How far is Chesapeake, VA from Woodlawn, VA?
The driving distance from Chesapeake, VA to Woodlawn, VA is about 323.7 miles (520.9 km), with a travel time of about 06h 30m by car.
- The straight-line flight distance is about 251.8 miles (405.2 km).
- For a round trip, plan for roughly 13h 01m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 7:30 AM EST.
Reverse, save, or send this route
This drive is better planned with a longer stop or an overnight stay. Copy the route link, send it to another device, or print a clean version before you head out.
This drive is better planned with a longer stop or an overnight stay.
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 06h 30m.
Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
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.
Town of the United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Driving Route Map
The map below follows the saved road route between Chesapeake and Woodlawn.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake and Woodlawn.
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1
Start on D Street
126 m · 21 sec · D Street
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2
At the end of the road, turn right onto Poindexter Street
1617 ft · 29 sec · Poindexter Street
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3
Take the ramp straight toward I 464 North
1284 ft · 18 sec
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4
Merge slight left
1.2 mi · 1 min
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5
Keep slight right to continue on I 264 West Toll: Downtown Tunnel, Portsmouth
580 ft · 14 sec
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6
Keep slight left to continue on I 264 West Toll: Tunnel
2569 ft · 1 min
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7
Merge slight left
6.7 mi · 10 min
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8
Keep slight right to continue on I 664: Bowers Hill, Suffolk, Richmond
1 km · 47 sec
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9
Merge slight left onto Hampton Roads Beltway
2197 ft · 31 sec · Hampton Roads Beltway
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10
Take the exit slight right toward US 13, US 58, US 460, VA 191 North: Suffolk, Military Highway
1598 ft · 54 sec
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11
Keep slight left
3155 ft · 1 min
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12
Continue on West Military Highway
2.4 mi · 3 min · West Military Highway
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13
Continue on Portsmouth Boulevard
62.1 mi · 1 hr 21 min · Portsmouth Boulevard
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14
Continue on Courtland Road
4.5 mi · 6 min · Courtland Road
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15
Take the exit slight right toward I 95 South: Rocky Mt N.C.
909 ft · 22 sec
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16
Merge slight left
19.5 mi · 21 min
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17
Take the exit slight right toward US 158: Roanoke Rapids, Murfreesboro, Weldon
901 ft · 27 sec
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18
Turn right onto Julian R Allsbrook Highway
1.2 km · 1 min · Julian R Allsbrook Highway
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19
Turn straight onto East Littleton Road
2.9 mi · 3 min · East Littleton Road
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20
Continue on Julian R Allsbrook Highway
24.2 mi · 28 min · Julian R Allsbrook Highway
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21
Continue straight
5.1 mi · 6 min
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22
Continue straight
1.2 mi · 1 min
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23
At the end of the road, turn left
8.7 mi · 11 min
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24
Turn right onto Flemingtown Road
821 ft · 11 sec · Flemingtown Road
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25
Take the exit slight right
1114 ft · 28 sec
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26
Merge slight left
1.9 mi · 2 min
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27
Keep slight right
44.1 mi · 49 min
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28
Keep slight left
42.3 mi · 49 min
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29
Keep slight right
7.7 mi · 9 min
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30
Keep slight right
12.6 mi · 15 min
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31
Keep slight right to continue on Salem Parkway
6.5 mi · 8 min · Salem Parkway
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32
Take the exit slight right toward NC 74 West
1.3 km · 2 min
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33
Continue on Winston-Salem Northern Beltway
11.1 mi · 13 min · Winston-Salem Northern Beltway
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34
Keep slight left to continue on US 52 North: Mount Airy
1.8 mi · 2 min
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35
Merge slight left onto John Gold Memorial Expressway
20.9 mi · 24 min · John Gold Memorial Expressway
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36
Keep slight right to continue on South Andy Griffith Parkway
10.7 mi · 13 min · South Andy Griffith Parkway
-
37
Continue on Fancy Gap Highway
9.4 mi · 11 min · Fancy Gap Highway
-
38
Turn left
1.1 km · 48 sec
-
39
Take the exit slight right
1276 ft · 31 sec
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40
Merge slight left
5.7 mi · 7 min
-
41
Take the exit slight right toward US 58, US 221: Hillsville, Galax
1286 ft · 33 sec
-
42
Turn left onto Carrollton Pike
3.4 mi · 5 min · Carrollton Pike
-
43
Turn right onto Coulson Church Road
1031 ft · 25 sec · Coulson Church Road
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44
Arrive at your destination
0 m · 1 sec · Coulson Church Road
Car Route Details
A richer read on the saved driving route between Chesapeake and Woodlawn.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
Portsmouth Boulevard
Continue on Portsmouth Boulevard
62.1 mi · 01h 21m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
Better with a longer stop
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
Sunny leaving Chesapeake and Sunny near Woodlawn.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chesapeake to Woodlawn?
The road trip is about 323.7 miles (520.9 km) and usually takes 06h 30m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
What is the halfway point on this route?
Virgilina is a useful midpoint, sitting about 161.6 miles from Chesapeake and 162.1 miles from Woodlawn.
How much longer is the road route than the straight-line distance?
The direct path is about 251.8 miles (405.2 km), while the road route adds roughly 71.9 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 6:00 AM to 7:30 AM EST. Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $44.09 one way or $88.19 round trip. Estimated CO2 is about 101.5 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Chesapeake and Sunny near Woodlawn.
Stop Ideas Near Virgilina
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Virgilina.
Danville
Durham
Burlington
Cary
Flight Path Map
This map shows the direct air route between Chesapeake and Woodlawn. Straight-line distance: 251.77 mi (405.19 km).
#1 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
#2 Woodlawn
Woodlawn is a place in Virginia, United States.
| Population | 0 |
| Coordinates | 36.7223500, -80.8228500 |
| Altitude | 768 |
| Country | United States |
End: Woodlawn (-80.82285, 36.72235)
Estimated Travel Time
Distance: 521 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 10h 47m |
| 40 mph (64.37 km/h) | 08h 05m |
| 50 mph (80.47 km/h) | 06h 28m |
| 60 mph (96.56 km/h) | 05h 23m |
| 70 mph (112.65 km/h) | 04h 37m |
| 80 mph (129 km/h) | 04h 02m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.86 | $44.09 | $88.19 |
| Mid-grade | $4.35 | $49.69 | $99.38 |
| Premium | $4.77 | $54.46 | $108.92 |
| Diesel | $6.16 | $70.31 | $140.63 |
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 · Nov 09, 2026