How far is Valley Station, KY from Middlesboro, KY?
The driving distance from Valley Station, KY to Middlesboro, KY is about 201 miles (323.4 km), with a travel time of about 03h 56m by car.
- The straight-line flight distance is about 157.4 miles (253.3 km).
- For a round trip, plan for roughly 07h 53m 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 03h 56m.
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 Lincoln County, Kentucky
Route Weather Snapshot
Check the forecast at both ends before you head out.
Sunny
Sunny
Driving Route Map
The map below follows the saved road route between Valley Station and Middlesboro.
Turn-by-Turn Driving Directions
Step-by-step road directions between Valley Station and Middlesboro.
-
1
Start on Alanadale Drive
1492 ft · 1 min · Alanadale Drive
-
2
Turn right onto Dixie Highway
1.3 mi · 2 min · Dixie Highway
-
3
Take the exit slight right toward KY 841 East: Gene Snyder Freeway
1293 ft · 32 sec
-
4
Merge slight left onto Greenbelt Highway
94 m · 5 sec · Greenbelt Highway
-
5
Continue on Gene Snyder Freeway
16.9 mi · 20 min · Gene Snyder Freeway
-
6
Take the exit slight right toward US 31E, US 150: Louisville, Bardstown
2164 ft · 57 sec
-
7
Turn right onto Bardstown Road
4.8 mi · 6 min · Bardstown Road
-
8
Continue on Mt Washington Bypass
2.5 mi · 3 min · Mt Washington Bypass
-
9
Continue on Bardstown Rd;Louisville Road
2.6 mi · 3 min · Bardstown Rd;Louisville Road
-
10
Continue on Bardstown Road; Louisville Road
123 m · 5 sec · Bardstown Road; Louisville Road
-
11
Continue on Bardstown Rd; Louisville Road
1173 ft · 15 sec · Bardstown Rd; Louisville Road
-
12
Continue on Louisville Road
12.6 mi · 14 min · Louisville Road
-
13
Continue on North 3rd Street
1.3 mi · 2 min · North 3rd Street
-
14
Turn left onto East John Rowan Boulevard
3.3 mi · 4 min · East John Rowan Boulevard
-
15
At the end of the road, turn left onto Springfield Road
5.9 mi · 7 min · Springfield Road
-
16
Continue on Bardstown Road
9.2 mi · 11 min · Bardstown Road
-
17
Keep slight left
28 m · 2 sec
-
18
Keep slight right
24.3 mi · 28 min
-
19
Turn right onto South Danville Bypass
5.5 mi · 7 min · South Danville Bypass
-
20
Continue on Stanford Road
2 mi · 2 min · Stanford Road
-
21
Continue on Danville Road
29 mi · 34 min · Danville Road
-
22
Continue on South Daniel Boone Trail
2 mi · 3 min · South Daniel Boone Trail
-
23
Take the ramp slight right
1159 ft · 28 sec
-
24
Merge slight left
29.6 mi · 32 min
-
25
Take the exit slight right toward US 25, US 25E: Corbin, Barbourville
1752 ft · 38 sec
-
26
Turn left onto Corbin Bypass
2 mi · 3 min · Corbin Bypass
-
27
Continue on Cumberland Gap Parkway
30.7 mi · 37 min · Cumberland Gap Parkway
-
28
Continue on Bob Madon Bypass
5.3 mi · 7 min · Bob Madon Bypass
-
29
Continue on Wilderness Road
5.2 mi · 6 min · Wilderness Road
-
30
Continue on Pineville Road
1.6 km · 1 min · Pineville Road
-
31
Continue on 12th Street
1.6 km · 1 min · 12th Street
-
32
Turn right onto East Cumberland Avenue
1.3 km · 2 min · East Cumberland Avenue
-
33
Turn right onto 21st Street
155 m · 28 sec · 21st Street
-
34
Turn left onto Lothbury Avenue
53 m · 8 sec · Lothbury Avenue
-
35
Arrive at your destination
0 m · 1 sec · Lothbury Avenue
Car Route Details
A richer read on the saved driving route between Valley Station and Middlesboro.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
Cumberland Gap Parkway
Continue on Cumberland Gap Parkway
30.7 mi · 00h 37m
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 Valley Station and Sunny near Middlesboro.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Valley Station to Middlesboro?
The road trip is about 201 miles (323.4 km) and usually takes 03h 56m 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?
Stanford is a useful midpoint, sitting about 100.4 miles from Valley Station and 100.5 miles from Middlesboro.
How much longer is the road route than the straight-line distance?
The direct path is about 157.4 miles (253.3 km), while the road route adds roughly 43.6 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 9:06 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $26.74 one way or $53.47 round trip. Estimated CO2 is about 63 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Valley Station and Sunny near Middlesboro.
Flight Path Map
This map shows the direct air route between Valley Station and Middlesboro. Straight-line distance: 157.37 mi (253.27 km).
#1 Valley Station
Human settlement in Louisville, Kentucky, United States of America
| Population | 22,756 |
| Coordinates | 38.1111800, -85.8702400 |
| Altitude | 136 |
| 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: 323 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 06h 41m |
| 40 mph (64.37 km/h) | 05h 01m |
| 50 mph (80.47 km/h) | 04h 01m |
| 60 mph (96.56 km/h) | 03h 20m |
| 70 mph (112.65 km/h) | 02h 52m |
| 80 mph (129 km/h) | 02h 30m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $26.74 | $53.47 |
| Mid-grade | $4.25 | $30.15 | $60.31 |
| Premium | $4.65 | $33.00 | $65.99 |
| Diesel | $5.30 | $37.61 | $75.21 |
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.