How far is Ashland, KY from Middlesboro, KY?
The driving distance from Ashland, KY to Middlesboro, KY is about 191.1 miles (307.5 km), with a travel time of about 04h 05m by car.
- The straight-line flight distance is about 142 miles (228.6 km).
- For a round trip, plan for roughly 08h 11m 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 05m.
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.
Mostly Sunny then Slight Chance Rain Showers
Driving Route Map
The map below follows the saved road route between Ashland and Middlesboro.
Turn-by-Turn Driving Directions
Step-by-step road directions between Ashland and Middlesboro.
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1
Start on 17th Street
70 m · 14 sec · 17th Street
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2
Turn right onto Greenup Avenue
3.4 mi · 4 min · Greenup Avenue
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3
Continue on Center Street
1.3 km · 56 sec · Center Street
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4
Continue on Walnut Street
1.2 mi · 1 min · Walnut Street
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5
Continue on Louisa Street
1.1 mi · 1 min · Louisa Street
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6
Continue on Louisa Road
57.1 mi · 1 hr 5 min · Louisa Road
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7
Continue straight
9.6 mi · 11 min
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8
Take the exit slight right
674 ft · 19 sec
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9
Keep slight left
99 m · 12 sec
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10
Turn right
42.3 mi · 48 min
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11
Continue on Hal Rogers Parkway
15 mi · 17 min · Hal Rogers Parkway
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12
Turn left
3.5 mi · 5 min
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13
At the end of the road, turn left onto Main Street
1.2 mi · 2 min · Main Street
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14
Continue on Harlan Road
10.7 mi · 16 min · Harlan Road
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15
Turn right onto Middle Fork Road
10.7 mi · 19 min · Middle Fork Road
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16
Continue on Middle Fork Road
5.7 mi · 10 min · Middle Fork Road
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17
Turn sharp right onto Straight Creek Road
1.8 mi · 3 min · Straight Creek Road
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18
Continue on Stoney Fork Road
12.6 mi · 22 min · Stoney Fork Road
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19
At the end of the road, turn left onto State Highway 66
1.6 km · 2 min · State Highway 66
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20
Continue on Jones Avenue
3054 ft · 1 min · Jones Avenue
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21
Turn left onto Bob Madon Bypass
4.6 mi · 5 min · Bob Madon Bypass
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22
Continue on Wilderness Road
5.2 mi · 6 min · Wilderness Road
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23
Continue on Pineville Road
1.6 km · 1 min · Pineville Road
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24
Continue on 12th Street
1.6 km · 1 min · 12th Street
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25
Turn right onto East Cumberland Avenue
1.3 km · 2 min · East Cumberland Avenue
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26
Turn right onto 21st Street
155 m · 28 sec · 21st Street
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27
Turn left onto Lothbury Avenue
53 m · 8 sec · Lothbury Avenue
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28
Arrive at your destination
0 m · 1 sec · Lothbury Avenue
Car Route Details
A richer read on the saved driving route between Ashland 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.
Louisa Road
Continue on Louisa Road
57.1 mi · 01h 05m
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.
Rain Showers leaving Ashland and Mostly Sunny then Slight Chance Rain Showers near Middlesboro.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Ashland to Middlesboro?
The road trip is about 191.1 miles (307.5 km) and usually takes 04h 05m 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 94.9 miles from Ashland and 96.2 miles from Middlesboro.
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 49.1 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 $26.93 one way or $53.85 round trip. Estimated CO2 is about 59.9 kg one way.
What should you check before leaving?
Before you leave, expect Rain Showers around Ashland and Mostly Sunny then Slight Chance Rain Showers near Middlesboro.
Flight Path Map
This map shows the direct air route between Ashland and Middlesboro. Straight-line distance: 142.07 mi (228.64 km).
#1 Ashland
City in Boyd County, Kentucky, United States
| Population | 20,070 |
| Coordinates | 38.4784100, -82.6379400 |
| Altitude | 168 |
| 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: 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 | $26.93 | $53.85 |
| Mid-grade | $4.56 | $30.73 | $61.47 |
| Premium | $5.00 | $33.69 | $67.37 |
| Diesel | $6.12 | $41.23 | $82.46 |
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