This 105.6-mile drive from Woodlake to Chesapeake, Virginia, is best tackled in a single day, taking approximately 2 hours and 25 minutes. Expect a fuel cost of around $17 for this trip. The route primarily utilizes James River Drive, Colonial Trail West, and World War II Veterans Memorial Highway, offering a local driving experience with frequent turns rather than long stretches of highway. Given its manageable distance and duration, it's an ideal day trip, allowing for flexibility in your schedule. You'll be traveling within the Southeast region of Virginia for the entire journey.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
52.8 miles from Woodlake, VA
A natural place for your longest stop of the day
, about 1h 12m into the drive
.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 2h 25m. Total distance: 105.6 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
2h 25m drive, comfortable solo distance.
Scenic Drive
Turn-heavy local drive route profile with national parks nearby.
Drive Character
You'll find this drive to be quite 'turn-heavy,' indicating a more local and less highway-dominated experience. With only about 11% of the journey on highways, expect a dynamic route that winds through various local roads. The longest uninterrupted stretch you'll encounter is 14.6 miles on James River Drive. This profile suggests a journey where you'll be actively navigating, with frequent changes in direction and speed, rather than a monotonous interstate cruise.
This route has more turning and local-road decision points than a simple highway run.
There are about 32 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
James River Drive is the longest continuous segment at about 14.6 miles.
How Hard Is This Drive?
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 4.5 miles in near SR 754 / Commonwealth Centre Parkway.
Driving Effort10/10
High effort - long or complex enough to need steady focus all day
Balances navigation complexity with total wheel time.
This is a demanding drive. With 20 significant decision points across 105.6 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 4.5 miles (SR 754 / Commonwealth Centre Parkway): Lane positioning matters here; at 5.4 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 17.9 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Critical Maneuvers
5 of 20 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
6
4.5 mi into trip|~9m in|SR 754 / Commonwealth Centre Parkway
Turn right onto SR 754 / Commonwealth Centre Parkway
Lane positioning matters here
Use the right lane.
8
5.4 mi into trip|~10m in
Keep slight right at fork toward VA 288 South
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Toward VA 288 South
7
17.9 mi into trip|~25m in
Keep slight right at fork toward I 95 South: Petersburg
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Toward I 95 South: Petersburg
7
19.6 mi into trip|~28m in
Take the exit toward VA 10 East: Hopewell
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the right lane.
Exit 61A
Toward VA 10 East: Hopewell
6
92 mi into trip|~2h 4m in|VA 164 / Western Freeway
Keep slight right at fork onto VA 164 / Western Freeway
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Main Roads
Road
Distance
Duration
James River Drive
14.6 mi
19m
Colonial Trail West
13.3 mi
15m
World War II Veterans Memorial Highway
12.1 mi
14m
Old Stage Highway
12 mi
15m
Colonial Trail East
9.8 mi
11m
Western Freeway
7.4 mi
9m
West Hundred Road
6.8 mi
10m
Bridge Road
6.2 mi
10m
Longest stretch:
James River Drive
— 14.6 mi, about 19m
Turn-by-Turn Driving Directions
Step-by-step road directions between Woodlake, VA and Chesapeake, VA.
1
Start on this road
344 ft·29 sec·this road
2
At end of road, turn left onto SR 3600
0.8 mi·1 min·Woodlake Village Parkway
3
Continue on SR 3600
0.7 mi·1 min·Woodlake Village Parkway
4
At end of road, turn left onto US 360
2.9 mi·5 min·Hull Street Road
Use the left lane.
5
Turn right onto SR 754
0.9 mi·1 min·Commonwealth Centre Parkway
Use the right lane.
6
Take the ramp
62 ft·1 sec
7
Keep slight right at fork
0.3 mi·40 sec
Toward VA 288 SouthUse the slight right lane.
8
Merge onto VA 288
12 mi·14 min·World War II Veterans Memorial Highway
9
Keep slight right at fork
0.3 mi·37 sec
Toward I 95 South: PetersburgUse the slight right lane.
10
Merge onto I 95
1.5 mi·1 min·Richmond-Petersburg Turnpike
11
Take the exit
0.3 mi·38 sec
Exit 61AToward VA 10 East: HopewellUse the right lane.
12
Continue on VA 10
6.8 mi·10 min·West Hundred Road
Use the left / uturn lanes.
13
Continue on VA 10
2.9 mi·4 min·West Randolph Road
14
Continue on VA 10; VA 156 BUS
15 mi·19 min·James River Drive
15
Continue on VA 10
13 mi·15 min·Colonial Trail West
16
At end of road, turn left onto VA 10; VA 31
1.0 mi·1 min·Rolfe Highway
17
Take the exit
149 ft·6 sec
18
Merge onto VA 10
9.8 mi·11 min·Colonial Trail East
19
Continue on VA 10
12 mi·15 min·Old Stage Highway
Use the left lane.
20
Keep slight left at fork onto US 258
2.8 mi·3 min·Brewers Neck Boulevard
21
Take the exit
0.1 mi·19 sec
22
Merge onto US 17
2.3 mi·3 min·Carrollton Boulevard
23
Continue on US 17
6.2 mi·10 min·Bridge Road
Use the left lane.
24
Keep slight right at fork onto VA 164
7.4 mi·9 min·Western Freeway
Use the slight right lane.
25
Merge onto US 58; VA 164
0.7 mi·46 sec·Martin Luther King Freeway
26
Take the exit
0.3 mi·35 sec
Toward VA 141 South: Downtown PortsmouthUse the right lane.
27
Turn straight onto US 58
0.9 mi·1 min·London Boulevard
28
Turn right onto Elm Avenue
2.4 mi·4 min·Elm Avenue
Use the straight / left / right lanes.
29
Continue on VA 337
1.1 mi·2 min·South Norfolk Jordan Bridge
30
Turn straight onto VA 337
0.7 mi·1 min·Poindexter Street
Use the straight lane.
31
Turn left onto D Street
412 ft·18 sec·D Street
32
Arrive at destination
D Street
Trip Plan
For this 105.6-mile trip, consider leaving in the morning to fully enjoy the day, as it's easily completed within a few hours. Since there are no specific stops suggested, you have the flexibility to pause whenever you need a break or want to stretch your legs. Keep an eye on your navigation, as the 'turn-heavy' nature of the route means paying attention to upcoming turns is key. With a fuel cost estimated at $17, it's a budget-friendly excursion, so you won't need to worry excessively about frequent refueling stops.
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 52.8 miles from Woodlake, VA, or about 1h 12m into the drive.
The longest continuous stretch on this route runs about 14.6 miles.
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 23 miles or 33m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 52.8 miles or 1h 12m 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 55m
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 Woodlake, 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 Woodlake, VA
This is one driving day of about 105.6 miles and 2h 25m.
Your first comfortable stop window is around 23 miles from Woodlake, VA.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on James River Drive for about 14.6 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 52.8 mi from Woodlake, VA
· 1h 12m into the drive
Place data sourced from public business listings. Hours and availability may vary.
National Parks Near This Route
Worth a detour if your schedule allows.
Colonial National Historical Park
National Historical Park
On May 13, 1607, Jamestown was established as the first permanent English settlement in North America. Three cultures came together – European, Virginia Indian and African–to create a new society that...
11 mi from route
~27 min detour
$15
near mile 65.5
Park Closure: Rehabilitation of Colonial Parkway Continues
Fort Monroe's story spans from prehistory to the 2000s. Kecoughtan Indians occupied Old Point Comfort before the arrival of English colonists. The first enslaved Africans arrived in 1619. Those escapi...
11 mi from route
~29 min detour
Free
near mile 98.3
Two hundred ninety-two days, eight offensives, over 70,000 casualties, U. S. Colored Troops, and the decline of Gen. Lee's Army of Northern Virginia all describe the Siege of Petersburg. U.S. forces c...
12 mi from route
~31 min detour
Free
near mile 21.8
Park data from the National Park Service API. Alerts update every 2 hours.
Fuel & Cost
Regular Gas
$16.51 one way
$33.03 round trip
$3.97/gal25.4 MPG avg37 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.34
$18.06
$36.11
premium
$4.70
$19.54
$39.09
diesel
$5.61
$23.32
$46.63
Estimated Tolls: $0.10
Richmond-Petersburg Turnpike
(1.5 mi)$0.10
Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.
Estimated Trip Cost (one way, 1 person)
Fuel
$17
Tolls
$0
Meals
$25–$50
Total
$42–$67
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 36.9 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $11 in charging
· 0 stops
· 68% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
31.7
0
$11.09
$5.07
Efficient EV
26.4
0
$9.24
$4.22
EV Truck/SUV
42.2
0
$14.78
$6.76
Gas CO2
37 kg
EV CO2
12 kg (68% 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.
Forecast as of Apr 12, 2026
Origin
Woodlake, VA
Late night
in Woodlake on Friday
Local time
1:41 AM
EDT
Current temp
64°F
Unavailable
Live forecast
Destination
Chesapeake, VA
Late night
in Chesapeake on Friday
Local time
1:41 AM
EDT
Current temp
52°F
Unavailable
Live forecast
52°F
Waverly, VA
53 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
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
12 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
2h 25m 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 Woodlake, VA to Chesapeake, VA covers 105.6 miles and takes about 2h 25m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are James River Drive, Colonial Trail West, World War II Veterans Memorial Highway. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 52.8 miles from Woodlake, VA. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $16.51 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.
This is a demanding drive. With 20 significant decision points across 105.6 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
The main spots that need attention: at 4.5 miles (SR 754 / Commonwealth Centre Parkway): Lane positioning matters here; at 5.4 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 17.9 miles: Highway fork - watch signs carefully. Lane positioning matters here.
The route from Woodlake, VA to Chesapeake, VA does not surface many named destination signs beyond the main corridor.
Yes. Nearby national parks include Colonial National Historical Park, Fort Monroe National Monument and Petersburg National Battlefield.
