Chesapeake, VA to Woodlawn, VA is 323.7 miles and takes about 6h 30m via I 85 and Portsmouth Boulevard, with a fuel budget near $51 and enough daylight to finish in a day. This trip stays within the Southeast region, entirely within Virginia, offering a straightforward drive. You'll find it's a highway-focused route, making it a good option if you prefer covering ground efficiently. With a recommended one-day duration, it’s manageable for a single stretch of driving without needing an overnight stay.
Trip Pace
Same-day drive is realistic
A same-day return is possible, but it will make for a full day on the road.
Break Rhythm
1 planned break
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
161.8 miles from Chesapeake, VA
A natural place for your longest stop of the day
, about 3h 21m into the drive
.
Main Roads
Road
Distance
Duration
I 85
88.4 mi
1h 39m
Portsmouth Boulevard
62.1 mi
1h 21m
Julian R Allsbrook Highway
24.9 mi
29m
John Gold Memorial Expressway
20.9 mi
23m
I 40
20.3 mi
24m
I 95
19.5 mi
20m
Winston-Salem Northern Beltway
11.1 mi
12m
South Andy Griffith Parkway
10.7 mi
12m
Longest stretch:
I 85
— 88.4 mi, about 1h 39m
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake, VA and Woodlawn, VA.
1
Start on D Street
412 ft·20 sec·D Street
2
At end of road, turn right onto US 460; VA 166
0.3 mi·29 sec·Poindexter Street
3
Take the ramp
0.2 mi·18 sec
Toward I 464 North
4
Merge onto I 464
1.2 mi·1 min·I 464
5
Keep slight right at fork
0.1 mi·14 sec
Exit 6AToward I 264 West Toll: Downtown Tunnel, PortsmouthUse the slight right lane.
6
Keep slight left at fork
0.5 mi·1 min
Toward I 264 West Toll: TunnelUse the slight left / slight right lanes.
7
Merge onto I 264; US 460 ALT
6.7 mi·9 min·I 264; US 460 ALT
Use the straight / slight right lanes.
8
Keep slight right at fork
0.6 mi·47 sec
Toward I 664: Bowers Hill, Suffolk, RichmondUse the slight right lane.
9
Merge onto I 664
0.4 mi·31 sec·Hampton Roads Beltway
10
Take the exit
0.3 mi·54 sec
Exit 13A-BToward US 13, US 58, US 460, VA 191 North: Suffolk, Military HighwayUse the slight right lane.
11
Keep slight left at fork
0.6 mi·1 min
12
Continue on US 13; US 58; US 460
2.4 mi·3 min·West Military Highway
13
Continue on US 13; US 58; US 460
62 mi·1 hr 21 min·Portsmouth Boulevard
Use the straight / right lanes.
14
Continue on US 58
4.5 mi·5 min·Courtland Road
15
Take the exit
0.2 mi·22 sec
Toward I 95 South: Rocky Mt N.C.
16
Merge onto I 95
19 mi·20 min·I 95
17
Take the exit
0.2 mi·26 sec
Toward US 158: Roanoke Rapids, Murfreesboro, Weldon
18
Turn right onto US 158
0.8 mi·1 min·Julian R Allsbrook Highway
19
Turn straight onto US 158
2.9 mi·3 min·East Littleton Road
20
Continue on US 158
24 mi·28 min·Julian R Allsbrook Highway
21
Continue on US 158 Bypass
5.1 mi·5 min·US 158 Bypass
22
Continue on US 158; US 401
1.2 mi·1 min·US 158; US 401
23
At end of road, turn left onto US 1; US 158
8.7 mi·10 min·US 1; US 158
24
Turn right onto Flemingtown Road
0.2 mi·11 sec·Flemingtown Road
25
Take the exit
0.2 mi·28 sec
26
Merge onto I 85
1.9 mi·2 min·I 85
27
Keep slight right at fork onto I 85
44 mi·48 min·I 85
Use the straight / slight right lanes.
28
Keep slight left at fork onto I 85; US 70
42 mi·48 min·I 85; US 70
Use the straight / slight right lanes.
29
Keep slight right at fork onto I 40
7.7 mi·9 min·I 40
Use the straight / slight left lanes.
30
Keep slight right at fork onto I 40; US 220
13 mi·15 min·I 40; US 220
Use the straight lane.
31
Keep slight right at fork onto US 421
6.5 mi·7 min·Salem Parkway
Exit 206Toward US 421 North: KernersvilleUse the straight lane.
32
Take the exit
0.8 mi·1 min
Exit 227Toward NC 74 WestUse the straight / slight right lanes.
33
Continue on NC 74
11 mi·12 min·Winston-Salem Northern Beltway
Use the straight / slight right lanes.
34
Keep slight left at fork onto NC 74
1.8 mi·2 min·NC 74
Toward US 52 North: Mount AiryUse the straight / slight right lanes.
35
Merge onto US 52
21 mi·23 min·John Gold Memorial Expressway
Use the straight lane.
36
Keep slight right at fork onto US 52
11 mi·12 min·South Andy Griffith Parkway
37
Continue on US 52
9.4 mi·10 min·Fancy Gap Highway
38
Turn left onto VA 148
0.7 mi·48 sec·VA 148
39
Take the exit
0.2 mi·30 sec
40
Merge onto I 77
5.7 mi·6 min·I 77
41
Take the exit
0.2 mi·33 sec
Exit 14Toward US 58, US 221: Hillsville, Galax
42
Turn left onto US 58; US 221
3.4 mi·5 min·Carrollton Pike
Use the straight lane.
43
Turn right onto SR 620
0.2 mi·25 sec·Coulson Church Road
44
Arrive at destination
SR 620
Trip Plan
Given the 6-hour 30-minute duration, starting early in the morning from Chesapeake is advisable to ensure you reach Woodlawn with daylight to spare. With only one recommended stop, plan it strategically along I 85 for fuel and a quick break, perhaps around the halfway point. The longest stretch without a major change in road type is 88.4 miles, so be prepared for that segment. Keep an eye on your fuel gauge, especially before entering longer stretches of I 85, as services can sometimes be spaced out on interstates.
Morning Departure
Start early — leave by 6-7 AM to arrive at a reasonable hour.
Evening Departure
This is a long drive — plan for a morning departure or consider splitting it into two days.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 161.8 miles from Chesapeake, VA, or about 3h 21m into the drive.
The longest continuous stretch on this route runs about 88.4 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 71 miles or 1h 35m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 161.8 miles or 3h 21m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 5h 22m
Traffic, exits, and arrival timing usually matter more near Woodlawn, VA than in the middle of the route.
Before You Leave
+
Open the route before leaving Chesapeake, 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 Chesapeake, VA
This is one driving day of about 323.7 miles and 6h 30m.
Your first comfortable stop window is around 71 miles from Chesapeake, VA.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 1 real break rather than only quick fuel stops.
The longest stretch is on I 85 for about 88.4 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 33
5 decision points cluster between mile 1.8 and 251.8 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
9
1.8 mi into trip|~2m in
Keep slight right at fork toward I 264 West Toll: Downtown Tunnel, Portsmouth
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 6A
Toward I 264 West Toll: Downtown Tunnel, Portsm...
7
1.9 mi into trip|~2m in
Keep slight left at fork toward I 264 West Toll: Tunnel
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / slight right lanes.
Toward I 264 West Toll: Tunnel
8
9.2 mi into trip|~13m in
Keep slight right at fork toward I 664: Bowers Hill, Suffolk, Richmond
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Toward I 664: Bowers Hill, Suffolk, Richmond
8
10.2 mi into trip|~15m in
Take the exit toward US 13, US 58, US 460, VA 191 North: Suffolk, Military Highway
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 13A-B
Toward US 13, US 58, US 460, VA 191 North: Suff...
8
251.8 mi into trip|~5h 5m in|US 421 / Salem Parkway
Keep slight right at fork onto US 421 / Salem Parkway toward US 421 North: Kernersville
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight lane.
Exit 206
Toward US 421 North: Kernersville
Fuel & Cost
Regular Gas
$50.62 one way
$101.24 round trip
$3.97/gal25.4 MPG avg113 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.34
$55.35
$110.70
premium
$4.70
$59.91
$119.82
diesel
$5.61
$71.47
$142.94
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$51
Meals
$25–$50
Total
$76–$101
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 113.3 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $34 in charging
· 1 stop
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
97.1
1
$33.99
$15.54
Efficient EV
80.9
0
$28.32
$12.95
EV Truck/SUV
129.5
1
$45.32
$20.72
Gas CO2
113 kg
EV CO2
38 kg (66% less)
Plan for 1 charging stop. A 30-minute DC fast charge mid-route should be enough to complete the trip comfortably.
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 16, 2026
Origin
Chesapeake, VA
Morning
in Chesapeake on Sunday
Local time
6:21 AM
EDT
Current temp
93°F
Mostly Sunny
SW 14 mph0% chanceLive forecast
Special Weather Statement
Special Weather Statement issued April 16 at 1:12PM EDT by NWS Wakefield VA
Red Flag Warning
Red Flag Warning issued April 16 at 9:43AM EDT until April 16 at 7:00PM EDT by NWS Baltimore MD/Washington DC
Destination
Woodlawn, VA
Morning
in Woodlawn on Sunday
Local time
6:21 AM
EDT
Current temp
46°F
Unavailable
Live forecast
56°F
Henderson, NC
162 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
47 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
6h 30m on the road
Start early — leave by 6-7 AM to arrive at a reasonable hour.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
National Parks Near This Route
Worth a detour if your schedule allows.
Fort Monroe National Monument
National Monument
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...
14 mi from route
~34 min detour
Free
Park Closure: Road Closure and Fishing Pier Impact
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This drive is primarily a highway-focused experience, with 61% of the journey on major roadways like I 85. Expect stretches where you'll be cruising at highway speeds for extended periods, including one segment of 88.4 miles solely on I 85. While Portsmouth Boulevard and Julian R Allsbrook Highway will offer a change of pace, the overall character leans towards efficient travel rather than winding country roads. You'll likely find the route progresses smoothly, allowing for consistent progress towards your destination.
61% highway — fuel and pacing are the main things to plan.
44 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 88.4 mi on I 85.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on I 85 and Portsmouth Boulevard. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 1.8 miles in.
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 33 significant decision points across 323.7 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 1.8 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 1.9 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 9.2 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Chesapeake, VA and Woodlawn, VA, road signs point toward Murfreesboro and Weldon.
Chesapeake is a town of 245,000 people (2019) in the Hampton Roads region of Eastern Virginia. Chesapeake is a diverse city in which a few urban areas are located; it also has many square miles of protected farmland, forests, and wetlands, including a substantial portion of the Great Dismal Swamp National Wildlife Refuge.
Doable as a same-day drive at 6h 30m. Total distance: 323.7 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
6h 30m drive, plan rest stops for pacing.
Frequently Asked Questions
The longest stretch is about 88.4 miles on I 85. The full list of main roads is in the Roads section above.
Yes — we found about 23 rest areas or service plazas within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Woodlawn, VA before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 1 meaningful breaks. There are 23 rest areas along the route for bathroom stops.
The main spots that need attention: at 1.8 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 1.9 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 9.2 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — Fort Monroe National Monument. See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 6.5 hours each way, a round trip means 13.0 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Woodlawn, VA before the return drive.
