How far is Chesapeake, VA from Pennington Gap, VA?
The driving distance from Chesapeake, VA to Pennington Gap, VA is about 475 miles (764.5 km), with a travel time of about 09h 08m by car.
- The straight-line flight distance is about 373.6 miles (601.2 km).
- For a round trip, plan for roughly 18h 16m 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 09h 08m.
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.
Sunny
Driving Route Map
The map below follows the saved road route between Chesapeake and Pennington Gap.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake and Pennington Gap.
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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
22.6 mi · 25 min · Korean War Veterans Memorial Highway
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20
Keep slight right to continue on I 64 West: Charlottesville
2936 ft · 55 sec
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21
Merge slight left onto I 64 West: Charlottesville
120.3 mi · 2 hr 11 min
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22
Keep slight left
117.1 mi · 2 hr 10 min
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23
Continue straight
1.3 mi · 1 min
-
24
Keep slight left
73.9 mi · 1 hr 19 min
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25
Take the exit slight right toward US 11W South: Kingsport
1616 ft · 46 sec
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26
Merge slight left
9.5 mi · 11 min
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27
Turn right onto Ollis Bowers Hill Road
109 m · 22 sec · Ollis Bowers Hill Road
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28
Turn left onto Bloomingdale Pike
5.1 mi · 9 min · Bloomingdale Pike
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29
Turn right onto North John B Dennis Highway
778 ft · 14 sec · North John B Dennis Highway
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30
Continue on Wadlow Gap Highway
4.7 mi · 5 min · Wadlow Gap Highway
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31
Turn right onto Main Street
1352 ft · 27 sec · Main Street
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32
Continue on US Highway 23
11.4 mi · 15 min · US Highway 23
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33
Continue on Orby Cantrell Highway
2 mi · 3 min · Orby Cantrell Highway
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34
Continue on US Highway 23
4.2 mi · 5 min · US Highway 23
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35
Turn left onto Duff Patt Highway
4.7 mi · 7 min · Duff Patt Highway
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36
Continue on Wilderness Road
6 mi · 8 min · Wilderness Road
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37
Turn right
5.2 mi · 8 min
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38
Turn left onto East Morgan Avenue
1.2 km · 2 min · East Morgan Avenue
-
39
Turn left onto Joslyn Avenue
29 m · 4 sec · Joslyn Avenue
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40
Arrive at your destination
0 m · 1 sec · Joslyn Avenue
Car Route Details
A richer read on the saved driving route between Chesapeake and Pennington Gap.
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.
Sunny leaving Chesapeake and Sunny near Pennington Gap.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chesapeake to Pennington Gap?
The road trip is about 475 miles (764.5 km) and usually takes 09h 08m 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?
Glasgow is a useful midpoint, sitting about 237.3 miles from Chesapeake and 237.7 miles from Pennington Gap.
How much longer is the road route than the straight-line distance?
The direct path is about 373.6 miles (601.2 km), while the road route adds roughly 101.4 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 $66.39 one way or $132.77 round trip. Estimated CO2 is about 148.9 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Chesapeake and Sunny near Pennington Gap.
Stop Ideas Near Glasgow
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 Glasgow.
Kemper Street station
Clifton Forge
Roanoke
Staunton station
Flight Path Map
This map shows the direct air route between Chesapeake and Pennington Gap. Straight-line distance: 373.57 mi (601.2 km).
#1 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
#2 Pennington Gap
Town of the United States
| Population | 1,708 |
| Coordinates | 36.7584200, -83.0271100 |
| Altitude | 423 |
| Country | United States |
End: Pennington Gap (-83.02711, 36.75842)
Estimated Travel Time
Distance: 765 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 15h 49m |
| 40 mph (64.37 km/h) | 11h 52m |
| 50 mph (80.47 km/h) | 09h 30m |
| 60 mph (96.56 km/h) | 07h 55m |
| 70 mph (112.65 km/h) | 06h 47m |
| 80 mph (129 km/h) | 05h 55m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $66.39 | $132.77 |
| Mid-grade | $4.43 | $74.23 | $148.46 |
| Premium | $4.78 | $80.08 | $160.16 |
| Diesel | $5.62 | $94.26 | $188.52 |
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.