How far is Oregon, KY from Middlesboro, KY?
The driving distance from Oregon, KY to Middlesboro, KY is about 136.6 miles (219.9 km), with a travel time of about 02h 46m by car.
- The straight-line flight distance is about 108.7 miles (175 km).
- For a round trip, plan for roughly 05h 32m 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 46m.
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.
Chance Showers And Thunderstorms
Sunny
Driving Route Map
The map below follows the saved road route between Oregon and Middlesboro.
Turn-by-Turn Driving Directions
Step-by-step road directions between Oregon and Middlesboro.
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1
Start on Oregon Road
2.1 mi · 8 min · Oregon Road
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2
At the end of the road, turn left onto Louisville Road
8.4 mi · 10 min · Louisville Road
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3
Turn left
4.5 mi · 5 min
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4
At the end of the road, turn left onto Danville Road
2.5 mi · 3 min · Danville Road
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5
Continue on Harrodsburg Road
2.3 mi · 3 min · Harrodsburg Road
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6
Continue on North Danville Byp
2.1 mi · 2 min · North Danville Byp
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7
Continue on South Danville Bypass
5.5 mi · 7 min · South Danville Bypass
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8
Continue on Stanford Road
2 mi · 2 min · Stanford Road
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9
Continue on Danville Road
29 mi · 34 min · Danville Road
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10
Continue on South Daniel Boone Trail
2 mi · 3 min · South Daniel Boone Trail
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11
Take the ramp slight right
1159 ft · 28 sec
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12
Merge slight left
29.6 mi · 32 min
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13
Take the exit slight right toward US 25, US 25E: Corbin, Barbourville
1752 ft · 38 sec
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14
Turn left onto Corbin Bypass
2 mi · 3 min · Corbin Bypass
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15
Continue on Cumberland Gap Parkway
30.7 mi · 37 min · Cumberland Gap Parkway
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16
Continue on Bob Madon Bypass
5.3 mi · 7 min · Bob Madon Bypass
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17
Continue on Wilderness Road
5.2 mi · 6 min · Wilderness Road
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18
Continue on Pineville Road
1.6 km · 1 min · Pineville Road
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19
Continue on 12th Street
1.6 km · 1 min · 12th Street
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20
Turn right onto East Cumberland Avenue
1.3 km · 2 min · East Cumberland Avenue
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21
Turn right onto 21st Street
155 m · 28 sec · 21st Street
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22
Turn left onto Lothbury Avenue
53 m · 8 sec · Lothbury Avenue
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23
Arrive at your destination
0 m · 1 sec · Lothbury Avenue
Car Route Details
A richer read on the saved driving route between Oregon 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.
Cumberland Gap Parkway
Continue on Cumberland Gap Parkway
30.7 mi · 00h 37m
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.
Chance Showers And Thunderstorms leaving Oregon and Sunny near Middlesboro.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Oregon to Middlesboro?
The road trip is about 136.6 miles (219.9 km) and usually takes 02h 46m 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 68.3 miles from Oregon and 68.4 miles from Middlesboro.
How much longer is the road route than the straight-line distance?
The direct path is about 108.7 miles (175 km), while the road route adds roughly 27.9 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 12:58 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $19.26 one way or $38.51 round trip. Estimated CO2 is about 42.8 kg one way.
What should you check before leaving?
Before you leave, expect Chance Showers And Thunderstorms around Oregon and Sunny near Middlesboro.
Flight Path Map
This map shows the direct air route between Oregon and Middlesboro. Straight-line distance: 108.73 mi (174.98 km).
#1 Oregon
Oregon is a place in Kentucky, United States.
| Population | 0 |
| Coordinates | 37.9123000, -84.8235600 |
| Altitude | 159 |
| 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: 220 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 04h 33m |
| 40 mph (64.37 km/h) | 03h 24m |
| 50 mph (80.47 km/h) | 02h 43m |
| 60 mph (96.56 km/h) | 02h 16m |
| 70 mph (112.65 km/h) | 01h 57m |
| 80 mph (129 km/h) | 01h 42m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.00 | $19.26 | $38.51 |
| Mid-grade | $4.56 | $21.98 | $43.96 |
| Premium | $5.00 | $24.09 | $48.18 |
| Diesel | $6.12 | $29.48 | $58.97 |
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