How far is Orange County, VA from Chesapeake, VA?
The driving distance from Orange County, VA to Chesapeake, VA is about 159.4 miles (256.5 km), with a travel time of about 02h 57m by car.
- The straight-line flight distance is about 137.1 miles (220.6 km).
- For a round trip, plan for roughly 05h 54m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
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 02h 57m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
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.
Rain Showers Likely
Partly Sunny
Driving Route Map
The map below follows the saved road route between Orange County and Chesapeake.
Turn-by-Turn Driving Directions
Step-by-step road directions between Orange County and Chesapeake.
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1
Start on Bickers Lane
1204 ft · 58 sec · Bickers Lane
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2
Turn left onto Kendall Road
3.5 mi · 9 min · Kendall Road
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3
At the end of the road, turn left onto Lahore Road
2.3 mi · 6 min · Lahore Road
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4
Turn right onto Zachary Taylor Highway
9.2 mi · 13 min · Zachary Taylor Highway
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5
Turn right
58 m · 5 sec
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6
Turn right onto Zachary Taylor Highway
5 mi · 7 min · Zachary Taylor Highway
-
7
Continue on Louisa Avenue
1694 ft · 45 sec · Louisa Avenue
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8
At the end of the road, turn right onto East 1st Street
131 m · 22 sec · East 1st Street
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9
Turn left onto Mineral Avenue
1.1 km · 1 min · Mineral Avenue
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10
Continue on Pendleton Road
3.2 mi · 5 min · Pendleton Road
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11
At the end of the road, turn left onto Jefferson Highway
12.6 mi · 17 min · Jefferson Highway
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12
Continue on Mountain Road
17.5 mi · 25 min · Mountain Road
-
13
Continue on Staples Mill Road
2436 ft · 40 sec · Staples Mill Road
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14
Take the ramp slight right toward I 295: Washington, Norfolk
1528 ft · 52 sec
-
15
Merge slight left onto Korean War Veterans Memorial Highway
19.5 mi · 21 min · Korean War Veterans Memorial Highway
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16
Take the exit slight right toward I 64 East: Norfolk, Virginia Beach
1.3 mi · 3 min
-
17
Merge slight left
66.8 mi · 1 hr 15 min
-
18
Keep slight left to continue on Hampton Roads Beltway
104 m · 5 sec · Hampton Roads Beltway
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19
Continue on Hampton Roads Bridge-Tunnel
3.5 mi · 5 min · Hampton Roads Bridge-Tunnel
-
20
Continue on Hampton Roads Beltway
6.7 mi · 9 min · Hampton Roads Beltway
-
21
Take the exit slight right toward VA 194 South: Chesapeake Boulevard
1312 ft · 32 sec
-
22
Turn straight onto Chesapeake Boulevard
2.1 mi · 3 min · Chesapeake Boulevard
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23
Turn straight
41 m · 8 sec
-
24
Turn left onto Ballentine Boulevard
1.1 mi · 2 min · Ballentine Boulevard
-
25
Turn right onto East Princess Anne Road
1.5 km · 2 min · East Princess Anne Road
-
26
Turn left onto Park Avenue
3186 ft · 1 min · Park Avenue
-
27
Turn left onto East Brambleton Avenue
1692 ft · 58 sec · East Brambleton Avenue
-
28
Continue on Campostella Road
1.1 km · 2 min · Campostella Road
-
29
Turn right onto Wilson Road
1.2 km · 1 min · Wilson Road
-
30
Continue on 22nd Street
1606 ft · 27 sec · 22nd Street
-
31
Continue on Poindexter Street
1391 ft · 29 sec · Poindexter Street
-
32
Turn right onto D Street
126 m · 18 sec · D Street
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33
Arrive at your destination
0 m · 1 sec · D Street
Car Route Details
A richer read on the saved driving route between Orange County 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.
I 64 East
Merge slight left
66.8 mi · 01h 15m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Rain Showers Likely leaving Orange County and Partly Sunny near Chesapeake.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Orange County to Chesapeake?
The road trip is about 159.4 miles (256.5 km) and usually takes 02h 57m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Windsor is a useful midpoint, sitting about 80.2 miles from Orange County and 79.1 miles from Chesapeake.
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 22.3 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 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 12:36 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $23.26 one way or $46.51 round trip. Estimated CO2 is about 49.9 kg one way.
What should you check before leaving?
Before you leave, expect Rain Showers Likely around Orange County and Partly Sunny near Chesapeake.
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 Orange County and Chesapeake. Straight-line distance: 137.1 mi (220.64 km).
#1 Orange County
County in Virginia, United States
| Population | 37,695 |
| Coordinates | 38.2462400, -78.0134900 |
| Altitude | 146 |
| 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: 256 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 05h 18m |
| 40 mph (64.37 km/h) | 03h 59m |
| 50 mph (80.47 km/h) | 03h 11m |
| 60 mph (96.56 km/h) | 02h 39m |
| 70 mph (112.65 km/h) | 02h 16m |
| 80 mph (129 km/h) | 01h 59m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.14 | $23.26 | $46.51 |
| Mid-grade | $4.63 | $26.03 | $52.06 |
| Premium | $5.01 | $28.17 | $56.35 |
| Diesel | $6.21 | $34.91 | $69.82 |
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