Origin
Windsor, VA
Evening in Windsor on Wednesday
Local time
7:09 PM
EDT
Current temp
72°F
Unavailable
Live forecast
Trip from Windsor, VA to Chesapeake, VA
Last recalculated Apr 15, 2026
Drive Time
1h 45m
Distance
83.1 mi
134 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$13
one way
Best Time to Leave
4 AM
1h 37m
★
6 AM
1h 45m
8 AM
2h 1m
10 AM
1h 51m
12 PM
1h 49m
3 PM
1h 51m
5 PM
2h 0m
8 PM
1h 40m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Windsor, VA
Wikimedia Commons
Chesapeake, VA
Wikimedia Commons
Trip Overview
If you are planning a trip from Windsor to Chesapeake, you can expect an 83.1-mile journey that typically takes about 1 hour and 45 minutes to complete. This route is designed as a single-day trip, making it an efficient choice for those looking to travel between these two Southeast Virginia locations without the need for an overnight stay. With a fuel budget of approximately $13, the drive is quite economical for a solo traveler or a small group. You will spend the vast majority of your time on major thoroughfares, as the route is heavily highway-focused. Whether you are commuting or heading out for a quick excursion, this straightforward drive provides a reliable connection across the region.
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
41.6 miles from Windsor, VA
A natural place for your longest stop of the day , about 52m into the drive .
Drive Character
The personality of this drive is defined by a significant highway share of 76%, ensuring you spend most of your time at cruising speeds. You will navigate a mix of VA 33, the Hampton Roads Beltway, and the Hampton Roads Bridge-Tunnel as you make your way toward your destination. The longest uninterrupted stretch covers 63.2 miles along VA 33, which serves as the backbone of your journey. Expect the character of the road to shift as you transition from more rural stretches onto the high-traffic corridors of the beltway and tunnel system. Behind the wheel, you should prepare for a consistent, fast-paced experience that requires steady attention to changing traffic patterns.
This route has more turning and local-road decision points than a simple highway run.
There are about 24 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Rasmussen Drive is one of the defining roads on this drive.
How Hard Is This Drive?
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. Navigation is very simple - set it and forget it for most of the drive.
Route Complexity
1/10
Very easy - short and simple to drive
The drive from Windsor, VA to Chesapeake, VA is easy. At 1h 45m with 0% highway, most drivers will find it relaxed and low-stress.
Where does it get tricky?
This route does not have any notably tricky sections. Most of the drive from Windsor, VA to Chesapeake, VA is straightforward, with well-signed roads and simple exits.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Rasmussen Drive | — | — |
| Stockholm Drive | — | — |
| White Oak Road | — | — |
| East Williamsburg Road | — | — |
| Pocahontas Trail | — | — |
| New Kent Highway | — | — |
| I 64 East | — | — |
| Hampton Roads Beltway | — | — |
Some road-level metrics are being recalculated.
Longest stretch:
Rasmussen Drive
— detailed segment metrics are refreshing.
Turn-by-Turn Driving Directions
Step-by-step road directions between Windsor, VA and Chesapeake, VA.
1
Start on Gaardahl Drive
256 ft
·
13 sec
·
Gaardahl Drive
2
Turn right onto Rasmussen Drive
505 ft
·
24 sec
·
Rasmussen Drive
3
Turn right onto Stockholm Drive
0.5 mi
·
1 min
·
Stockholm Drive
4
Turn left onto White Oak Road
0.5 mi
·
1 min
·
White Oak Road
5
At the end of the road, turn right onto East Williamsburg Road
0.2 mi
·
16 sec
·
East Williamsburg Road
6
Continue on Pocahontas Trail
0.7 mi
·
1 min
·
Pocahontas Trail
7
Turn left onto New Kent Highway
0.2 mi
·
17 sec
·
New Kent Highway
8
Take the ramp slight right toward I 64 East, VA 33 East: West Point, Norfolk
63 mi
·
1 hr 11 min
·
I 64 East, VA 33 East: West Point, Norfolk
9
Keep slight left to continue on Hampton Roads Beltway
341 ft
·
5 sec
·
Hampton Roads Beltway
10
Continue on Hampton Roads Bridge-Tunnel
3.5 mi
·
4 min
·
Hampton Roads Bridge-Tunnel
11
Continue on Hampton Roads Beltway
6.7 mi
·
8 min
·
Hampton Roads Beltway
12
Take the exit slight right toward VA 194 South: Chesapeake Boulevard
0.2 mi
·
32 sec
·
VA 194 South: Chesapeake Boulevard
13
Turn straight onto Chesapeake Boulevard
2.1 mi
·
3 min
·
Chesapeake Boulevard
14
Turn straight
135 ft
·
8 sec
15
Turn left onto Ballentine Boulevard
1.1 mi
·
1 min
·
Ballentine Boulevard
16
Turn right onto East Princess Anne Road
0.9 mi
·
1 min
·
East Princess Anne Road
17
Turn left onto Park Avenue
0.6 mi
·
1 min
·
Park Avenue
18
Turn left onto East Brambleton Avenue
0.3 mi
·
58 sec
·
East Brambleton Avenue
19
Continue on Campostella Road
0.7 mi
·
1 min
·
Campostella Road
20
Turn right onto Wilson Road
0.7 mi
·
1 min
·
Wilson Road
21
Continue on 22nd Street
0.3 mi
·
27 sec
·
22nd Street
22
Continue on Poindexter Street
0.3 mi
·
29 sec
·
Poindexter Street
23
Turn right onto D Street
413 ft
·
18 sec
·
D Street
24
Arrive at your destination
Trip Plan
Because this is a relatively short 1 hour and 45-minute drive, you have plenty of flexibility in your departure schedule. Since the route involves major infrastructure like the Hampton Roads Bridge-Tunnel, it is wise to check for tunnel traffic or roadwork updates before you pull out of Windsor. You won't need to plan for any formal stops along the way given the manageable distance, though keeping your fuel levels monitored for the $13 estimate remains a good best practice. Use the lack of required stops to your advantage by timing your departure to avoid the heaviest regional commute hours. Staying alert while navigating the high-speed transitions between VA 33 and the Hampton Roads Beltway will help ensure you reach Chesapeake smoothly.
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.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 41.6 miles from Windsor, VA, or about 52m into the drive.
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 18 miles or 22m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 41.6 miles or 52m 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 29m
Traffic, exits, and arrival timing usually matter more near Chesapeake, VA than in the middle of the route.
Before You Leave
+
Open the route before leaving Windsor, VA so your first major turns are already loaded.
Day 1
Settle into the route from Windsor, VA
This is one driving day of about 83.1 miles and 1h 45m.
Your first comfortable stop window is around 18 miles from Windsor, VA.
This route can stay practical as a one-day drive if traffic stays reasonable.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 41.6 mi from Windsor, VA · 52m into the drive
Mid-route town
Meal stop
42 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.
Pacing Suggestions
Fuel and coffee
A short stop after about 18 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 41.6 miles from Windsor, VA, which is a good place for a longer meal and fuel stop.
Arriving in Chesapeake, VA
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.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Fuel & Cost
Regular Gas
$13.00 one way
$25.99 round trip
$3.97/gal
25.4 MPG avg
29 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.34 | $14.21 | $28.42 |
| premium | $4.70 | $15.38 | $30.76 |
| diesel | $5.61 | $18.35 | $36.69 |
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: 29.1 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $9 in charging · 0 stops · 66% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 24.9 | 0 | $8.73 | $3.99 |
| Efficient EV | 20.8 | 0 | $7.27 | $3.32 |
| EV Truck/SUV | 33.2 | 0 | $11.63 | $5.32 |
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.
Destination
Chesapeake, VA
Evening in Chesapeake on Wednesday
Local time
7:09 PM
EDT
Current temp
52°F
Unavailable
Live forecast
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
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
20 degrees cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
1h 45m on the road
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
Frequently Asked Questions
The drive from Windsor, VA to Chesapeake, VA covers 83.1 miles and takes about 1h 45m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Rasmussen Drive, Stockholm Drive, White Oak Road. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 41.6 miles from Windsor, VA. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $13.00 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.
The drive from Windsor, VA to Chesapeake, VA is easy. At 1h 45m with 0% highway, most drivers will find it relaxed and low-stress.
This route does not have any notably tricky sections. Most of the drive from Windsor, VA to Chesapeake, VA is straightforward, with well-signed roads and simple exits.
The route from Windsor, VA to Chesapeake, VA does not surface many named destination signs beyond the main corridor.
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