How far is Winchester, KY from Henderson, KY?
The driving distance from Winchester, KY to Henderson, KY is about 221.8 miles (357 km), with a travel time of about 03h 30m by car.
- The straight-line flight distance is about 186.2 miles (299.7 km).
- For a round trip, plan for roughly 07h 00m 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 30m.
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 Jefferson County, Kentucky, United States of America
Route Weather Snapshot
Check the forecast at both ends before you head out.
Slight Chance Showers And Thunderstorms then Mostly Sunny
Sunny
Driving Route Map
The map below follows the saved road route between Winchester and Henderson.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winchester and Henderson.
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1
Start on Wall Alley
11 m · 5 sec · Wall Alley
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2
Turn right onto Boone Avenue
78 m · 9 sec · Boone Avenue
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3
Turn right onto Maple Street
832 ft · 21 sec · Maple Street
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4
Turn left onto West Lexington Avenue
2 mi · 3 min · West Lexington Avenue
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5
Turn right onto Bypass Road
1941 ft · 36 sec · Bypass Road
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6
Take the exit left
1360 ft · 33 sec
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7
Merge slight left
12.1 mi · 13 min
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8
Keep slight right to continue on I 64 West, I 75 North: Louisville, Cincinnati
6.9 mi · 8 min
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9
Keep slight left to continue on I 64 West: Frankfort, Louisville
73.5 mi · 1 hr 23 min
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10
Keep slight right
5.3 mi · 7 min
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11
Continue straight
90.4 mi · 1 hr 38 min
-
12
Take the exit slight right toward I 69 South, SR 57 South: Evansville, Henderson, Kentucky
1463 ft · 50 sec
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13
Merge slight left
20.1 mi · 23 min
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14
Take the exit slight right toward US 41: Vincennes, Henderson, Kentucky
884 ft · 17 sec
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15
Keep slight left to continue on US 41 South: Henderson, Kentucky
2455 ft · 47 sec
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16
Keep slight right to continue on US 41 South: Henderson, Kentucky
789 ft · 27 sec
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17
Keep slight right to continue on US 41 South: Henderson, Kentucky
1353 ft · 46 sec
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18
Merge slight left
6.1 mi · 9 min
-
19
Take the exit slight right toward US 60 West, US 41 Alternate: Henderson
1305 ft · 36 sec
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20
Turn straight
1.6 mi · 4 min
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21
Turn left onto Washington Street
65 m · 11 sec · Washington Street
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22
Turn left
30 m · 7 sec
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23
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Winchester and Henderson.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
I 64 West
Continue straight
90.4 mi · 01h 38m
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.
Slight Chance Showers And Thunderstorms then Mostly Sunny leaving Winchester and Sunny near Henderson.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winchester to Henderson?
The road trip is about 221.8 miles (357 km) and usually takes 03h 30m 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?
Saint Dennis is a useful midpoint, sitting about 110 miles from Winchester and 111.7 miles from Henderson.
How much longer is the road route than the straight-line distance?
The direct path is about 186.2 miles (299.7 km), while the road route adds roughly 35.6 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 10:00 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $29.53 one way or $59.05 round trip. Estimated CO2 is about 69.6 kg one way.
Do you cross a time zone on this route?
Yes. There is about a 1 hour time difference between Winchester and Henderson, so arrival and return times should be read in local time.
What should you check before leaving?
Before you leave, expect Slight Chance Showers And Thunderstorms then Mostly Sunny around Winchester and Sunny near Henderson.
Stop Ideas Near Saint Dennis
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 Saint Dennis.
Louisville, Kentucky
Flight Path Map
This map shows the direct air route between Winchester and Henderson. Straight-line distance: 186.19 mi (299.65 km).
#1 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 |
#2 Henderson
City in and county seat of Henderson County, Kentucky, United States
| Population | 27,974 |
| Coordinates | 37.8361500, -87.5900100 |
| Altitude | 124 |
| Country | United States |
End: (-87.590062, 37.836125)
Estimated Travel Time
Distance: 357 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 07h 23m |
| 40 mph (64.37 km/h) | 05h 32m |
| 50 mph (80.47 km/h) | 04h 26m |
| 60 mph (96.56 km/h) | 03h 41m |
| 70 mph (112.65 km/h) | 03h 10m |
| 80 mph (129 km/h) | 02h 46m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $29.53 | $59.05 |
| Mid-grade | $4.25 | $33.30 | $66.60 |
| Premium | $4.65 | $36.44 | $72.88 |
| Diesel | $5.30 | $41.53 | $83.06 |
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.