How far is Chesapeake, VA from Woodstock, VA?
The driving distance from Chesapeake, VA to Woodstock, VA is about 238 miles (383 km), with a travel time of about 04h 56m by car.
- The straight-line flight distance is about 187.4 miles (301.6 km).
- For a round trip, plan for roughly 09h 52m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 AM EDT.
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 04h 56m.
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.
City in Virginia
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny then Slight Chance Rain Showers
Chance Rain Showers
Driving Route Map
The map below follows the saved road route between Chesapeake and Woodstock.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake and Woodstock.
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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 left to continue on I 264 East: Waterside Drive, Saint Paul Boulevard, Downtown, Norfolk
1.1 km · 1 min
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6
Keep slight left to continue on Waterside Drive, St Paul's Boulevard
1095 ft · 27 sec
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7
Keep slight left to continue on Saint Paul's Boulevard
1575 ft · 53 sec
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8
Turn right onto Saint Pauls Boulevard
3199 ft · 1 min · Saint Pauls Boulevard
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9
Continue on Monticello Avenue
1.2 mi · 2 min · Monticello Avenue
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10
Turn left onto Church Street
148 m · 14 sec · Church Street
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11
Continue on Granby Street
4 mi · 9 min · Granby Street
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12
Turn left onto I 64
1001 ft · 26 sec
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13
Merge slight left onto Hampton Roads Beltway
3.8 mi · 5 min · Hampton Roads Beltway
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14
Continue on Hampton Roads Bridge-Tunnel
3.5 mi · 5 min · Hampton Roads Bridge-Tunnel
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15
Continue on Hampton Roads Beltway
5.9 mi · 8 min · Hampton Roads Beltway
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16
Keep slight left
61.1 mi · 1 hr 8 min
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17
Take the exit slight right toward I 295, US 60: Washington, Rocky Mount NC
2434 ft · 32 sec
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18
Keep slight right to continue on I 295 North: Washington
1.3 mi · 3 min
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19
Merge slight left onto Korean War Veterans Memorial Highway
11.9 mi · 13 min · Korean War Veterans Memorial Highway
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20
Take the exit slight left toward I 95 North: Washington
2.4 mi · 3 min
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21
Merge slight right
45.7 mi · 50 min
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22
Keep slight right
1.6 mi · 2 min
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23
Keep slight right to continue on US 17 Business: Falmouth
1635 ft · 42 sec
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24
Turn left onto Warrenton Road
22.9 mi · 33 min · Warrenton Road
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25
Continue on Marsh Road
4.2 mi · 7 min · Marsh Road
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26
Turn right onto James Madison Highway
4.6 mi · 6 min · James Madison Highway
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27
Continue on Eastern Bypass
2.4 mi · 3 min · Eastern Bypass
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28
Keep slight right to continue on Eastern Bypass
2.3 mi · 3 min · Eastern Bypass
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29
Continue on James Madison Highway
6.7 mi · 9 min · James Madison Highway
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30
Continue on Winchester Road
2.7 mi · 4 min · Winchester Road
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31
Turn left
18.6 mi · 20 min
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32
Continue straight
9.6 mi · 10 min
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33
Keep slight left to continue on I 81 South: Roanoke
1 km · 1 min
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34
Merge slight right onto I 81 South: Roanoke
8.5 mi · 9 min
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35
Take the exit slight right toward SR 651: Toms Brook
1775 ft · 44 sec
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36
Turn left onto Mount Olive Road
1.5 km · 2 min · Mount Olive Road
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37
At the end of the road, turn right onto Old Valley Pike
2384 ft · 51 sec · Old Valley Pike
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38
Continue on Main Street
1.2 km · 1 min · Main Street
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39
Continue on Old Valley Pike
4.4 mi · 6 min · Old Valley Pike
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40
Continue on North Main Street
1 mi · 3 min · North Main Street
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41
Turn right onto West Court Street
35 m · 5 sec · West Court Street
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42
Arrive at your destination
0 m · 1 sec · West Court Street
Car Route Details
A richer read on the saved driving route between Chesapeake and Woodstock.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
Hampton Roads Beltway
Keep slight left
61.1 mi · 01h 08m
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.
Mostly Sunny then Slight Chance Rain Showers leaving Chesapeake and Chance Rain Showers near Woodstock.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chesapeake to Woodstock?
The road trip is about 238 miles (383 km) and usually takes 04h 56m 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?
Bowling Green is a useful midpoint, sitting about 119 miles from Chesapeake and 119 miles from Woodstock.
How much longer is the road route than the straight-line distance?
The direct path is about 187.4 miles (301.6 km), while the road route adds roughly 50.6 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 EDT. If you want a more comfortable same-day return, try to leave by 7:08 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $33.27 one way or $66.54 round trip. Estimated CO2 is about 74.7 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny then Slight Chance Rain Showers around Chesapeake and Chance Rain Showers near Woodstock.
Stop Ideas Near Bowling Green
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 Bowling Green.
Fredericksburg
Ashland
Richmond Staples Mill Road station
Quantico
Flight Path Map
This map shows the direct air route between Chesapeake and Woodstock. Straight-line distance: 187.41 mi (301.6 km).
#1 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
#2 Woodstock
Town in Shenandoah County, Virginia, United States
| Population | 5,248 |
| Coordinates | 38.8817800, -78.5058400 |
| Altitude | 239 |
| Country | United States |
End: Woodstock (-78.50584, 38.88178)
Estimated Travel Time
Distance: 383 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 07h 55m |
| 40 mph (64.37 km/h) | 05h 57m |
| 50 mph (80.47 km/h) | 04h 45m |
| 60 mph (96.56 km/h) | 03h 57m |
| 70 mph (112.65 km/h) | 03h 24m |
| 80 mph (129 km/h) | 02h 58m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $33.27 | $66.54 |
| Mid-grade | $4.43 | $37.20 | $74.41 |
| Premium | $4.78 | $40.14 | $80.27 |
| Diesel | $5.62 | $47.24 | $94.48 |
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 · Apr 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.