How far is Chesapeake, VA from Castlewood, VA?
The driving distance from Chesapeake, VA to Castlewood, VA is about 432 miles (695.2 km), with a travel time of about 08h 20m by car.
- The straight-line flight distance is about 331.9 miles (534.2 km).
- For a round trip, plan for roughly 16h 41m 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 08h 20m.
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 in Virginia
Route Weather Snapshot
Check the forecast at both ends before you head out.
Slight Chance Rain Showers
Sunny
Driving Route Map
The map below follows the saved road route between Chesapeake and Castlewood.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake and Castlewood.
-
1
Start on D Street
126 m · 21 sec · D Street
-
2
At the end of the road, turn right onto Poindexter Street
1617 ft · 29 sec · Poindexter Street
-
3
Take the ramp straight toward I 464 North
1284 ft · 18 sec
-
4
Merge slight left
1.2 mi · 1 min
-
5
Keep slight left to continue on I 264 East: Waterside Drive, Saint Paul Boulevard, Downtown, Norfolk
1.1 km · 1 min
-
6
Keep slight left to continue on Waterside Drive, St Paul's Boulevard
1095 ft · 27 sec
-
7
Keep slight left to continue on Saint Paul's Boulevard
1575 ft · 53 sec
-
8
Turn right onto Saint Pauls Boulevard
3199 ft · 1 min · Saint Pauls Boulevard
-
9
Continue on Monticello Avenue
1.2 mi · 2 min · Monticello Avenue
-
10
Turn left onto Church Street
148 m · 14 sec · Church Street
-
11
Continue on Granby Street
4 mi · 9 min · Granby Street
-
12
Turn left onto I 64
1001 ft · 26 sec
-
13
Merge slight left onto Hampton Roads Beltway
3.8 mi · 5 min · Hampton Roads Beltway
-
14
Continue on Hampton Roads Bridge-Tunnel
3.5 mi · 5 min · Hampton Roads Bridge-Tunnel
-
15
Continue on Hampton Roads Beltway
5.9 mi · 8 min · Hampton Roads Beltway
-
16
Keep slight left
61.1 mi · 1 hr 8 min
-
17
Take the exit slight right toward I 295, US 60: Washington, Rocky Mount NC
2434 ft · 32 sec
-
18
Keep slight right to continue on I 295 North: Washington
1.3 mi · 3 min
-
19
Merge slight left onto Korean War Veterans Memorial Highway
22.6 mi · 25 min · Korean War Veterans Memorial Highway
-
20
Keep slight right to continue on I 64 West: Charlottesville
2936 ft · 55 sec
-
21
Merge slight left onto I 64 West: Charlottesville
120.3 mi · 2 hr 11 min
-
22
Keep slight left
117.1 mi · 2 hr 10 min
-
23
Continue straight
1.3 mi · 1 min
-
24
Keep slight left
55.8 mi · 1 hr
-
25
Take the exit slight right toward US 58 Alternate, VA 75: Abingdon, South Holston Dam
890 ft · 25 sec
-
26
Turn right onto Cummings Street
1.3 km · 2 min · Cummings Street
-
27
At the end of the road, turn left onto Valley Street Northwest
1323 ft · 49 sec · Valley Street Northwest
-
28
At the end of the road, turn right onto Russell Road Northwest
1.5 km · 2 min · Russell Road Northwest
-
29
Turn slight right onto Porterfield Highway
10.3 mi · 15 min · Porterfield Highway
-
30
Continue on US 19
1.9 mi · 3 min · US 19
-
31
Turn left onto US Highway 58
12.4 mi · 17 min · US Highway 58
-
32
Turn right onto Memorial Drive
1.5 mi · 4 min · Memorial Drive
-
33
Turn left onto Trout Farm Road
825 ft · 23 sec · Trout Farm Road
-
34
Continue on Red Oak Ridge Road
1.3 km · 2 min · Red Oak Ridge Road
-
35
Turn slight right onto Church Street
61 m · 9 sec · Church Street
-
36
Arrive at your destination
0 m · 1 sec · Church Street
Car Route Details
A richer read on the saved driving route between Chesapeake and Castlewood.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
I 64 West
Merge slight left onto I 64 West: Charlottesville
120 mi · 02h 11m
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.
Slight Chance Rain Showers leaving Chesapeake and Sunny near Castlewood.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chesapeake to Castlewood?
The road trip is about 432 miles (695.2 km) and usually takes 08h 20m 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?
Craigsville is a useful midpoint, sitting about 215.4 miles from Chesapeake and 216.6 miles from Castlewood.
How much longer is the road route than the straight-line distance?
The direct path is about 331.9 miles (534.2 km), while the road route adds roughly 100.1 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 $59.70 one way or $119.39 round trip. Estimated CO2 is about 135.4 kg one way.
What should you check before leaving?
Before you leave, expect Slight Chance Rain Showers around Chesapeake and Sunny near Castlewood.
Stop Ideas Near Craigsville
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 Craigsville.
Staunton station
Clifton Forge
Kemper Street station
Charlottesville Union Station
Flight Path Map
This map shows the direct air route between Chesapeake and Castlewood. Straight-line distance: 331.96 mi (534.23 km).
#1 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
#2 Castlewood
Castlewood is a place in Virginia, United States.
| Population | 0 |
| Coordinates | 36.8901000, -82.2795900 |
| Altitude | 492 |
| Country | United States |
End: Castlewood (-82.27959, 36.8901)
Estimated Travel Time
Distance: 695 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 14h 23m |
| 40 mph (64.37 km/h) | 10h 48m |
| 50 mph (80.47 km/h) | 08h 38m |
| 60 mph (96.56 km/h) | 07h 11m |
| 70 mph (112.65 km/h) | 06h 10m |
| 80 mph (129 km/h) | 05h 23m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.92 | $59.70 | $119.39 |
| Mid-grade | $4.41 | $67.27 | $134.54 |
| Premium | $4.82 | $73.47 | $146.94 |
| Diesel | $6.20 | $94.43 | $188.85 |
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 06, 2026