How far is Middletown, VA from Chesapeake, VA?
The driving distance from Middletown, VA to Chesapeake, VA is about 224.9 miles (361.9 km), with a travel time of about 03h 48m by car.
- The straight-line flight distance is about 187.7 miles (302.1 km).
- For a round trip, plan for roughly 07h 37m 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 48m.
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.
Driving Route Map
The map below follows the saved road route between Middletown and Chesapeake.
Turn-by-Turn Driving Directions
Step-by-step road directions between Middletown and Chesapeake.
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1
Start on Main Street
3186 ft · 2 min · Main Street
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2
Turn right onto Reliance Road
2007 ft · 48 sec · Reliance Road
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3
Take the ramp right
858 ft · 21 sec
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4
Merge slight left
1.5 mi · 2 min
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5
Take the exit slight left toward I 66 East: Front Royal, Washington
3068 ft · 1 min
-
6
Continue straight
28.1 mi · 30 min
-
7
Take the exit slight right toward US 17: Warrenton, Fredericksburg
1330 ft · 33 sec
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8
Keep slight right
545 ft · 13 sec
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9
Merge slight left onto Winchester Road
2.4 mi · 3 min · Winchester Road
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10
Continue on James Madison Highway
6.5 mi · 9 min · James Madison Highway
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11
Keep slight right to continue on Eastern Bypass
4.9 mi · 7 min · Eastern Bypass
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12
Continue on James Madison Highway
5.1 mi · 7 min · James Madison Highway
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13
Keep slight right to continue on US 17 South
26.8 mi · 39 min
-
14
Take the exit straight toward I 95 South, US 17 South: Richmond
47.9 mi · 53 min
-
15
Take the exit slight left toward I 295 South: Williamsburg, Norfolk, Va Beach
1.9 mi · 2 min
-
16
Merge slight right onto Korean War Veterans Memorial Highway
13 mi · 14 min · Korean War Veterans Memorial Highway
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17
Take the exit slight right toward I 64 East: Norfolk, Virginia Beach
1.3 mi · 3 min
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18
Merge slight left
66.8 mi · 1 hr 15 min
-
19
Keep slight left to continue on Hampton Roads Beltway
104 m · 5 sec · Hampton Roads Beltway
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20
Continue on Hampton Roads Bridge-Tunnel
3.5 mi · 5 min · Hampton Roads Bridge-Tunnel
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21
Continue on Hampton Roads Beltway
6.7 mi · 9 min · Hampton Roads Beltway
-
22
Take the exit slight right toward VA 194 South: Chesapeake Boulevard
1312 ft · 32 sec
-
23
Turn straight onto Chesapeake Boulevard
2.1 mi · 3 min · Chesapeake Boulevard
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24
Turn straight
41 m · 8 sec
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25
Turn left onto Ballentine Boulevard
1.1 mi · 2 min · Ballentine Boulevard
-
26
Turn right onto East Princess Anne Road
1.5 km · 2 min · East Princess Anne Road
-
27
Turn left onto Park Avenue
3186 ft · 1 min · Park Avenue
-
28
Turn left onto East Brambleton Avenue
1692 ft · 58 sec · East Brambleton Avenue
-
29
Continue on Campostella Road
1.1 km · 2 min · Campostella Road
-
30
Turn right onto Wilson Road
1.2 km · 1 min · Wilson Road
-
31
Continue on 22nd Street
1606 ft · 27 sec · 22nd Street
-
32
Continue on Poindexter Street
1391 ft · 29 sec · Poindexter Street
-
33
Turn right onto D Street
126 m · 18 sec · D Street
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34
Arrive at your destination
0 m · 1 sec · D Street
Car Route Details
A richer read on the saved driving route between Middletown 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 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.
Sunny leaving Middletown and Sunny near Chesapeake.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Middletown to Chesapeake?
The road trip is about 224.9 miles (361.9 km) and usually takes 03h 48m 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?
Ashland is a useful midpoint, sitting about 113 miles from Middletown and 111.8 miles from Chesapeake.
How much longer is the road route than the straight-line distance?
The direct path is about 187.7 miles (302.1 km), while the road route adds roughly 37.2 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 9:22 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $31.45 one way or $62.90 round trip. Estimated CO2 is about 70.6 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Middletown and Sunny near Chesapeake.
Stop Ideas Near Ashland
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 Ashland.
Ashland
Richmond Staples Mill Road station
Richmond Main Street Station
Petersburg station
Flight Path Map
This map shows the direct air route between Middletown and Chesapeake. Straight-line distance: 187.7 mi (302.07 km).
#1 Middletown
Town in Virginia, United States
| Population | 1,424 |
| Coordinates | 39.0276100, -78.2805600 |
| Altitude | 218 |
| 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: 362 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 07h 29m |
| 40 mph (64.37 km/h) | 05h 37m |
| 50 mph (80.47 km/h) | 04h 29m |
| 60 mph (96.56 km/h) | 03h 44m |
| 70 mph (112.65 km/h) | 03h 12m |
| 80 mph (129 km/h) | 02h 48m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $31.45 | $62.90 |
| Mid-grade | $4.43 | $35.17 | $70.33 |
| Premium | $4.78 | $37.94 | $75.87 |
| Diesel | $5.62 | $44.65 | $89.31 |
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 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.