How far is Leesburg, VA from Winchester, VA?
The driving distance from Leesburg, VA to Winchester, VA is about 35.4 miles (57 km), with a travel time of about 00h 53m by car.
- The straight-line flight distance is about 32.5 miles (52.3 km).
- For a round trip, plan for roughly 01h 47m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
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 00h 53m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
This departure sits inside the recommended comfort window for the route.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Town in Virginia, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Leesburg and Winchester.
Turn-by-Turn Driving Directions
Step-by-step road directions between Leesburg and Winchester.
-
1
Start on East Market Street
1 mi · 3 min · East Market Street
-
2
Take the ramp straight toward VA 7 West: Winchester
875 ft · 30 sec
-
3
Merge slight left onto Leesburg Pike
15.5 mi · 21 min · Leesburg Pike
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4
Continue on Harry Byrd Highway
13.6 mi · 19 min · Harry Byrd Highway
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5
Continue on Berryville Pike
3.6 mi · 6 min · Berryville Pike
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6
Continue on Berryville Avenue
1.4 km · 2 min · Berryville Avenue
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7
Continue on National Avenue
1997 ft · 1 min · National Avenue
-
8
Turn left onto East Lane
73 m · 7 sec · East Lane
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9
Enter the roundabout and take exit 1 toward East Piccadilly Street
19 m · 1 sec · East Piccadilly Street
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10
Exit the roundabout onto East Piccadilly Street
751 ft · 35 sec · East Piccadilly Street
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11
Turn left onto North Cameron Street
38 m · 4 sec · North Cameron Street
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12
Arrive at your destination
0 m · 1 sec · North Cameron Street
Car Route Details
A richer read on the saved driving route between Leesburg and Winchester.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
Leesburg Pike
Merge slight left onto Leesburg Pike
15.5 mi · 00h 21m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Sunny leaving Leesburg and Mostly Sunny near Winchester.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Leesburg to Winchester?
The road trip is about 35.4 miles (57 km) and usually takes 00h 53m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Berryville is a useful midpoint, sitting about 17.6 miles from Leesburg and 17.8 miles from Winchester.
How much longer is the road route than the straight-line distance?
The direct path is about 32.5 miles (52.3 km), while the road route adds roughly 2.9 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 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 4:42 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $4.95 one way or $9.90 round trip. Estimated CO2 is about 11.1 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Leesburg and Mostly Sunny near Winchester.
Stop Ideas Near Berryville
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 Berryville.
Harpers Ferry
Martinsburg station
Frederick, MD
Hagerstown, MD
Flight Path Map
This map shows the direct air route between Leesburg and Winchester. Straight-line distance: 32.5 mi (52.3 km).
#1 Leesburg
Historic town within and the county seat of Loudoun County, Virginia, United States
| Population | 54,488 |
| Coordinates | 39.1156600, -77.5636000 |
| Altitude | 104 |
| Country | United States |
#2 Winchester
Independent city in Virginia, United States
| Population | 27,700 |
| Coordinates | 39.1856600, -78.1633300 |
| Altitude | 216 |
| Country | United States |
End: Winchester (-78.16333, 39.18566)
Estimated Travel Time
Distance: 57 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 10m |
| 40 mph (64.37 km/h) | 00h 53m |
| 50 mph (80.47 km/h) | 00h 42m |
| 60 mph (96.56 km/h) | 00h 35m |
| 70 mph (112.65 km/h) | 00h 30m |
| 80 mph (129 km/h) | 00h 26m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $4.95 | $9.90 |
| Mid-grade | $4.43 | $5.54 | $11.07 |
| Premium | $4.78 | $5.97 | $11.94 |
| Diesel | $5.62 | $7.03 | $14.06 |
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 Virginia · May 19, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.