How far is Middlesboro, KY from Oklahoma, KY?
The driving distance from Middlesboro, KY to Oklahoma, KY is about 251.9 miles (405.4 km), with a travel time of about 04h 31m by car.
- The straight-line flight distance is about 188.7 miles (303.7 km).
- For a round trip, plan for roughly 09h 02m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 AM EDT.
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 04h 31m.
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 Boyle County, Kentucky
Route Weather Snapshot
Check the forecast at both ends before you head out.
Sunny
Slight Chance Showers And Thunderstorms
Driving Route Map
The map below follows the saved road route between Middlesboro and Oklahoma.
Turn-by-Turn Driving Directions
Step-by-step road directions between Middlesboro and Oklahoma.
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1
Start on Lothbury Avenue
53 m · 10 sec · Lothbury Avenue
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2
Turn right onto 21st Street
155 m · 30 sec · 21st Street
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3
Turn left onto West Cumberland Avenue
1.3 km · 2 min · West Cumberland Avenue
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4
Turn left onto 12th Street
1.6 km · 1 min · 12th Street
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5
Continue on Pineville Road
1.6 km · 1 min · Pineville Road
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6
Continue on Wilderness Road
10.5 mi · 13 min · Wilderness Road
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7
Continue on Riverview Avenue
30.7 mi · 37 min · Riverview Avenue
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8
Continue on Corbin Bypass
1.9 mi · 3 min · Corbin Bypass
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9
Take the exit slight right toward I 75 North: Lexington
1811 ft · 24 sec
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10
Merge slight left
29.5 mi · 32 min
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11
Take the exit slight right toward US 25: Mount Vernon, Livingston
1303 ft · 32 sec
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12
Keep slight left
54 m · 6 sec
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13
Turn left onto South Daniel Boone Trail
2.1 mi · 3 min · South Daniel Boone Trail
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14
Continue on Crab Orchard Road
29 mi · 34 min · Crab Orchard Road
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15
Continue on Stanford Road
2 mi · 2 min · Stanford Road
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16
Turn straight onto South Danville Bypass
5.5 mi · 7 min · South Danville Bypass
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17
Turn left onto Perryville Road
7.7 mi · 9 min · Perryville Road
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18
Continue on East 2nd Street
1 mi · 1 min · East 2nd Street
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19
Continue on Springfield Road
15.6 mi · 18 min · Springfield Road
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20
Turn left
28 m · 1 sec
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21
Keep slight right
14.9 mi · 17 min
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22
Take the exit left toward Bluegrass Parkway West
1169 ft · 29 sec
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23
Merge slight left onto Bluegrass Parkway
23.9 mi · 26 min · Bluegrass Parkway
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24
Keep slight left
1.4 km · 2 min
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25
Merge slight left
1.2 mi · 1 min
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26
Take the exit slight right toward KY 61 South: Elizabethtown, Paducah, Western Kentucky Parkway
1079 ft · 26 sec
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27
Keep slight right to continue on US 31W: Elizabethtown, Paducah, Western Kentucky Parkway West
1286 ft · 32 sec
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28
Keep slight left to continue on Paducah, Elizabethtown
1710 ft · 42 sec
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29
Merge slight left onto Western Kentucky Parkway
29 mi · 31 min · Western Kentucky Parkway
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30
Take the exit slight right toward KY 259: Leitchfield, Brownsville
1619 ft · 41 sec
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31
Turn right onto South Main Street
1.5 km · 1 min · South Main Street
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32
Enter the roundabout and take exit 5 toward Public Square
101 m · 11 sec · Public Square
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33
Exit the roundabout onto Public Square
24 m · 2 sec · Public Square
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34
Turn slight right onto West Main Street
1.4 km · 2 min · West Main Street
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35
Continue on Owensboro Road
16.1 mi · 22 min · Owensboro Road
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36
Continue on Fordsville Road
13.3 mi · 23 min · Fordsville Road
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37
Continue straight
8.8 mi · 16 min
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38
Continue on Main Cross Street
1.5 mi · 3 min · Main Cross Street
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39
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Middlesboro and Oklahoma.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
Riverview Avenue
Continue on Riverview Avenue
30.7 mi · 00h 37m
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 Middlesboro and Slight Chance Showers And Thunderstorms near Oklahoma.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Middlesboro to Oklahoma?
The road trip is about 251.9 miles (405.4 km) and usually takes 04h 31m 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?
Perryville is a useful midpoint, sitting about 125.6 miles from Middlesboro and 126.3 miles from Oklahoma.
How much longer is the road route than the straight-line distance?
The direct path is about 188.7 miles (303.7 km), while the road route adds roughly 63.2 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 EDT. If you want a more comfortable same-day return, try to leave by 7:58 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $35.52 one way or $71.03 round trip. Estimated CO2 is about 79 kg one way.
Do you cross a time zone on this route?
Yes. There is about a 1 hour time difference between Middlesboro and Oklahoma, so arrival and return times should be read in local time.
What should you check before leaving?
Before you leave, expect Sunny around Middlesboro and Slight Chance Showers And Thunderstorms near Oklahoma.
Stop Ideas Near Perryville
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Perryville.
Louisville, Kentucky
Flight Path Map
This map shows the direct air route between Middlesboro and Oklahoma. Straight-line distance: 188.68 mi (303.65 km).
#1 Middlesboro
City in Bell County, Kentucky, United States of America
| Population | 10,730 |
| Coordinates | 36.6084200, -83.7165800 |
| Altitude | 348 |
| Country | United States |
#2 Oklahoma
Oklahoma is a place in Kentucky, United States.
| Population | 0 |
| Coordinates | 37.6617200, -86.8772100 |
| Altitude | 133 |
| Country | United States |
End: KY 764 (-86.877254, 37.66173)
Estimated Travel Time
Distance: 405 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 08h 23m |
| 40 mph (64.37 km/h) | 06h 17m |
| 50 mph (80.47 km/h) | 05h 02m |
| 60 mph (96.56 km/h) | 04h 11m |
| 70 mph (112.65 km/h) | 03h 35m |
| 80 mph (129 km/h) | 03h 08m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.00 | $35.52 | $71.03 |
| Mid-grade | $4.56 | $40.54 | $81.08 |
| Premium | $5.00 | $44.43 | $88.86 |
| Diesel | $6.12 | $54.38 | $108.76 |
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 · Oct 15, 2026