How far is Orange, VA from Chesapeake, VA?
The driving distance from Orange, VA to Chesapeake, VA is about 169.8 miles (273.2 km), with a travel time of about 02h 49m by car.
- The straight-line flight distance is about 140.8 miles (226.6 km).
- For a round trip, plan for roughly 05h 38m 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 49m.
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.
Mostly Sunny
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Orange and Chesapeake.
Turn-by-Turn Driving Directions
Step-by-step road directions between Orange and Chesapeake.
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1
Start on East Main Street
33 m · 10 sec · East Main Street
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2
Turn left onto South Madison Road
1294 ft · 27 sec · South Madison Road
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3
At the end of the road, turn left onto Caroline Street
2328 ft · 1 min · Caroline Street
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4
Continue on James Madison Highway
7.9 mi · 12 min · James Madison Highway
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5
Continue on East Gordon Avenue
817 ft · 21 sec · East Gordon Avenue
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6
Enter the roundabout and take exit 3 toward the route
51 m · 2 sec
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7
Exit the roundabout
1.1 km · 1 min
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8
Turn slight right onto Martinsburg Avenue
2056 ft · 35 sec · Martinsburg Avenue
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9
Continue on James Madison Highway
11 mi · 16 min · James Madison Highway
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10
Take the ramp slight left
2073 ft · 51 sec
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11
Merge slight left
40 mi · 43 min
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12
Take the exit slight right toward I 295 North: Washington, Norfolk
1.2 mi · 2 min
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13
Continue on Korean War Veterans Memorial Highway
22.9 mi · 25 min · Korean War Veterans Memorial Highway
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14
Take the exit slight right toward I 64 East: Norfolk, Virginia Beach
1.3 mi · 3 min
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15
Merge slight left
66.8 mi · 1 hr 15 min
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16
Keep slight left to continue on Hampton Roads Beltway
104 m · 5 sec · Hampton Roads Beltway
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17
Continue on Hampton Roads Bridge-Tunnel
3.5 mi · 5 min · Hampton Roads Bridge-Tunnel
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18
Continue on Hampton Roads Beltway
6.7 mi · 9 min · Hampton Roads Beltway
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19
Take the exit slight right toward VA 194 South: Chesapeake Boulevard
1312 ft · 32 sec
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20
Turn straight onto Chesapeake Boulevard
2.1 mi · 3 min · Chesapeake Boulevard
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21
Turn straight
41 m · 8 sec
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22
Turn left onto Ballentine Boulevard
1.1 mi · 2 min · Ballentine Boulevard
-
23
Turn right onto East Princess Anne Road
1.5 km · 2 min · East Princess Anne Road
-
24
Turn left onto Park Avenue
3186 ft · 1 min · Park Avenue
-
25
Turn left onto East Brambleton Avenue
1692 ft · 58 sec · East Brambleton Avenue
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26
Continue on Campostella Road
1.1 km · 2 min · Campostella Road
-
27
Turn right onto Wilson Road
1.2 km · 1 min · Wilson Road
-
28
Continue on 22nd Street
1606 ft · 27 sec · 22nd Street
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29
Continue on Poindexter Street
1391 ft · 29 sec · Poindexter Street
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30
Turn right onto D Street
126 m · 18 sec · D Street
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31
Arrive at your destination
0 m · 1 sec · D Street
Car Route Details
A richer read on the saved driving route between Orange 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.
Mostly Sunny leaving Orange and Mostly Sunny near Chesapeake.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Orange to Chesapeake?
The road trip is about 169.8 miles (273.2 km) and usually takes 02h 49m 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 85.5 miles from Orange and 84.2 miles from Chesapeake.
How much longer is the road route than the straight-line distance?
The direct path is about 140.8 miles (226.6 km), while the road route adds roughly 29 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 12:52 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $23.73 one way or $47.45 round trip. Estimated CO2 is about 53.2 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Orange and Mostly Sunny near Chesapeake.
Stop Ideas Near Windsor
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Town Hall
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 and Chesapeake. Straight-line distance: 140.82 mi (226.62 km).
#1 Orange
Town in Orange County, Vermont, United States
| Population | 5,166 |
| Coordinates | 38.2454100, -78.1108300 |
| Altitude | 159 |
| 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: 273 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 05h 39m |
| 40 mph (64.37 km/h) | 04h 14m |
| 50 mph (80.47 km/h) | 03h 23m |
| 60 mph (96.56 km/h) | 02h 49m |
| 70 mph (112.65 km/h) | 02h 25m |
| 80 mph (129 km/h) | 02h 07m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $23.73 | $47.45 |
| Mid-grade | $4.43 | $26.53 | $53.06 |
| Premium | $4.78 | $28.62 | $57.24 |
| Diesel | $5.62 | $33.69 | $67.38 |
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 30, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.