How far is Middlesboro, KY from Ashland, KY?
The driving distance from Middlesboro, KY to Ashland, KY is about 191.2 miles (307.7 km), with a travel time of about 04h 06m by car.
- The straight-line flight distance is about 142 miles (228.6 km).
- For a round trip, plan for roughly 08h 12m 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 06m.
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.
Human settlement in Knott County, Kentucky, United States of America
Route Weather Snapshot
Check the forecast at both ends before you head out.
Sunny
Rain Showers
Driving Route Map
The map below follows the saved road route between Middlesboro and Ashland.
Turn-by-Turn Driving Directions
Step-by-step road directions between Middlesboro and Ashland.
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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
9.8 mi · 11 min · Wilderness Road
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7
Turn right onto Pine Street
3054 ft · 1 min · Pine Street
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8
Continue on State Highway 66
1.5 km · 2 min · State Highway 66
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9
Turn right onto Stoney Fork Road
12.6 mi · 22 min · Stoney Fork Road
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10
Continue on Straight Creek Road
1.8 mi · 3 min · Straight Creek Road
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11
Turn sharp left
5.7 mi · 10 min
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12
At the end of the road, turn left onto Middle Fork Road
4.9 mi · 9 min · Middle Fork Road
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13
Continue on Middle Fork Road
5.8 mi · 10 min · Middle Fork Road
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14
At the end of the road, turn left onto Harlan Road
10.7 mi · 16 min · Harlan Road
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15
Continue on Main Street
1.2 mi · 2 min · Main Street
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16
Turn right
3.5 mi · 5 min
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17
At the end of the road, turn right onto Hal Rogers Parkway
15.1 mi · 17 min · Hal Rogers Parkway
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18
Continue straight
42.2 mi · 48 min
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19
Merge slight left onto Water Gap Road
101 m · 12 sec · Water Gap Road
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20
Take the exit left
1084 ft · 30 sec
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21
Merge slight left
67.8 mi · 1 hr 18 min
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22
Continue on Walnut Street
1.2 mi · 1 min · Walnut Street
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23
Continue on Center Street
1.3 km · 58 sec · Center Street
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24
Continue on Winchester Avenue
3.4 mi · 4 min · Winchester Avenue
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25
Turn left onto 17th Street
70 m · 10 sec · 17th Street
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26
Arrive at your destination
0 m · 1 sec · 17th Street
Car Route Details
A richer read on the saved driving route between Middlesboro and Ashland.
Straightforward drive
The saved road route has a manageable number of maneuvers and should be easy to follow with normal attention to signs.
Water Gap Road
Merge slight left
67.8 mi · 01h 18m
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 Rain Showers near Ashland.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Middlesboro to Ashland?
The road trip is about 191.2 miles (307.7 km) and usually takes 04h 06m 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?
Hindman is a useful midpoint, sitting about 95 miles from Middlesboro and 96.2 miles from Ashland.
How much longer is the road route than the straight-line distance?
The direct path is about 142 miles (228.6 km), while the road route adds roughly 49.2 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 8:48 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $26.97 one way or $53.93 round trip. Estimated CO2 is about 60 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Middlesboro and Rain Showers near Ashland.
Flight Path Map
This map shows the direct air route between Middlesboro and Ashland. Straight-line distance: 142.07 mi (228.64 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 Ashland
City in Boyd County, Kentucky, United States
| Population | 20,070 |
| Coordinates | 38.4784100, -82.6379400 |
| Altitude | 168 |
| Country | United States |
End: Ashland (-82.63794, 38.47841)
Estimated Travel Time
Distance: 308 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 06h 22m |
| 40 mph (64.37 km/h) | 04h 46m |
| 50 mph (80.47 km/h) | 03h 49m |
| 60 mph (96.56 km/h) | 03h 11m |
| 70 mph (112.65 km/h) | 02h 43m |
| 80 mph (129 km/h) | 02h 23m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.00 | $26.97 | $53.93 |
| Mid-grade | $4.56 | $30.78 | $61.56 |
| Premium | $5.00 | $33.74 | $67.47 |
| Diesel | $6.12 | $41.29 | $82.58 |
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