How far is Portsmouth, VA from Winchester, VA?
The driving distance from Portsmouth, VA to Winchester, VA is about 225.5 miles (362.9 km), with a travel time of about 04h 45m by car.
- The straight-line flight distance is about 191.5 miles (308.2 km).
- For a round trip, plan for roughly 09h 30m 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 04h 45m.
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.
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 Portsmouth and Winchester.
Turn-by-Turn Driving Directions
Step-by-step road directions between Portsmouth and Winchester.
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1
Start on High Street
2505 ft · 56 sec · High Street
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2
Turn right onto Effingham Street
552 ft · 11 sec · Effingham Street
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3
Turn left onto London Boulevard
1.1 mi · 2 min · London Boulevard
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4
Take the ramp slight right toward US 58, VA 164: Western Freeway, Midtown Tunnel
996 ft · 19 sec
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5
Merge slight left onto Martin Luther King Freeway
1826 ft · 35 sec · Martin Luther King Freeway
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6
Continue on Western Freeway
6 mi · 8 min · Western Freeway
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7
Take the exit slight right toward VA 135: College Drive
1030 ft · 15 sec
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8
Keep slight right to continue on VA 135 North: College Drive
738 ft · 10 sec
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9
Turn straight onto College Drive
1.1 mi · 2 min · College Drive
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10
Take the ramp slight right toward I 664 North: Newport News, Hampton
2371 ft · 58 sec
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11
Merge slight left onto Hampton Roads Beltway
1.3 km · 1 min · Hampton Roads Beltway
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12
Continue on Monitor-Merrimac Memorial Bridge-Tunnel
4.3 mi · 5 min · Monitor-Merrimac Memorial Bridge-Tunnel
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13
Continue on Hampton Roads Beltway
6.2 mi · 8 min · Hampton Roads Beltway
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14
Keep slight left to continue on I 64 West: Williamsburg, Richmond
1.1 km · 54 sec
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15
Merge slight left
1.4 mi · 2 min
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16
Keep slight left
61.1 mi · 1 hr 8 min
-
17
Take the exit slight right toward I 295, US 60: Washington, Rocky Mount NC
2434 ft · 32 sec
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18
Keep slight right to continue on I 295 North: Washington
1.3 mi · 3 min
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19
Merge slight left onto Korean War Veterans Memorial Highway
11.9 mi · 13 min · Korean War Veterans Memorial Highway
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20
Take the exit slight left toward I 95 North: Washington
2.4 mi · 3 min
-
21
Merge slight right
45.7 mi · 50 min
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22
Keep slight right
1.6 mi · 2 min
-
23
Keep slight right to continue on US 17 Business: Falmouth
1635 ft · 42 sec
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24
Turn left onto Warrenton Road
22.9 mi · 33 min · Warrenton Road
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25
Continue on Marsh Road
4.2 mi · 7 min · Marsh Road
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26
Turn right onto James Madison Highway
4.6 mi · 6 min · James Madison Highway
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27
Continue on Eastern Bypass
2.4 mi · 3 min · Eastern Bypass
-
28
Keep slight right to continue on Eastern Bypass
2.3 mi · 3 min · Eastern Bypass
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29
Continue on James Madison Highway
6.7 mi · 9 min · James Madison Highway
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30
Continue on Winchester Road
2.7 mi · 4 min · Winchester Road
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31
Turn left
4.8 mi · 5 min
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32
Take the exit slight right toward US 17 North: Delaplane, Paris
8.1 mi · 14 min
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33
At the end of the road, turn left onto John Singleton Mosby Highway
8.9 mi · 13 min · John Singleton Mosby Highway
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34
Continue on John Mosby Highway
2.1 mi · 3 min · John Mosby Highway
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35
Continue on Millwood Pike
5.7 mi · 9 min · Millwood Pike
-
36
Continue on Millwood Avenue
832 ft · 20 sec · Millwood Avenue
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37
Continue on Millwood Avenue
1.2 km · 2 min · Millwood Avenue
-
38
Turn right onto South Kent Street
3092 ft · 2 min · South Kent Street
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39
Turn left onto East Boscawen Street
130 m · 18 sec · East Boscawen Street
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40
Turn right onto North Cameron Street
742 ft · 25 sec · North Cameron Street
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41
Arrive at your destination
0 m · 1 sec · North Cameron Street
Car Route Details
A richer read on the saved driving route between Portsmouth 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 West
Keep slight left
61.1 mi · 01h 08m
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 Portsmouth 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 Portsmouth to Winchester?
The road trip is about 225.5 miles (362.9 km) and usually takes 04h 45m 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?
Ashland is a useful midpoint, sitting about 112.8 miles from Portsmouth and 112.7 miles from Winchester.
How much longer is the road route than the straight-line distance?
The direct path is about 191.5 miles (308.2 km), while the road route adds roughly 34 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 7:30 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $31.53 one way or $63.06 round trip. Estimated CO2 is about 70.7 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Portsmouth and Mostly Sunny near Winchester.
Stop Ideas Near Ashland
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 Ashland.
Ashland
Richmond Staples Mill Road station
Richmond Main Street Station
Petersburg station
Flight Path Map
This map shows the direct air route between Portsmouth and Winchester. Straight-line distance: 191.5 mi (308.19 km).
#1 Portsmouth
The most populous city in Portsmouth, Virginia.
| Population | 95,094 |
| Coordinates | 36.8354300, -76.2982700 |
| Altitude | 3 |
| 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: 363 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 07h 30m |
| 40 mph (64.37 km/h) | 05h 38m |
| 50 mph (80.47 km/h) | 04h 30m |
| 60 mph (96.56 km/h) | 03h 45m |
| 70 mph (112.65 km/h) | 03h 13m |
| 80 mph (129 km/h) | 02h 48m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $31.53 | $63.06 |
| Mid-grade | $4.43 | $35.25 | $70.51 |
| Premium | $4.78 | $38.03 | $76.07 |
| Diesel | $5.62 | $44.77 | $89.53 |
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.