How far is Winchester, VA from Charlottesville, VA?
The driving distance from Winchester, VA to Charlottesville, VA is about 99.9 miles (160.7 km), with a travel time of about 02h 09m by car.
- The straight-line flight distance is about 81.6 miles (131.4 km).
- For a round trip, plan for roughly 04h 18m 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 02h 09m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
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.
Village in Virginia
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 Winchester and Charlottesville.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winchester and Charlottesville.
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1
Start on North Cameron Street
742 ft · 33 sec · North Cameron Street
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2
Turn left onto East Boscawen Street
130 m · 16 sec · East Boscawen Street
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3
Turn right onto South Kent Street
3092 ft · 1 min · South Kent Street
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4
Turn left onto Millwood Avenue
1.2 km · 2 min · Millwood Avenue
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5
Turn left onto Millwood Avenue
1192 ft · 42 sec · Millwood Avenue
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6
Take the ramp slight right toward I 81 South: Roanoke
1605 ft · 24 sec
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7
Merge slight left
12.6 mi · 14 min
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8
Take the exit slight left toward I 66 East: Front Royal, Washington
3068 ft · 1 min
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9
Continue straight
6.3 mi · 7 min
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10
Take the exit slight right toward US 340, US 522: Winchester, Front Royal
613 ft · 15 sec
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11
Keep slight right
559 ft · 14 sec
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12
Turn straight onto Winchester Road
1.4 km · 2 min · Winchester Road
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13
Continue on North Shenandoah Avenue
1.4 mi · 3 min · North Shenandoah Avenue
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14
At the end of the road, turn left onto Kendrick Lane
1123 ft · 22 sec · Kendrick Lane
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15
Continue on West 6th Street
1178 ft · 29 sec · West 6th Street
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16
Turn right onto North Commerce Avenue
1.2 mi · 3 min · North Commerce Avenue
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17
Continue on Remount Road
4.7 mi · 7 min · Remount Road
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18
Continue on Zachary Taylor Highway
10.1 mi · 15 min · Zachary Taylor Highway
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19
Turn right onto Lee Highway
8.1 mi · 11 min · Lee Highway
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20
Turn left onto Sperryville Pike
543 ft · 24 sec · Sperryville Pike
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21
At the end of the road, turn left onto Sperryville Pike
1.1 km · 1 min · Sperryville Pike
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22
Turn right onto F.T. Valley Road
8.2 mi · 11 min · F.T. Valley Road
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23
Continue on South F T Valley Road
7.1 mi · 11 min · South F T Valley Road
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24
Continue on North Blue Ridge Turnpike
5.4 mi · 8 min · North Blue Ridge Turnpike
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25
Continue on North Main Street
1.3 mi · 2 min · North Main Street
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26
Merge slight left onto South Seminole Trail
1.3 mi · 2 min · South Seminole Trail
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27
Continue straight
23.3 mi · 34 min
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28
Turn left onto Hydraulic Road
1022 ft · 32 sec · Hydraulic Road
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29
Enter the roundabout and take exit 1 toward Hydraulic Road
29 m · 3 sec · Hydraulic Road
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30
Exit the roundabout onto Hydraulic Road
1252 ft · 33 sec · Hydraulic Road
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31
Turn left onto U.S. 250 Bypass
1.5 mi · 3 min · U.S. 250 Bypass
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32
Take the exit slight right toward Park Street
147 m · 20 sec
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33
Turn right onto Park Street
1 km · 2 min · Park Street
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34
Turn left onto East High Street
96 m · 13 sec · East High Street
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35
Turn right onto 7th Street Northeast
873 ft · 44 sec · 7th Street Northeast
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36
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Winchester and Charlottesville.
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.
South Seminole Trail
Continue straight
23.3 mi · 00h 34m
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 Winchester and Sunny near Charlottesville.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winchester to Charlottesville?
The road trip is about 99.9 miles (160.7 km) and usually takes 02h 09m 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?
Washington is a useful midpoint, sitting about 49.4 miles from Winchester and 50.5 miles from Charlottesville.
How much longer is the road route than the straight-line distance?
The direct path is about 81.6 miles (131.4 km), while the road route adds roughly 18.3 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 2:12 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $13.94 one way or $27.89 round trip. Estimated CO2 is about 31.3 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Winchester and Sunny near Charlottesville.
Stop Ideas Near Washington
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 Washington.
Culpeper station
Manassas station
Burke Centre
Fredericksburg
Flight Path Map
This map shows the direct air route between Winchester and Charlottesville. Straight-line distance: 81.67 mi (131.43 km).
#1 Winchester
Independent city in Virginia, United States
| Population | 27,700 |
| Coordinates | 39.1856600, -78.1633300 |
| Altitude | 216 |
| Country | United States |
#2 Charlottesville
The capital of Virginia.
| Population | 46,950 |
| Coordinates | 38.0293100, -78.4766800 |
| Altitude | 142 |
| Country | United States |
End: (-78.476567, 38.029526)
Estimated Travel Time
Distance: 161 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 19m |
| 40 mph (64.37 km/h) | 02h 29m |
| 50 mph (80.47 km/h) | 01h 59m |
| 60 mph (96.56 km/h) | 01h 39m |
| 70 mph (112.65 km/h) | 01h 25m |
| 80 mph (129 km/h) | 01h 14m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $13.94 | $27.89 |
| Mid-grade | $4.43 | $15.59 | $31.18 |
| Premium | $4.78 | $16.82 | $33.64 |
| Diesel | $5.62 | $19.80 | $39.59 |
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 · 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.