How far is Oklahoma, KY from Middlesboro, KY?
The driving distance from Oklahoma, KY to Middlesboro, KY is about 252.3 miles (406 km), with a travel time of about 05h 10m by car.
- The straight-line flight distance is about 188.7 miles (303.7 km).
- For a round trip, plan for roughly 10h 20m 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 10m.
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.
Slight Chance Showers And Thunderstorms
Sunny
Driving Route Map
The map below follows the saved road route between Oklahoma and Middlesboro.
Turn-by-Turn Driving Directions
Step-by-step road directions between Oklahoma and Middlesboro.
-
1
Start on the route
1.5 mi · 3 min
-
2
Turn right
39.1 mi · 1 hr 3 min
-
3
Enter the roundabout and take exit 1 toward Public Square
13 m · 1 sec · Public Square
-
4
Exit the roundabout onto Public Square
24 m · 1 sec · Public Square
-
5
Turn slight right onto South Main Street
1 mi · 2 min · South Main Street
-
6
Take the ramp left
820 ft · 20 sec
-
7
Merge slight left onto Western Kentucky Parkway
29.6 mi · 32 min · Western Kentucky Parkway
-
8
Take the exit slight right toward I 65 North: Lexington, Louisville
1955 ft · 48 sec
-
9
Keep slight left to continue on I 65 North: Lexington, Louisville
3052 ft · 1 min
-
10
Merge slight left
1.4 mi · 1 min
-
11
Take the exit slight right toward Lexington, Bardstown
3252 ft · 1 min
-
12
Continue on Bluegrass Parkway
23.8 mi · 26 min · Bluegrass Parkway
-
13
Take the exit slight right toward Bardstown
1394 ft · 34 sec
-
14
Turn right onto Springfield Road
5.6 mi · 6 min · Springfield Road
-
15
Continue on Bardstown Road
9.2 mi · 11 min · Bardstown Road
-
16
Keep slight left
28 m · 2 sec
-
17
Keep slight right
24.3 mi · 28 min
-
18
Turn right onto South Danville Bypass
5.5 mi · 7 min · South Danville Bypass
-
19
Continue on Stanford Road
2 mi · 2 min · Stanford Road
-
20
Continue on Danville Road
29 mi · 34 min · Danville Road
-
21
Continue on South Daniel Boone Trail
2 mi · 3 min · South Daniel Boone Trail
-
22
Take the ramp slight right
1159 ft · 28 sec
-
23
Merge slight left
29.6 mi · 32 min
-
24
Take the exit slight right toward US 25, US 25E: Corbin, Barbourville
1752 ft · 38 sec
-
25
Turn left onto Corbin Bypass
2 mi · 3 min · Corbin Bypass
-
26
Continue on Cumberland Gap Parkway
30.7 mi · 37 min · Cumberland Gap Parkway
-
27
Continue on Bob Madon Bypass
5.3 mi · 7 min · Bob Madon Bypass
-
28
Continue on Wilderness Road
5.2 mi · 6 min · Wilderness Road
-
29
Continue on Pineville Road
1.6 km · 1 min · Pineville Road
-
30
Continue on 12th Street
1.6 km · 1 min · 12th Street
-
31
Turn right onto East Cumberland Avenue
1.3 km · 2 min · East Cumberland Avenue
-
32
Turn right onto 21st Street
155 m · 28 sec · 21st Street
-
33
Turn left onto Lothbury Avenue
53 m · 8 sec · Lothbury Avenue
-
34
Arrive at your destination
0 m · 1 sec · Lothbury Avenue
Car Route Details
A richer read on the saved driving route between Oklahoma and Middlesboro.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
Longest stretch
Turn right
39.1 mi · 01h 03m
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.
Slight Chance Showers And Thunderstorms leaving Oklahoma and Sunny near Middlesboro.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Oklahoma to Middlesboro?
The road trip is about 252.3 miles (406 km) and usually takes 05h 10m 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 126.1 miles from Oklahoma and 126.3 miles from Middlesboro.
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 63.6 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 6:40 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $35.56 one way or $71.11 round trip. Estimated CO2 is about 79.1 kg one way.
Do you cross a time zone on this route?
Yes. There is about a 1 hour time difference between Oklahoma and Middlesboro, so arrival and return times should be read in local time.
What should you check before leaving?
Before you leave, expect Slight Chance Showers And Thunderstorms around Oklahoma and Sunny near Middlesboro.
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 Oklahoma and Middlesboro. Straight-line distance: 188.68 mi (303.65 km).
#1 Oklahoma
Oklahoma is a place in Kentucky, United States.
| Population | 0 |
| Coordinates | 37.6617200, -86.8772100 |
| Altitude | 133 |
| 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: 406 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 08h 24m |
| 40 mph (64.37 km/h) | 06h 18m |
| 50 mph (80.47 km/h) | 05h 02m |
| 60 mph (96.56 km/h) | 04h 12m |
| 70 mph (112.65 km/h) | 03h 36m |
| 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 | $35.56 | $71.11 |
| Mid-grade | $4.56 | $40.58 | $81.17 |
| Premium | $5.00 | $44.48 | $88.96 |
| Diesel | $6.12 | $54.44 | $108.88 |
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