How far is Wise, VA from Chesapeake, VA?
The driving distance from Wise, VA to Chesapeake, VA is about 422.5 miles (679.9 km), with a travel time of about 07h 30m by car.
- The straight-line flight distance is about 348.3 miles (560.5 km).
- For a round trip, plan for roughly 15h 01m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 7:30 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 07h 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.
Independent city in Virginia, 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 Wise and Chesapeake.
Turn-by-Turn Driving Directions
Step-by-step road directions between Wise and Chesapeake.
-
1
Start on East Main Street
570 ft · 20 sec · East Main Street
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2
Turn left onto Park Avenue Northeast
1247 ft · 44 sec · Park Avenue Northeast
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3
Turn right onto Darden Drive Northeast
1 mi · 2 min · Darden Drive Northeast
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4
Continue on Coeburn Mountain Road
5.3 mi · 9 min · Coeburn Mountain Road
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5
Continue on Wise Mountain Road Northwest
1.5 km · 2 min · Wise Mountain Road Northwest
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6
At the end of the road, turn right onto Laurel Avenue
1324 ft · 36 sec · Laurel Avenue
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7
Turn sharp left onto Front Street East
1.1 km · 1 min · Front Street East
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8
Turn sharp right
949 ft · 24 sec
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9
Turn left onto US 58 Alternate East
871 ft · 24 sec
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10
Merge slight left onto Bull Run Road
11.2 mi · 16 min · Bull Run Road
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11
Continue on Trail of the Lonesome Pine
111 m · 7 sec · Trail of the Lonesome Pine
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12
Continue on US Highway 58 Alternate
6.9 mi · 10 min · US Highway 58 Alternate
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13
Continue on Trail of the Lonesome Pine
7.8 mi · 11 min · Trail of the Lonesome Pine
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14
Turn right
12.7 mi · 19 min
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15
Turn left onto West Main Street
2816 ft · 1 min · West Main Street
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16
Turn right onto Preston Street Southwest
1006 ft · 33 sec · Preston Street Southwest
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17
At the end of the road, turn left onto Bradley Street Southwest
2716 ft · 1 min · Bradley Street Southwest
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18
At the end of the road, turn right onto Cummings Street
1 km · 1 min · Cummings Street
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19
Take the exit slight right
1308 ft · 32 sec
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20
Merge slight left
57.2 mi · 1 hr 1 min
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21
Continue straight
7.1 mi · 8 min
-
22
Keep slight left to continue on I 81 North, US 11 North: Roanoke
139.7 mi · 2 hr 34 min
-
23
Continue straight
1353 ft · 18 sec
-
24
Keep slight right to continue on I 64 East: Richmond
90 mi · 1 hr 38 min
-
25
Take the exit slight right toward I 295 North: Washington, Norfolk
1.2 mi · 2 min
-
26
Continue on Korean War Veterans Memorial Highway
22.9 mi · 25 min · Korean War Veterans Memorial Highway
-
27
Take the exit slight right toward I 64 East: Norfolk, Virginia Beach
1.3 mi · 3 min
-
28
Merge slight left
66.8 mi · 1 hr 15 min
-
29
Keep slight left to continue on Hampton Roads Beltway
104 m · 5 sec · Hampton Roads Beltway
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30
Continue on Hampton Roads Bridge-Tunnel
3.5 mi · 5 min · Hampton Roads Bridge-Tunnel
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31
Continue on Hampton Roads Beltway
6.7 mi · 9 min · Hampton Roads Beltway
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32
Take the exit slight right toward VA 194 South: Chesapeake Boulevard
1312 ft · 32 sec
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33
Turn straight onto Chesapeake Boulevard
2.1 mi · 3 min · Chesapeake Boulevard
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34
Turn straight
41 m · 8 sec
-
35
Turn left onto Ballentine Boulevard
1.1 mi · 2 min · Ballentine Boulevard
-
36
Turn right onto East Princess Anne Road
1.5 km · 2 min · East Princess Anne Road
-
37
Turn left onto Park Avenue
3186 ft · 1 min · Park Avenue
-
38
Turn left onto East Brambleton Avenue
1692 ft · 58 sec · East Brambleton Avenue
-
39
Continue on Campostella Road
1.1 km · 2 min · Campostella Road
-
40
Turn right onto Wilson Road
1.2 km · 1 min · Wilson Road
-
41
Continue on 22nd Street
1606 ft · 27 sec · 22nd Street
-
42
Continue on Poindexter Street
1391 ft · 29 sec · Poindexter Street
-
43
Turn right onto D Street
126 m · 18 sec · D Street
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44
Arrive at your destination
0 m · 1 sec · D Street
Car Route Details
A richer read on the saved driving route between Wise and Chesapeake.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
I 81 North
Keep slight left to continue on I 81 North, US 11 North: Roanoke
140 mi · 02h 34m
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 Wise and Sunny near Chesapeake.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Wise to Chesapeake?
The road trip is about 422.5 miles (679.9 km) and usually takes 07h 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?
Buena Vista is a useful midpoint, sitting about 226.7 miles from Wise and 195.7 miles from Chesapeake.
How much longer is the road route than the straight-line distance?
The direct path is about 348.3 miles (560.5 km), while the road route adds roughly 74.2 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 EDT. 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 $59.06 one way or $118.12 round trip. Estimated CO2 is about 132.5 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Wise and Sunny near Chesapeake.
Stop Ideas Near Buena Vista
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 Buena Vista.
Kemper Street station
Clifton Forge
Staunton station
Roanoke
Flight Path Map
This map shows the direct air route between Wise and Chesapeake. Straight-line distance: 348.25 mi (560.46 km).
#1 Wise
Place in Virginia
| Population | 2,885 |
| Coordinates | 36.9759300, -82.5757100 |
| Altitude | 747 |
| 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: 680 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 14h 04m |
| 40 mph (64.37 km/h) | 10h 33m |
| 50 mph (80.47 km/h) | 08h 26m |
| 60 mph (96.56 km/h) | 07h 02m |
| 70 mph (112.65 km/h) | 06h 02m |
| 80 mph (129 km/h) | 05h 16m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $59.06 | $118.12 |
| Mid-grade | $4.43 | $66.04 | $132.07 |
| Premium | $4.78 | $71.24 | $142.48 |
| Diesel | $5.62 | $83.85 | $167.71 |
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.