How far is Hillsville, VA from Chesapeake, VA?
The driving distance from Hillsville, VA to Chesapeake, VA is about 288.4 miles (464.1 km), with a travel time of about 05h 08m by car.
- The straight-line flight distance is about 246.8 miles (397.2 km).
- For a round trip, plan for roughly 10h 16m 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 05h 08m.
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 in Virginia, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Occasional Showers And Thunderstorms
Showers And Thunderstorms
Driving Route Map
The map below follows the saved road route between Hillsville and Chesapeake.
Turn-by-Turn Driving Directions
Step-by-step road directions between Hillsville and Chesapeake.
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1
Start on West Stuart Drive
22 m · 9 sec · West Stuart Drive
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2
Turn right onto South Main Street
1.4 mi · 2 min · South Main Street
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3
Take the ramp left toward US 58 East: Martinsville, Danville
1087 ft · 26 sec
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4
Merge slight left onto Hillsville Bypass
2.4 mi · 3 min · Hillsville Bypass
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5
Continue on Danville Pike
15.2 mi · 20 min · Danville Pike
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6
Continue on Jeb Stuart Highway
31.2 mi · 42 min · Jeb Stuart Highway
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7
Continue on A. L. Philpott Highway
8.4 mi · 11 min · A. L. Philpott Highway
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8
Take the exit right toward US 58 East, US 220 South
1637 ft · 40 sec
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9
Merge slight left onto William F Stone Highway
9.4 mi · 11 min · William F Stone Highway
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10
Keep slight right to continue on US 58 East: Danville
14.7 mi · 19 min
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11
Take the exit straight toward US 58 East
14.2 mi · 17 min
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12
Take the exit slight right toward US 58 East, US 360 East: South Boston
1586 ft · 39 sec
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13
Merge slight left onto South Boston Road
2.9 mi · 5 min · South Boston Road
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14
Continue on South Boston Highway
5.3 mi · 7 min · South Boston Highway
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15
Continue on Philpott Road
19.7 mi · 26 min · Philpott Road
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16
Continue on Bill Tuck Highway
18.8 mi · 24 min · Bill Tuck Highway
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17
Continue on Clarksville Bypass
3.6 mi · 5 min · Clarksville Bypass
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18
Keep slight right to continue on Clarksville Bypass
19.2 mi · 25 min · Clarksville Bypass
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19
Continue on Highway 1
3.5 mi · 5 min · Highway 1
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20
Continue on South Hill Bypass
3.3 mi · 5 min · South Hill Bypass
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21
Continue on East Atlantic Street
1.1 mi · 2 min · East Atlantic Street
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22
Continue on Highway 58
3.6 mi · 5 min · Highway 58
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23
Continue on Piney Pond Road
1.2 mi · 2 min · Piney Pond Road
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24
Continue on Governor Harrison Parkway
22.5 mi · 30 min · Governor Harrison Parkway
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25
Continue on Pleasant Shade Drive
6.4 mi · 9 min · Pleasant Shade Drive
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26
Continue on West Atlantic Street
5.1 mi · 7 min · West Atlantic Street
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27
Continue on Southampton Parkway
62.1 mi · 1 hr 21 min · Southampton Parkway
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28
Continue on West Military Highway
1.7 mi · 2 min · West Military Highway
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29
Take the exit slight right toward I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
1.2 km · 2 min
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30
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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31
Merge slight left onto Hampton Roads Beltway
3026 ft · 43 sec · Hampton Roads Beltway
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32
Take the exit slight left toward I 264 East: Portsmouth, Norfolk
1.2 km · 1 min
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33
Continue straight
3.7 mi · 5 min
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34
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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35
Keep slight right to continue on US 17: Frederick Boulevard
1070 ft · 28 sec
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36
Turn right onto Frederick Boulevard
1.2 mi · 2 min · Frederick Boulevard
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37
At the end of the road, turn left onto George Washington Highway
1964 ft · 50 sec · George Washington Highway
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38
Turn right onto Elm Avenue
1.3 km · 1 min · Elm Avenue
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39
Continue on South Norfolk Jordan Bridge
1.1 mi · 2 min · South Norfolk Jordan Bridge
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40
Turn straight onto Poindexter Street
1.1 km · 1 min · Poindexter Street
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41
Turn left onto D Street
126 m · 18 sec · D Street
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42
Arrive at your destination
0 m · 1 sec · D Street
Car Route Details
A richer read on the saved driving route between Hillsville 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.
Southampton Parkway
Continue on Southampton Parkway
62.1 mi · 01h 21m
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.
Occasional Showers And Thunderstorms leaving Hillsville and Showers And Thunderstorms near Chesapeake.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Hillsville to Chesapeake?
The road trip is about 288.4 miles (464.1 km) and usually takes 05h 08m 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?
Clarksville is a useful midpoint, sitting about 144 miles from Hillsville and 144.4 miles from Chesapeake.
How much longer is the road route than the straight-line distance?
The direct path is about 246.8 miles (397.2 km), while the road route adds roughly 41.6 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 6:44 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $40.32 one way or $80.65 round trip. Estimated CO2 is about 90.5 kg one way.
What should you check before leaving?
Before you leave, expect Occasional Showers And Thunderstorms around Hillsville and Showers And Thunderstorms near Chesapeake.
Stop Ideas Near Clarksville
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 Clarksville.
Danville
Durham
North Carolina State Fair station
Cary
Flight Path Map
This map shows the direct air route between Hillsville and Chesapeake. Straight-line distance: 246.78 mi (397.15 km).
#1 Hillsville
Town in Carroll County, Virginia, United States
| Population | 2,686 |
| Coordinates | 36.7626300, -80.7347900 |
| Altitude | 767 |
| 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: 464 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 09h 36m |
| 40 mph (64.37 km/h) | 07h 12m |
| 50 mph (80.47 km/h) | 05h 46m |
| 60 mph (96.56 km/h) | 04h 48m |
| 70 mph (112.65 km/h) | 04h 07m |
| 80 mph (129 km/h) | 03h 35m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $40.32 | $80.65 |
| Mid-grade | $4.43 | $45.09 | $90.17 |
| Premium | $4.78 | $48.64 | $97.28 |
| Diesel | $5.62 | $57.25 | $114.50 |
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 · May 25, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.