How far is Henderson, KY from Winchester, KY?
The driving distance from Henderson, KY to Winchester, KY is about 219.7 miles (353.6 km), with a travel time of about 04h 12m by car.
- The straight-line flight distance is about 186.2 miles (299.7 km).
- For a round trip, plan for roughly 08h 25m 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 04h 12m.
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.
Sunny
Driving Route Map
The map below follows the saved road route between Henderson and Winchester.
Turn-by-Turn Driving Directions
Step-by-step road directions between Henderson and Winchester.
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1
Start on the route
30 m · 9 sec
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2
Turn right onto Washington Street
65 m · 10 sec · Washington Street
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3
Turn right onto South Green Street
1.6 mi · 4 min · South Green Street
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4
Take the ramp straight toward US 41: Evansville, Madisonville
748 ft · 21 sec
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5
Keep slight left to continue on US 41 North: Evansville
2451 ft · 1 min
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6
Merge slight left
5.3 mi · 8 min
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7
Take the exit slight right toward I 69 North
1008 ft · 17 sec
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8
Keep slight right to continue on I 69 North
1.2 km · 1 min
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9
Merge slight left
20 mi · 23 min
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10
Take the exit slight right toward I 64 East: Louisville
3069 ft · 58 sec
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11
Merge slight left
91.7 mi · 1 hr 40 min
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12
Keep slight right
83.1 mi · 1 hr 35 min
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13
Take the exit slight left toward I 64 East: Winchester, Ashland
13.2 mi · 15 min
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14
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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15
Merge slight left onto Bypass Road
1158 ft · 17 sec · Bypass Road
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16
Turn left onto West Lexington Avenue
2 mi · 3 min · West Lexington Avenue
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17
Turn right onto South Maple Street
832 ft · 21 sec · South Maple Street
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18
Turn left onto Boone Avenue
78 m · 10 sec · Boone Avenue
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19
Turn left onto Wall Alley
11 m · 3 sec · Wall Alley
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20
Arrive at your destination
0 m · 1 sec · Wall Alley
Car Route Details
A richer read on the saved driving route between Henderson 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.
I 64 East
Merge slight left
91.7 mi · 01h 40m
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 Henderson and Sunny near Winchester.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Henderson to Winchester?
The road trip is about 219.7 miles (353.6 km) and usually takes 04h 12m 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 109.7 miles from Henderson and 110 miles from Winchester.
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 33.5 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 8:34 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $29.23 one way or $58.45 round trip. Estimated CO2 is about 68.9 kg one way.
Do you cross a time zone on this route?
Yes. There is about a 1 hour time difference between Henderson 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 Henderson and Sunny near Winchester.
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 Henderson and Winchester. Straight-line distance: 186.19 mi (299.65 km).
#1 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 |
#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: 354 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 07h 19m |
| 40 mph (64.37 km/h) | 05h 29m |
| 50 mph (80.47 km/h) | 04h 23m |
| 60 mph (96.56 km/h) | 03h 39m |
| 70 mph (112.65 km/h) | 03h 08m |
| 80 mph (129 km/h) | 02h 44m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $29.23 | $58.45 |
| Mid-grade | $4.25 | $32.96 | $65.92 |
| Premium | $4.65 | $36.07 | $72.14 |
| Diesel | $5.30 | $41.11 | $82.21 |
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.