How far is Woodlawn, VA from Chesapeake, VA?
The driving distance from Woodlawn, VA to Chesapeake, VA is about 295.3 miles (475.3 km), with a travel time of about 05h 15m by car.
- The straight-line flight distance is about 251.8 miles (405.2 km).
- For a round trip, plan for roughly 10h 30m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 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 05h 15m.
An early departure helps you fit a real stop into the day without turning the return into a late-night drive.
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.
Sunny
Driving Route Map
The map below follows the saved road route between Woodlawn and Chesapeake.
Turn-by-Turn Driving Directions
Step-by-step road directions between Woodlawn and Chesapeake.
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1
Start on Coulson Church Road
1031 ft · 25 sec · Coulson Church Road
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2
Turn left onto Carrollton Pike
3.3 mi · 5 min · Carrollton Pike
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3
Take the exit slight right toward I 77 South: Charlotte
1571 ft · 38 sec
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4
Merge slight left
5.7 mi · 7 min
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5
Take the exit slight right toward VA 148, SR 775: Fancy Gap
1381 ft · 36 sec
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6
Turn straight onto Chance Creek Road
1.4 km · 1 min · Chance Creek Road
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7
At the end of the road, turn right onto Fancy Gap Highway
9.4 mi · 11 min · Fancy Gap Highway
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8
Continue on North Andy Griffith Parkway
31.6 mi · 36 min · North Andy Griffith Parkway
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9
Keep slight left to continue on NC 74 East
13.3 mi · 16 min
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10
Keep slight left to continue on US 421 South: Greensboro
1.1 mi · 2 min
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11
Merge slight left onto Salem Parkway
11.4 mi · 13 min · Salem Parkway
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12
Keep slight right to continue on I 40 East: Greensboro, Martinsville
7.8 mi · 10 min
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13
Merge slight right
1.8 mi · 2 min
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14
Keep slight left
36.8 mi · 43 min
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15
Keep slight left to continue on I 85 North: Durham
9.4 mi · 11 min
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16
Keep slight left
1.8 mi · 2 min
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17
Continue straight
4.3 mi · 5 min
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18
Keep slight left
37.1 mi · 40 min
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19
Turn straight
4.9 mi · 5 min
-
20
Take the exit slight right toward US 1, US 158: Norlina
1002 ft · 32 sec
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21
Turn left
8.6 mi · 11 min
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22
Turn right
1.2 mi · 1 min
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23
Continue straight
5 mi · 6 min
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24
At the end of the road, turn left
28 mi · 33 min
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25
Take the exit left
955 ft · 23 sec
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26
Merge slight left onto Congressman G K Butterfield Highway
19.3 mi · 21 min · Congressman G K Butterfield Highway
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27
Take the exit slight right toward US 58 East: Emporia, Norfolk
683 ft · 17 sec
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28
Keep slight left to continue on US 58 East: Norfolk, Virginia Beach
735 ft · 18 sec
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29
Merge slight left
68.1 mi · 1 hr 29 min
-
30
Take the exit slight right toward I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
1.2 km · 2 min
-
31
Keep slight left to continue on I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
2322 ft · 57 sec
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32
Merge slight left onto Hampton Roads Beltway
3026 ft · 43 sec · Hampton Roads Beltway
-
33
Take the exit slight left toward I 264 East: Portsmouth, Norfolk
1.2 km · 1 min
-
34
Continue straight
3.7 mi · 5 min
-
35
Take the exit slight right toward VA 164 West, US 17: Martin Luther King Jr Expressway, Norfolk, Frederick Boulevard
920 ft · 23 sec
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36
Keep slight right to continue on US 17: Frederick Boulevard
1070 ft · 28 sec
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37
Turn right onto Frederick Boulevard
1.2 mi · 2 min · Frederick Boulevard
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38
At the end of the road, turn left onto George Washington Highway
1964 ft · 50 sec · George Washington Highway
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39
Turn right onto Elm Avenue
1.3 km · 1 min · Elm Avenue
-
40
Continue on South Norfolk Jordan Bridge
1.1 mi · 2 min · South Norfolk Jordan Bridge
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41
Turn straight onto Poindexter Street
1.1 km · 1 min · Poindexter Street
-
42
Turn left onto D Street
126 m · 18 sec · D Street
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43
Arrive at your destination
0 m · 1 sec · D Street
Car Route Details
A richer read on the saved driving route between Woodlawn and Chesapeake.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
US 58 East
Merge slight left
68.1 mi · 01h 29m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A longer out-and-back drive
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
Sunny leaving Woodlawn and Sunny near Chesapeake.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Woodlawn to Chesapeake?
The road trip is about 295.3 miles (475.3 km) and usually takes 05h 15m in normal driving conditions.
Is this a same-day trip or an overnight route?
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
What is the halfway point on this route?
Virgilina is a useful midpoint, sitting about 161.2 miles from Woodlawn and 134.2 miles from Chesapeake.
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 43.5 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 8:00 AM EST. If you want a more comfortable same-day return, try to leave by 6:30 AM EST.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $40.23 one way or $80.46 round trip. Estimated CO2 is about 92.6 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Woodlawn and Sunny near Chesapeake.
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 Woodlawn and Chesapeake. Straight-line distance: 251.77 mi (405.19 km).
#1 Woodlawn
Woodlawn is a place in Virginia, United States.
| Population | 0 |
| Coordinates | 36.7223500, -80.8228500 |
| Altitude | 768 |
| Country | United States |
#2 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
End: D Street (-76.275044, 36.81897)
Estimated Travel Time
Distance: 475 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 09h 50m |
| 40 mph (64.37 km/h) | 07h 23m |
| 50 mph (80.47 km/h) | 05h 54m |
| 60 mph (96.56 km/h) | 04h 55m |
| 70 mph (112.65 km/h) | 04h 13m |
| 80 mph (129 km/h) | 03h 41m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.86 | $40.23 | $80.46 |
| Mid-grade | $4.35 | $45.34 | $90.67 |
| Premium | $4.77 | $49.69 | $99.39 |
| Diesel | $6.16 | $64.16 | $128.31 |
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