How far is Owensboro, KY from Winchester, KY?
The driving distance from Owensboro, KY to Winchester, KY is about 199.3 miles (320.7 km), with a travel time of about 03h 48m by car.
- The straight-line flight distance is about 160.7 miles (258.6 km).
- For a round trip, plan for roughly 07h 36m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 AM CDT.
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 48m.
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.
County seat of Hardin County, 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 Owensboro and Winchester.
Turn-by-Turn Driving Directions
Step-by-step road directions between Owensboro and Winchester.
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1
Start on Frederica Street
1.1 mi · 2 min · Frederica Street
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2
Turn left onto West 18th Street
2675 ft · 1 min · West 18th Street
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3
Turn right onto Triplett Street
1156 ft · 28 sec · Triplett Street
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4
Turn straight onto New Hartford Road
1.9 mi · 3 min · New Hartford Road
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5
Turn left
1700 ft · 43 sec
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6
Merge slight left onto Wendell Ford Expressway
2274 ft · 30 sec · Wendell Ford Expressway
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7
Take the exit slight right toward I 165 South: Bowling Green
2273 ft · 56 sec
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8
Continue straight
28.8 mi · 31 min
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9
Take the exit slight right toward Elizabethtown
1772 ft · 50 sec
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10
Merge slight left onto Western Kentucky Parkway
60.1 mi · 1 hr 4 min · Western Kentucky Parkway
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11
Take the exit slight right toward I 65 North: Lexington, Louisville
1955 ft · 48 sec
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12
Keep slight left to continue on I 65 North: Lexington, Louisville
3052 ft · 1 min
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13
Merge slight left
1.4 mi · 1 min
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14
Take the exit slight right toward Lexington, Bardstown
3252 ft · 1 min
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15
Continue on Bluegrass Parkway
70.7 mi · 1 hr 16 min · Bluegrass Parkway
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16
Keep slight left to continue on US 60 West: Frankfort
571 ft · 16 sec
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17
Turn right onto Lexington Road
1.7 mi · 2 min · Lexington Road
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18
Continue on Versailles Road
4.6 mi · 6 min · Versailles Road
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19
Take the exit straight toward KY 4 North: New Circle Road
2735 ft · 1 min
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20
Merge slight left onto New Circle Road
5.7 mi · 8 min · New Circle Road
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21
Turn left onto North Broadway
1 mi · 2 min · North Broadway
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22
Turn left onto I 75 South, I 64 East: Knoxville, Ashland
2515 ft · 1 min
-
23
Merge slight left
1.6 mi · 2 min
-
24
Take the exit slight left toward I 64 East: Winchester, Ashland
13.2 mi · 15 min
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25
Take the exit slight right toward KY 1958 , KY 627 Truck Route South: Van Meter Road, Winchester
1267 ft · 31 sec
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26
Merge slight left onto Bypass Road
1158 ft · 17 sec · Bypass Road
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27
Turn left onto West Lexington Avenue
2 mi · 3 min · West Lexington Avenue
-
28
Turn right onto South Maple Street
832 ft · 21 sec · South Maple Street
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29
Turn left onto Boone Avenue
78 m · 10 sec · Boone Avenue
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30
Turn left onto Wall Alley
11 m · 3 sec · Wall Alley
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31
Arrive at your destination
0 m · 1 sec · Wall Alley
Car Route Details
A richer read on the saved driving route between Owensboro and Winchester.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Bluegrass Parkway
Continue on Bluegrass Parkway
70.7 mi · 01h 16m
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 Owensboro and Sunny near Winchester.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Owensboro to Winchester?
The road trip is about 199.3 miles (320.7 km) and usually takes 03h 48m 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?
Elizabethtown is a useful midpoint, sitting about 99.5 miles from Owensboro and 99.8 miles from Winchester.
How much longer is the road route than the straight-line distance?
The direct path is about 160.7 miles (258.6 km), while the road route adds roughly 38.6 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 CDT. If you want a more comfortable same-day return, try to leave by 9:24 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $26.51 one way or $53.02 round trip. Estimated CO2 is about 62.5 kg one way.
Do you cross a time zone on this route?
Yes. There is about a 1 hour time difference between Owensboro and Winchester, so arrival and return times should be read in local time.
What should you check before leaving?
Before you leave, expect Sunny around Owensboro and Sunny near Winchester.
Stop Ideas Near Elizabethtown
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 Elizabethtown.
Louisville, Kentucky
Flight Path Map
This map shows the direct air route between Owensboro and Winchester. Straight-line distance: 160.67 mi (258.58 km).
#1 Owensboro
The most populous city in Daviess County, Kentucky.
| Population | 60,344 |
| Coordinates | 37.7742200, -87.1133300 |
| Altitude | 120 |
| Country | United States |
#2 Winchester
City in and the county seat of Clark County, Kentucky, United States
| Population | 18,659 |
| Coordinates | 37.9900800, -84.1796500 |
| Altitude | 303 |
| Country | United States |
End: Winchester (-84.17965, 37.99008)
Estimated Travel Time
Distance: 321 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 06h 38m |
| 40 mph (64.37 km/h) | 04h 58m |
| 50 mph (80.47 km/h) | 03h 59m |
| 60 mph (96.56 km/h) | 03h 19m |
| 70 mph (112.65 km/h) | 02h 50m |
| 80 mph (129 km/h) | 02h 29m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $26.51 | $53.02 |
| Mid-grade | $4.25 | $29.90 | $59.80 |
| Premium | $4.65 | $32.72 | $65.44 |
| Diesel | $5.30 | $37.29 | $74.57 |
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.