How far is Chesapeake, VA from Highland Springs, VA?
The driving distance from Chesapeake, VA to Highland Springs, VA is about 88.6 miles (142.6 km), with a travel time of about 01h 51m by car.
- The straight-line flight distance is about 76.7 miles (123.4 km).
- For a round trip, plan for roughly 03h 42m 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 01h 51m.
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.
Independent city in Virginia, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Rain Showers Likely
Chance Rain Showers
Driving Route Map
The map below follows the saved road route between Chesapeake and Highland Springs.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake and Highland Springs.
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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
64.7 mi · 1 hr 12 min
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17
Take the exit slight right toward VA 156 North: Sandston, Highland Springs
1804 ft · 49 sec
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18
Turn right onto South Airport Drive
2961 ft · 1 min · South Airport Drive
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19
Turn left onto East Nine Mile Road
1.2 km · 2 min · East Nine Mile Road
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20
Turn left onto South Holly Avenue
9 m · 1 sec · South Holly Avenue
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21
Arrive at your destination
0 m · 1 sec · South Holly Avenue
Car Route Details
A richer read on the saved driving route between Chesapeake and Highland Springs.
Straightforward drive
The saved road route has a manageable number of maneuvers and should be easy to follow with normal attention to signs.
Hampton Roads Beltway
Keep slight left
64.7 mi · 01h 12m
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 Chesapeake and Chance Rain Showers near Highland Springs.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chesapeake to Highland Springs?
The road trip is about 88.6 miles (142.6 km) and usually takes 01h 51m 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?
Williamsburg is a useful midpoint, sitting about 44.3 miles from Chesapeake and 44.3 miles from Highland Springs.
How much longer is the road route than the straight-line distance?
The direct path is about 76.7 miles (123.4 km), while the road route adds roughly 11.9 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 2:48 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $12.40 one way or $24.80 round trip. Estimated CO2 is about 27.8 kg one way.
What should you check before leaving?
Before you leave, expect Rain Showers Likely around Chesapeake and Chance Rain Showers near Highland Springs.
Stop Ideas Near Williamsburg
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
James City County
James City County Government Center
Legacy Hall
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Williamsburg.
Williamsburg Transportation Center
Newport News station
Norfolk
Petersburg station
Flight Path Map
This map shows the direct air route between Chesapeake and Highland Springs. Straight-line distance: 76.69 mi (123.42 km).
#1 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
#2 Highland Springs
Census designated place
| Population | 15,711 |
| Coordinates | 37.5459800, -77.3277600 |
| Altitude | 52 |
| Country | United States |
End: Highland Springs (-77.32776, 37.54598)
Estimated Travel Time
Distance: 143 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 57m |
| 40 mph (64.37 km/h) | 02h 12m |
| 50 mph (80.47 km/h) | 01h 46m |
| 60 mph (96.56 km/h) | 01h 28m |
| 70 mph (112.65 km/h) | 01h 15m |
| 80 mph (129 km/h) | 01h 06m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $12.40 | $24.80 |
| Mid-grade | $4.43 | $13.86 | $27.73 |
| Premium | $4.78 | $14.96 | $29.91 |
| Diesel | $5.62 | $17.60 | $35.21 |
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 19, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.