How far is Windsor, VA from Chesapeake, VA?
The driving distance from Windsor, VA to Chesapeake, VA is about 81.8 miles (131.6 km), with a travel time of about 01h 29m by car.
- The straight-line flight distance is about 70.3 miles (113.1 km).
- For a round trip, plan for roughly 02h 59m 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 01h 29m.
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.
Independent city in Virginia, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny then Slight Chance Rain Showers
Driving Route Map
The map below follows the saved road route between Windsor and Chesapeake.
Turn-by-Turn Driving Directions
Step-by-step road directions between Windsor and Chesapeake.
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1
Start on Gaardahl Drive
78 m · 13 sec · Gaardahl Drive
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2
Turn right onto Rasmussen Drive
154 m · 24 sec · Rasmussen Drive
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3
Turn right onto Stockholm Drive
2620 ft · 2 min · Stockholm Drive
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4
Turn left onto White Oak Road
2780 ft · 1 min · White Oak Road
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5
At the end of the road, turn right onto East Williamsburg Road
1011 ft · 16 sec · East Williamsburg Road
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6
Continue on Pocahontas Trail
1.2 km · 1 min · Pocahontas Trail
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7
Turn left onto New Kent Highway
901 ft · 17 sec · New Kent Highway
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8
Take the ramp slight right toward I 64 East, VA 33 East: West Point, Norfolk
63.2 mi · 1 hr 11 min
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9
Keep slight left to continue on Hampton Roads Beltway
104 m · 5 sec · Hampton Roads Beltway
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10
Continue on Hampton Roads Bridge-Tunnel
3.5 mi · 5 min · Hampton Roads Bridge-Tunnel
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11
Continue on Hampton Roads Beltway
6.7 mi · 9 min · Hampton Roads Beltway
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12
Take the exit slight right toward VA 194 South: Chesapeake Boulevard
1312 ft · 32 sec
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13
Turn straight onto Chesapeake Boulevard
2.1 mi · 3 min · Chesapeake Boulevard
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14
Turn straight
41 m · 8 sec
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15
Turn left onto Ballentine Boulevard
1.1 mi · 2 min · Ballentine Boulevard
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16
Turn right onto East Princess Anne Road
1.5 km · 2 min · East Princess Anne Road
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17
Turn left onto Park Avenue
3186 ft · 1 min · Park Avenue
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18
Turn left onto East Brambleton Avenue
1692 ft · 58 sec · East Brambleton Avenue
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19
Continue on Campostella Road
1.1 km · 2 min · Campostella Road
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20
Turn right onto Wilson Road
1.2 km · 1 min · Wilson Road
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21
Continue on 22nd Street
1606 ft · 27 sec · 22nd Street
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22
Continue on Poindexter Street
1391 ft · 29 sec · Poindexter Street
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23
Turn right onto D Street
126 m · 18 sec · D Street
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24
Arrive at your destination
0 m · 1 sec · D Street
Car Route Details
A richer read on the saved driving route between Windsor and Chesapeake.
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
Take the ramp slight right toward I 64 East, VA 33 East: West Point, Norfolk
63.2 mi · 01h 11m
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.
Mostly Sunny then Slight Chance Rain Showers leaving Windsor and Sunny near Chesapeake.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Windsor to Chesapeake?
The road trip is about 81.8 miles (131.6 km) and usually takes 01h 29m 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?
Williamsburg is a useful midpoint, sitting about 41.5 miles from Windsor and 40.2 miles from Chesapeake.
How much longer is the road route than the straight-line distance?
The direct path is about 70.3 miles (113.1 km), while the road route adds roughly 11.5 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 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 3:30 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $11.41 one way or $22.82 round trip. Estimated CO2 is about 25.6 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny then Slight Chance Rain Showers around Windsor and Sunny near Chesapeake.
Stop Ideas Near Williamsburg
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Oxford Run Trail
James City County
Poquoson (DMV Select) By Appointment Only
Legacy Hall
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Williamsburg.
Williamsburg Transportation Center
Newport News station
Norfolk
Petersburg station
Flight Path Map
This map shows the direct air route between Windsor and Chesapeake. Straight-line distance: 70.3 mi (113.14 km).
#1 Windsor
Town in southeastern Virginia, United States
| Population | 2,800 |
| Coordinates | 37.5054200, -77.2174700 |
| Altitude | 41 |
| Country | United States |
#2 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
End: D Street (-76.275044, 36.81897)
Estimated Travel Time
Distance: 132 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 43m |
| 40 mph (64.37 km/h) | 02h 02m |
| 50 mph (80.47 km/h) | 01h 38m |
| 60 mph (96.56 km/h) | 01h 21m |
| 70 mph (112.65 km/h) | 01h 10m |
| 80 mph (129 km/h) | 01h 01m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $11.41 | $22.82 |
| Mid-grade | $4.43 | $12.76 | $25.51 |
| Premium | $4.78 | $13.76 | $27.52 |
| Diesel | $5.62 | $16.20 | $32.39 |
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 17, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.