How far is Middlesboro, KY from Oregon, KY?
The driving distance from Middlesboro, KY to Oregon, KY is about 136.5 miles (219.6 km), with a travel time of about 02h 30m by car.
- The straight-line flight distance is about 108.7 miles (175 km).
- For a round trip, plan for roughly 05h 01m 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 30m.
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.
Sunny
Chance Showers And Thunderstorms
Driving Route Map
The map below follows the saved road route between Middlesboro and Oregon.
Turn-by-Turn Driving Directions
Step-by-step road directions between Middlesboro and Oregon.
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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
Continue on Stanford Road
2.6 mi · 4 min · Stanford Road
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17
Continue on Wilderness Road
131 m · 15 sec · Wilderness Road
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18
Turn left onto West Main Street
1.4 km · 1 min · West Main Street
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19
Turn right onto North Maple Avenue
1 mi · 2 min · North Maple Avenue
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20
Continue on Harrodsburg Road
1.1 mi · 2 min · Harrodsburg Road
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21
Continue on Harrodsburg Road
2.3 mi · 3 min · Harrodsburg Road
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22
Continue on Danville Road
2.4 mi · 3 min · Danville Road
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23
Take the exit slight right
4.5 mi · 5 min
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24
Turn right onto Louisville Road
8.4 mi · 10 min · Louisville Road
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25
Turn right
55 m · 8 sec
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26
Continue on Oregon Road
2.1 mi · 8 min · Oregon Road
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27
Arrive at your destination
0 m · 1 sec · Oregon Road
Car Route Details
A richer read on the saved driving route between Middlesboro and Oregon.
Straightforward drive
The saved road route has a manageable number of maneuvers and should be easy to follow with normal attention to signs.
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 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.
Sunny leaving Middlesboro and Chance Showers And Thunderstorms near Oregon.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Middlesboro to Oregon?
The road trip is about 136.5 miles (219.6 km) and usually takes 02h 30m 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 67.2 miles from Middlesboro and 69.2 miles from Oregon.
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 27.8 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 1:28 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $19.22 one way or $38.43 round trip. Estimated CO2 is about 42.7 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Middlesboro and Chance Showers And Thunderstorms near Oregon.
Flight Path Map
This map shows the direct air route between Middlesboro and Oregon. Straight-line distance: 108.73 mi (174.98 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 Oregon
Oregon is a place in Kentucky, United States.
| Population | 0 |
| Coordinates | 37.9123000, -84.8235600 |
| Altitude | 159 |
| Country | United States |
End: Oregon Road (-84.823402, 37.912265)
Estimated Travel Time
Distance: 220 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 04h 32m |
| 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 56m |
| 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 | $19.22 | $38.43 |
| Mid-grade | $4.56 | $21.93 | $43.87 |
| Premium | $5.00 | $24.04 | $48.08 |
| Diesel | $6.12 | $29.42 | $58.85 |
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