Drive Time
1h 29m
Distance
81.7 mi
132 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$13
one way
Photo: Willians Huerta
The drive from Windsor, VA to Chesapeake, VA covers 81.7 miles and takes about 1h 29m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Rasmussen Drive, Stockholm Drive, White Oak Road for much of the mileage, and the overall profile is turn-heavy local drive. At current regular gas prices, budget about $12.74 one way before food or hotel costs.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Break Rhythm
0 planned breaks
A short stop every 2 to 3 hours is enough for this drive.
Midpoint
40.9 miles from Windsor, VA
A natural place for your longest stop of the day , about 44m into the drive .
Expect a 1h 29m drive with frequent turns across 81.7 miles of local and secondary roads.
| Road | Distance | Duration |
|---|---|---|
| Rasmussen Drive | Unavailable | Refreshing |
| Stockholm Drive | Unavailable | Refreshing |
| White Oak Road | Unavailable | Refreshing |
| East Williamsburg Road | Unavailable | Refreshing |
| Pocahontas Trail | Unavailable | Refreshing |
| New Kent Highway | Unavailable | Refreshing |
| I 64 East | Unavailable | Refreshing |
| Hampton Roads Beltway | Unavailable | Refreshing |
Per-road distance and duration are being refreshed from OSRM for this route.
Step-by-step road directions between Windsor, VA and Chesapeake, VA.
Start on Gaardahl Drive
Turn right onto Rasmussen Drive
Turn right onto Stockholm Drive
Turn left onto White Oak Road
At the end of the road, turn right onto East Williamsburg Road
Continue on Pocahontas Trail
Turn left onto New Kent Highway
Take the ramp slight right toward I 64 East, VA 33 East: West Point, Norfolk
Keep slight left to continue on Hampton Roads Beltway
Continue on Hampton Roads Bridge-Tunnel
Continue on Hampton Roads Beltway
Take the exit slight right toward VA 194 South: Chesapeake Boulevard
Turn straight onto Chesapeake Boulevard
Turn straight
Turn left onto Ballentine Boulevard
Turn right onto East Princess Anne Road
Turn left onto Park Avenue
Turn left onto East Brambleton Avenue
Continue on Campostella Road
Turn right onto Wilson Road
Continue on 22nd Street
Continue on Poindexter Street
Turn right onto D Street
Arrive at your destination
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 80 miles or 1h 27m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 40.9 miles or 44m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 16m
Traffic, exits, and arrival timing usually matter more near Chesapeake, VA than in the middle of the route.
Open the route before leaving Windsor, VA so your first major turns are already loaded.
Leave with enough water and a charging cable within reach, not packed away.
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Windsor, VA
This is one driving day of about 81.7 miles and 1h 29m.
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 40.9 mi from Windsor, VA · 44m into the drive
Mid-route town
Meal stop
41 mi into the route
Best for: Lunch, fuel, and a longer reset
This sits close to the middle of the route, so it works well for the longest stop of the day.
A short stop after about 80 miles helps settle the day before fatigue starts building.
The midpoint is around 40.9 miles from Windsor, VA, which is a good place for a longer meal and fuel stop.
The final approach into Chesapeake, VA usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Chesapeake, VA.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Regular Gas
$12.74 one way
$25.48 round trip
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.43 | $14.25 | $28.49 |
| premium | $4.78 | $15.37 | $30.74 |
| diesel | $5.62 | $18.09 | $36.18 |
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$13
Meals
$25–$50
Total
$38–$63
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 28.6 kg one way.
Driving Electric?
About $9 in charging · 0 stops · 66% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 24.5 | 0 | $8.58 | $3.92 |
| Efficient EV | 20.4 | 0 | $7.15 | $3.27 |
| EV Truck/SUV | 32.7 | 0 | $11.44 | $5.23 |
Gas CO2
29 kg
EV CO2
10 kg (66% less)
This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive. If you're planning ahead, check the forecast closer to your travel date.
Origin
Morning in Windsor on Saturday
Local time
11:38 AM
EDT
Current temp
67°F
Forecast unavailable right now
Destination
Morning in Chesapeake on Saturday
Local time
11:38 AM
EDT
Current temp
67°F
Forecast unavailable right now
Along the Route
84°F
Princess Anne, MD
41 mi in
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
Both ends of the route are sitting at about the same temperature right now.
Road read
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
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