How far is Chesapeake, VA from Orange County, VA?
The driving distance from Chesapeake, VA to Orange County, VA is about 158.8 miles (255.5 km), with a travel time of about 03h 33m by car.
- The straight-line flight distance is about 137.1 miles (220.6 km).
- For a round trip, plan for roughly 07h 06m 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 03h 33m.
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 southeastern Virginia, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Partly Sunny
Rain Showers Likely
Driving Route Map
The map below follows the saved road route between Chesapeake and Orange County.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake and Orange County.
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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
-
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
18.5 mi · 20 min · Korean War Veterans Memorial Highway
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20
Take the exit slight right toward US 33 West: Montpelier
2002 ft · 1 min
-
21
Turn straight onto Staples Mill Road
1089 ft · 19 sec · Staples Mill Road
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22
Continue on Mountain Road
17.5 mi · 25 min · Mountain Road
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23
Continue on Jefferson Highway
12.6 mi · 17 min · Jefferson Highway
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24
Turn right onto Pendleton Road
3.2 mi · 5 min · Pendleton Road
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25
Continue on Mineral Avenue
1.1 km · 1 min · Mineral Avenue
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26
Turn right onto East 1st Street
131 m · 20 sec · East 1st Street
-
27
Turn left onto Louisa Avenue
1694 ft · 41 sec · Louisa Avenue
-
28
Continue on Zachary Taylor Highway
5 mi · 7 min · Zachary Taylor Highway
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29
Turn right
33 m · 8 sec
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30
Turn left
28 m · 2 sec
-
31
Turn right onto Zachary Taylor Highway
9.2 mi · 13 min · Zachary Taylor Highway
-
32
Turn left onto Lahore Road
2.3 mi · 6 min · Lahore Road
-
33
Turn right onto Kendall Road
3.5 mi · 9 min · Kendall Road
-
34
Turn right onto Bickers Lane
1204 ft · 53 sec · Bickers Lane
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35
Arrive at your destination
0 m · 1 sec · Bickers Lane
Car Route Details
A richer read on the saved driving route between Chesapeake and Orange County.
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.
Partly Sunny leaving Chesapeake and Rain Showers Likely near Orange County.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chesapeake to Orange County?
The road trip is about 158.8 miles (255.5 km) and usually takes 03h 33m 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?
Windsor is a useful midpoint, sitting about 79.3 miles from Chesapeake and 79.5 miles from Orange County.
How much longer is the road route than the straight-line distance?
The direct path is about 137.1 miles (220.6 km), while the road route adds roughly 21.7 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 9:54 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $23.17 one way or $46.35 round trip. Estimated CO2 is about 49.8 kg one way.
What should you check before leaving?
Before you leave, expect Partly Sunny around Chesapeake and Rain Showers Likely near Orange County.
Stop Ideas Near Windsor
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Old City Hall
City of Richmond Virginia (City Hall)
City Hall
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Windsor.
Richmond Main Street Station
Richmond Staples Mill Road station
Petersburg station
Ashland
Flight Path Map
This map shows the direct air route between Chesapeake and Orange County. Straight-line distance: 137.1 mi (220.64 km).
#1 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
#2 Orange County
County in Virginia, United States
| Population | 37,695 |
| Coordinates | 38.2462400, -78.0134900 |
| Altitude | 146 |
| Country | United States |
End: Orange County (-78.01349, 38.24624)
Estimated Travel Time
Distance: 255 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 05h 17m |
| 40 mph (64.37 km/h) | 03h 58m |
| 50 mph (80.47 km/h) | 03h 10m |
| 60 mph (96.56 km/h) | 02h 38m |
| 70 mph (112.65 km/h) | 02h 16m |
| 80 mph (129 km/h) | 01h 58m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.14 | $23.17 | $46.35 |
| Mid-grade | $4.63 | $25.94 | $51.88 |
| Premium | $5.01 | $28.07 | $56.15 |
| Diesel | $6.21 | $34.79 | $69.57 |
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 · Oct 15, 2026