How far is Owensboro, KY from Middlesboro, KY?
The driving distance from Owensboro, KY to Middlesboro, KY is about 269.2 miles (433.3 km), with a travel time of about 05h 12m by car.
- The straight-line flight distance is about 203.6 miles (327.6 km).
- For a round trip, plan for roughly 10h 24m 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 12m.
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 Adair County, Kentucky, United States
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 Owensboro and Middlesboro.
Turn-by-Turn Driving Directions
Step-by-step road directions between Owensboro and Middlesboro.
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1
Start on Frederica Street
1.1 mi · 2 min · Frederica Street
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2
Turn left onto West 18th Street
2675 ft · 1 min · West 18th Street
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3
Turn right onto Triplett Street
1156 ft · 28 sec · Triplett Street
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4
Turn straight onto New Hartford Road
1.9 mi · 3 min · New Hartford Road
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5
Turn left
1700 ft · 43 sec
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6
Merge slight left onto Wendell Ford Expressway
2274 ft · 30 sec · Wendell Ford Expressway
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7
Take the exit slight right toward I 165 South: Bowling Green
2273 ft · 56 sec
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8
Continue straight
62.4 mi · 1 hr 7 min
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9
Take the exit slight right
826 ft · 20 sec
-
10
Turn left onto Morgantown Road
1.8 mi · 3 min · Morgantown Road
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11
Turn left onto Old Morgantown Road
1 mi · 3 min · Old Morgantown Road
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12
Turn left onto University Boulevard
110 m · 9 sec · University Boulevard
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13
Continue on Kentucky Street
1.6 mi · 3 min · Kentucky Street
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14
Continue on Louisville Road
2.8 mi · 4 min · Louisville Road
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15
Turn right
1.2 km · 1 min
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16
Keep slight left
1.1 km · 1 min
-
17
Merge slight left
14.5 mi · 15 min
-
18
Take the exit slight right toward Somerset, Glasgow
2467 ft · 1 min
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19
Merge slight left onto Cumberland Parkway
85.6 mi · 1 hr 32 min · Cumberland Parkway
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20
Take the exit slight right toward KY 914: Somerset, Burnside
1523 ft · 32 sec
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21
Continue straight
2045 ft · 34 sec
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22
Turn left
33.8 mi · 41 min
-
23
Take the exit right
1778 ft · 43 sec
-
24
Merge slight left
11.3 mi · 12 min
-
25
Take the exit slight right toward US 25, US 25E: Corbin, Barbourville
1752 ft · 38 sec
-
26
Turn left onto Corbin Bypass
2 mi · 3 min · Corbin Bypass
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27
Continue on Cumberland Gap Parkway
30.7 mi · 37 min · Cumberland Gap Parkway
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28
Continue on Bob Madon Bypass
5.3 mi · 7 min · Bob Madon Bypass
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29
Continue on Wilderness Road
5.2 mi · 6 min · Wilderness Road
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30
Continue on Pineville Road
1.6 km · 1 min · Pineville Road
-
31
Continue on 12th Street
1.6 km · 1 min · 12th Street
-
32
Turn right onto East Cumberland Avenue
1.3 km · 2 min · East Cumberland Avenue
-
33
Turn right onto 21st Street
155 m · 28 sec · 21st Street
-
34
Turn left onto Lothbury Avenue
53 m · 8 sec · Lothbury Avenue
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35
Arrive at your destination
0 m · 1 sec · Lothbury Avenue
Car Route Details
A richer read on the saved driving route between Owensboro 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 Owensboro and Sunny near Middlesboro.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Owensboro to Middlesboro?
The road trip is about 269.2 miles (433.3 km) and usually takes 05h 12m 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?
Columbia is a useful midpoint, sitting about 134.5 miles from Owensboro and 134.7 miles from Middlesboro.
How much longer is the road route than the straight-line distance?
The direct path is about 203.6 miles (327.6 km), while the road route adds roughly 65.6 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 6:36 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $35.82 one way or $71.65 round trip. Estimated CO2 is about 84.4 kg one way.
Do you cross a time zone on this route?
Yes. There is about a 1 hour time difference between Owensboro 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 Owensboro and Sunny near Middlesboro.
Flight Path Map
This map shows the direct air route between Owensboro and Middlesboro. Straight-line distance: 203.55 mi (327.59 km).
#1 Owensboro
The most populous city in Daviess County, Kentucky.
| Population | 60,344 |
| Coordinates | 37.7742200, -87.1133300 |
| Altitude | 120 |
| 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: 433 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 08h 58m |
| 40 mph (64.37 km/h) | 06h 43m |
| 50 mph (80.47 km/h) | 05h 23m |
| 60 mph (96.56 km/h) | 04h 29m |
| 70 mph (112.65 km/h) | 03h 50m |
| 80 mph (129 km/h) | 03h 21m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $35.82 | $71.65 |
| Mid-grade | $4.25 | $40.40 | $80.81 |
| Premium | $4.65 | $44.21 | $88.43 |
| Diesel | $5.30 | $50.39 | $100.78 |
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.