Trip from Oregon, KY to Middlesboro, KY

Compiled by the Trip.ovh editorial team · Last recalculated Apr 17, 2026 · Methodology

Drive Time

2h 46m

Distance

136.7 mi

220 km

Drive Score

9/10

Great drive

Same Day?

Yes, doable

Fuel Cost

$21

one way

EV Charging

Unknown

Best Time to Leave

Save up to 32 min

4 AM

2h 36m ★

6 AM

2h 46m

8 AM

3h 8m

10 AM

2h 54m

12 PM

2h 52m

3 PM

2h 55m

5 PM

3h 7m

8 PM

2h 40m

Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.

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Oregon, KY

Stephen Leonardi

Middlesboro, KY

Vietnam Hidden Light

Trip Overview

The drive from Oregon, KY to Middlesboro, KY covers 136.7 miles and takes about 2h 46m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.

The route leans on Danville Road, Cumberland Gap Parkway, I 75 for much of the mileage, and the overall profile is mixed drive. The longest uninterrupted segment is about 31.5 miles on Danville Road. At current regular gas prices, budget about $21.37 one way before food or hotel costs.

Trip Pace

Same-day drive is realistic

A same-day return is realistic if you keep stops short.

Break Rhythm

1 planned break

A short stop every 2 to 3 hours is enough for this drive.

Midpoint

68.3 miles from Oregon, KY

A natural place for your longest stop of the day , about 1h 25m into the drive .

Who Is This Route For?

Weekend Trip

Doable as a same-day drive at 2h 46m. Total distance: 136.7 miles.

Family Friendly

Moderate complexity with 1 natural rest stops along the way.

Solo Traveler

2h 46m drive, comfortable solo distance.

First-Time Driver

Mostly highway driving (47%). Straightforward navigation.

Scenic Drive

Mixed drive route profile with national parks nearby.

Drive Character

The drive from Oregon, KY to Middlesboro, KY covers 136.7 miles and takes about 2h 46m, using a mix of highways and local roads.

Expect a mix of faster highway mileage and slower local approaches near the beginning or end.

There are about 23 navigation steps in the underlying route data, so the final approach matters more than the middle miles.

Danville Road is the longest continuous segment at about 31.5 miles.

How Hard Is This Drive?

This route mixes highway mileage with some local-road sections near the start or finish. Navigation is very simple - set it and forget it for most of the drive. The trickiest moment comes around 90.2 miles in.

Driving Effort 2/10

Very easy - short and simple to drive

Balances navigation complexity with total wheel time.

The drive from Oregon, KY to Middlesboro, KY is easy. At 2h 46m with 47% highway, most drivers will find it relaxed and low-stress.

Where does it get tricky?

The main spots that need attention: at 90.2 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one; at 90.6 miles (US 25E / Corbin Bypass): Navigation decision point; at 135.7 miles (KY 74 / East Cumberland Avenue): Lane positioning matters here.

Critical Maneuvers

5 of 8 key points

These are the spots where you need to pay the most attention. Preview them before you drive.

90.2 mi into trip | ~1h 48m in

Take the exit toward US 25, US 25E: Corbin, Barbourville

Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one

Toward US 25, US 25E: Corbin, Barbourville

90.6 mi into trip | ~1h 49m in | US 25E / Corbin Bypass

Turn left onto US 25E / Corbin Bypass

Navigation decision point

135.7 mi into trip | ~2h 44m in | KY 74 / East Cumberland Avenue

Turn right onto KY 74 / East Cumberland Avenue

Lane positioning matters here

Use the right lane.

136.5 mi into trip | ~2h 45m in | 21st Street

Turn right onto 21st Street

Navigation decision point

136.6 mi into trip | ~2h 46m in | Lothbury Avenue

Turn left onto Lothbury Avenue

Navigation decision point

Towns Mentioned on Route Signs

Based on OSRM destination-sign hints, not a full list of every settlement the road passes.

On the drive from Oregon, KY to Middlesboro, KY, road signs begin pointing toward Barbourville along the way.

Barbourville

90.2 mi in | ~1h 48m

Main Roads

Road	Distance	Duration
Danville Road	31.5 mi	36m
Cumberland Gap Parkway	30.7 mi	36m
I 75	29.6 mi	31m
Louisville Road	8.4 mi	9m
South Danville Bypass	5.5 mi	6m
Bob Madon Bypass	5.3 mi	6m
Wilderness Road	5.2 mi	5m
US 127 Bypass	4.5 mi	5m

Longest stretch: Danville Road — 31.5 mi, about 36m

Turn-by-Turn Driving Directions

Step-by-step road directions between Oregon, KY and Middlesboro, KY.

Start on Oregon Road

2.1 mi · 8 min · Oregon Road

At end of road, turn left onto US 127

8.4 mi · 9 min · Louisville Road

Turn left onto US 127 Bypass

4.5 mi · 5 min · US 127 Bypass

At end of road, turn left onto US 127

2.5 mi · 2 min · Danville Road

Continue on US 127

2.3 mi · 2 min · Harrodsburg Road

Continue on US 127 Bypass

2.1 mi · 2 min · North Danville Byp

Continue on US 127 Bypass; US 150 Bypass

5.5 mi · 6 min · South Danville Bypass

Continue on US 150

2.0 mi · 2 min · Stanford Road

Continue on US 150

29 mi · 33 min · Danville Road

Continue on US 25

2.0 mi · 2 min · South Daniel Boone Trail

Take the ramp

0.2 mi · 28 sec

Merge onto I 75

30 mi · 31 min · I 75

Take the exit

0.3 mi · 37 sec

Toward US 25, US 25E: Corbin, Barbourville

Turn left onto US 25E

2.0 mi · 3 min · Corbin Bypass

Continue on US 25E

31 mi · 36 min · Cumberland Gap Parkway

Continue on US 25E

5.3 mi · 6 min · Bob Madon Bypass

Continue on US 25E

5.2 mi · 5 min · Wilderness Road

Continue on US 25E

1.0 mi · 1 min · Pineville Road

Continue on US 25E

1.0 mi · 1 min · 12th Street

Turn right onto KY 74

0.8 mi · 1 min · East Cumberland Avenue

Use the right lane.

Turn right onto 21st Street

509 ft · 28 sec · 21st Street

Turn left onto Lothbury Avenue

174 ft · 7 sec · Lothbury Avenue

Arrive at destination

Lothbury Avenue

Trip Plan

Morning Departure

Leave by 9 AM and you'll arrive before lunch.

Evening Departure

Even a 4 PM departure gets you there before dark in summer.

You can normally do this drive in one day.

Plan roughly 1 meaningful break for fuel, food, and rest.

The halfway point lands around 68.3 miles from Oregon, KY, or about 1h 25m into the drive.

The longest continuous stretch on this route runs about 31.5 miles.

This is a comfortable same-day trip.

Departure

Before you leave

Start with fuel, water, and navigation already sorted so the first hour feels easy.

First stop

Around 30 miles or 40m in

Use this first pause for coffee, a restroom break, and a quick traffic check ahead.

Halfway reset

Around 68.3 miles or 1h 25m in

This is the best place for your longest stop, a real meal, and a full fuel check.

Final approach

Final hour starts around 2h 15m

Traffic, exits, and arrival timing usually matter more near Middlesboro, KY than in the middle of the route.

Before You Leave

Open the route before leaving Oregon, KY so your first major turns are already loaded.

Leave with enough water and a charging cable within reach, not packed away.

Check your fuel range against the first long segment, especially if you are starting outside city service areas.

Day 1

Settle into the route from Oregon, KY

This is one driving day of about 136.7 miles and 2h 46m.

Your first comfortable stop window is around 30 miles from Oregon, KY.

This route can stay practical as a one-day drive if traffic stays reasonable.

Plan about 1 real break rather than only quick fuel stops.

The longest stretch is on Danville Road for about 31.5 miles.

Where to Stop

Rest stops, refuel points, and overnight suggestions along this route.

Halfway Point

Midpoint

About 68.3 mi from Oregon, KY · 1h 25m into the drive

city in Laurel County, Kentucky, United States

Mid-route town

Meal stop

London, KY

68 mi into the route

Best for: Lunch, fuel, and a longer reset

This sits close to the middle of the route, so it works well for the longest stop of the day.

Pacing Suggestions

Junction City, KY

Fuel and coffee

A short stop after about 30 miles helps settle the day before fatigue starts building.

London, KY

Meal break

The midpoint is around 68.3 miles from Oregon, KY, which is a good place for a longer meal and fuel stop.

Arriving in Middlesboro, KY

The final approach into Middlesboro, KY usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.

Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Middlesboro, KY.

These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.

National Parks Near This Route

Worth a detour if your schedule allows.

Cumberland Gap National Historical Park

National Historical Park

Cumberland Gap was the first great gateway to the west. Come follow the path of bison, Native Americans, longhunters, and pioneers. Walk where 300,000 people crossed the Appalachians to settle America...

5 mi from route ~14 min detour Free near mile 131.9

Park Closure: Little Yellow Creek Bridge Closure - Construction Underway

Park Closure: Bartlett Park Restrooms Closed

View on nps.gov

Camp Nelson National Monument

National Monument

The US Army established Camp Nelson as a fortified supply depot in April 1863. Over the next 3 years, the site evolved into a massive recruitment and training center for United States Colored Troops a...

13 mi from route ~33 min detour Free near mile 14.1

View on nps.gov

Mill Springs Battlefield National Monument

National Monument

The US won a significant victory early in the Civil War at the Battle of Mill Springs. Explore the rolling fields of Kentucky where the battle took place and learn about that state's strategic importa...

28 mi from route ~70 min detour Free near mile 56.5

View on nps.gov

Park data from the National Park Service API. Alerts update every 2 hours.

Fuel & Cost

Regular Gas

$21.37 one way

$42.74 round trip

$3.97/gal 25.4 MPG avg 48 kg CO₂

Fuel Type	$/gal	One Way	Round Trip
midgrade	$4.36	$23.47	$46.93
premium	$4.89	$26.31	$52.61
diesel	$5.61	$30.18	$60.36

No toll roads detected on this route.

Estimated Trip Cost (one way, 1 person)

Fuel

$21

Meals

$25–$50

Total

$46–$71

Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.

Estimated CO2 emission: 47.8 kg one way. Prices: EIA weekly data, 2026-04-13.

Driving Electric?

About $14 in charging · 0 stops · 67% less CO₂

Vehicle Type	kWh	DC Fast	Home Charge
Average EV	41	$14.35	$6.56
Efficient EV	34.2	$11.96	$5.47
EV Truck/SUV	54.7	$19.14	$8.75

Gas CO2

48 kg

EV CO2

16 kg (67% less)

This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.

DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.

Travel Intel

Current conditions at both ends of the drive.

Forecast as of Apr 15, 2026

Origin

Oregon, KY

Late night in Oregon on Friday

Local time

1:10 AM

EDT

Current temp

73°F

Unavailable

Live forecast

Destination

Middlesboro, KY

Late night in Middlesboro on Friday

Local time

1:10 AM

EDT

Current temp

72°F

Unavailable

Live forecast

48°F

London, KY

68 mi in

Seasonal Notes

Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.

Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.

Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.

Time zone

Same local time

Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.

Temperature spread

1 degrees cooler at arrival

A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.

Road read

2h 46m on the road

Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.

Weather data from the National Weather Service. Conditions may change; check closer to your travel date.

Frequently Asked Questions

The drive from Oregon, KY to Middlesboro, KY covers 136.7 miles and takes about 2h 46m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.

The main roads are Danville Road, Cumberland Gap Parkway, I 75. Expect a mix of highway and local road driving.

This is a comfortable same-day trip.

The midpoint is about 68.3 miles from Oregon, KY. Look for rest areas, gas stations, or food options near the halfway mark.

At current regular gas prices, expect to spend about $21.37 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.

Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.

Plan about 1 meaningful break for fuel, food, or rest. A short stop every 2 to 3 hours is enough for this drive.

The drive from Oregon, KY to Middlesboro, KY is easy. At 2h 46m with 47% highway, most drivers will find it relaxed and low-stress.

On the drive from Oregon, KY to Middlesboro, KY, road signs begin pointing toward Barbourville along the way.

Yes. Nearby national parks include Cumberland Gap National Historical Park, Camp Nelson National Monument and Mill Springs Battlefield National Monument.

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