04h 15m |
| 80 mph (129 km/h) | 03h 42m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $39.63 | $79.27 |
| Mid-grade | $4.25 | $44.70 | $89.40 |
| Premium | $4.65 | $48.91 | $97.83 |
| Diesel | $5.30 | $55.75 | $111.49 |
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 · Apr 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.