How far is Ironville, KY from Middlesboro, KY?
The driving distance from Ironville, KY to Middlesboro, KY is about 195.7 miles (314.9 km), with a travel time of about 04h 15m by car.
- The straight-line flight distance is about 139.5 miles (224.5 km).
- For a round trip, plan for roughly 08h 30m 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 15m.
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.
City in Kentucky, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Sunny
Driving Route Map
The map below follows the saved road route between Ironville and Middlesboro.
Turn-by-Turn Driving Directions
Step-by-step road directions between Ironville and Middlesboro.
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1
Start on Tiffany Drive
116 m · 17 sec · Tiffany Drive
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2
Continue on Brett Street
160 m · 28 sec · Brett Street
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3
At the end of the road, turn left onto Pine Street
48 m · 8 sec · Pine Street
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4
Turn left onto West Donta Road
3126 ft · 1 min · West Donta Road
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5
Turn straight onto Roberts Drive
2819 ft · 1 min · Roberts Drive
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6
Turn right onto Winslow Road
1666 ft · 48 sec · Winslow Road
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7
At the end of the road, turn left onto 13th Street
2.6 mi · 4 min · 13th Street
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8
Turn right onto Winchester Avenue
109 m · 7 sec · Winchester Avenue
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9
Enter the roundabout and take exit 3 toward 14th Street
31 m · 2 sec · 14th Street
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10
Exit the roundabout onto 14th Street
114 m · 18 sec · 14th Street
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11
At the end of the road, turn right onto Greenup Avenue
3.6 mi · 4 min · Greenup Avenue
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12
Continue on Center Street
1.3 km · 56 sec · Center Street
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13
Continue on Walnut Street
1.2 mi · 1 min · Walnut Street
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14
Continue on Louisa Street
1.1 mi · 1 min · Louisa Street
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15
Continue on Louisa Road
57.1 mi · 1 hr 5 min · Louisa Road
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16
Continue straight
9.6 mi · 11 min
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17
Take the exit slight right
674 ft · 19 sec
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18
Keep slight left
99 m · 12 sec
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19
Turn right
42.3 mi · 48 min
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20
Continue on Hal Rogers Parkway
15 mi · 17 min · Hal Rogers Parkway
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21
Turn left
3.5 mi · 5 min
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22
At the end of the road, turn left onto Main Street
1.2 mi · 2 min · Main Street
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23
Continue on Harlan Road
10.7 mi · 16 min · Harlan Road
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24
Turn right onto Middle Fork Road
10.7 mi · 19 min · Middle Fork Road
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25
Continue on Middle Fork Road
5.7 mi · 10 min · Middle Fork Road
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26
Turn sharp right onto Straight Creek Road
1.8 mi · 3 min · Straight Creek Road
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27
Continue on Stoney Fork Road
12.6 mi · 22 min · Stoney Fork Road
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28
At the end of the road, turn left onto State Highway 66
1.6 km · 2 min · State Highway 66
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29
Continue on Jones Avenue
3054 ft · 1 min · Jones Avenue
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30
Turn left onto Bob Madon Bypass
4.6 mi · 5 min · Bob Madon Bypass
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31
Continue on Wilderness Road
5.2 mi · 6 min · Wilderness Road
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32
Continue on Pineville Road
1.6 km · 1 min · Pineville Road
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33
Continue on 12th Street
1.6 km · 1 min · 12th Street
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34
Turn right onto East Cumberland Avenue
1.3 km · 2 min · East Cumberland Avenue
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35
Turn right onto 21st Street
155 m · 28 sec · 21st Street
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36
Turn left onto Lothbury Avenue
53 m · 8 sec · Lothbury Avenue
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37
Arrive at your destination
0 m · 1 sec · Lothbury Avenue
Car Route Details
A richer read on the saved driving route between Ironville 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.
Sunny leaving Ironville and Sunny near Middlesboro.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Ironville to Middlesboro?
The road trip is about 195.7 miles (314.9 km) and usually takes 04h 15m 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?
Wayland is a useful midpoint, sitting about 97.9 miles from Ironville and 97.8 miles from Middlesboro.
How much longer is the road route than the straight-line distance?
The direct path is about 139.5 miles (224.5 km), while the road route adds roughly 56.2 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 8:30 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $26.02 one way or $52.04 round trip. Estimated CO2 is about 61.3 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Ironville and Sunny near Middlesboro.
Stop Ideas Near Wayland
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Wayland.
Huntington
Ashland Transportation Center
Flight Path Map
This map shows the direct air route between Ironville and Middlesboro. Straight-line distance: 139.47 mi (224.46 km).
#1 Ironville
A city located in Lawrence County, Kentucky.
| Population | 288,649 |
| Coordinates | 38.4564700, -82.6923800 |
| Altitude | 219 |
| 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: 315 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 06h 31m |
| 40 mph (64.37 km/h) | 04h 53m |
| 50 mph (80.47 km/h) | 03h 54m |
| 60 mph (96.56 km/h) | 03h 15m |
| 70 mph (112.65 km/h) | 02h 47m |
| 80 mph (129 km/h) | 02h 26m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $26.02 | $52.04 |
| Mid-grade | $4.25 | $29.35 | $58.69 |
| Premium | $4.65 | $32.11 | $64.23 |
| Diesel | $5.30 | $36.60 | $73.20 |
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 · Apr 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.