The drive from Martinsville, VA to Chesapeake, VA covers 225.1 miles and takes about 5h 4m behind the wheel.
This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Southampton Parkway, Clarksville Bypass, Governor Harrison Parkway for much of the mileage,
and the overall profile is mixed drive.
The longest uninterrupted segment is about 62.1 miles on Southampton Parkway.
At current regular gas prices, budget about $35.20 one way before food or hotel costs.
Trip Pace
Same-day drive is realistic
A same-day return is possible, but it will make for a full day on the road.
Break Rhythm
1 planned break
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
112.6 miles from Martinsville, VA
A natural place for your longest stop of the day
, about 2h 30m into the drive
.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 5h 4m. Total distance: 225.1 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 4m drive, comfortable solo distance.
Scenic Drive
Mixed drive route profile with national parks nearby.
Drive Character
The drive from Martinsville, VA to Chesapeake, VA covers 225.1 miles and takes about 5h 4m, using a mix of highways and local roads.
Expect a mix of faster highway mileage and slower local approaches near the beginning or end.
There are about 36 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Southampton Parkway is the longest continuous segment at about 62.1 miles.
How Hard Is This Drive?
This route mixes highway mileage with some local-road sections near the start or finish. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 34.4 miles in near US 58; US 360 / South Boston Road.
Driving Effort9/10
High effort - long or complex enough to need steady focus all day
Balances navigation complexity with total wheel time.
This is a demanding drive. With 16 significant decision points across 225.1 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 34.4 miles (US 58; US 360 / South Boston Road): Merge point - match speed before joining. Lane positioning matters here; at 84.7 miles (US 58 / Clarksville Bypass): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 215 miles (US 13; US 460): Highway fork - watch signs carefully. Multiple destination signs - pick the right one.
Critical Maneuvers
5 of 16 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
6
34.4 mi into trip|~46m in|US 58; US 360 / South Boston Road
Merge onto US 58; US 360 / South Boston Road
Merge point - match speed before joining. Lane positioning matters here
Use the straight lane.
6
84.7 mi into trip|~1h 53m in|US 58 / Clarksville Bypass
Keep slight right at fork onto US 58 / Clarksville Bypass toward US 58 East: Boydton, South Hill
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Toward US 58 East: Boydton, South Hill
6
215 mi into trip|~4h 47m in|US 13; US 460
Keep slight left at fork onto US 13; US 460 toward I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Toward I 264 East, I 64, US 13 North: Portsmout...
8
220.5 mi into trip|~4h 55m in
Take the exit toward VA 164 West, US 17: Martin Luther King Jr Expressway, Norfolk, Frederick Boulevard
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 6; 5
Toward VA 164 West, US 17: Martin Luther King J...
9
220.7 mi into trip|~4h 55m in
Keep slight right at fork toward US 17: Frederick Boulevard
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Exit 5
Toward US 17: Frederick Boulevard
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
On the drive from Martinsville, VA to Chesapeake, VA, road signs begin pointing toward Hill along the way.
Hill
84.7 mi in|~1h 53m|via US 58
Main Roads
Road
Distance
Duration
Southampton Parkway
62.1 mi
1h 20m
Clarksville Bypass
22.9 mi
29m
Governor Harrison Parkway
22.5 mi
30m
Philpott Road
19.7 mi
25m
Bill Tuck Highway
18.8 mi
24m
US 58
14.5 mi
17m
A L Philpott Highway
9 mi
12m
Martinsville Highway
8.9 mi
11m
Longest stretch:
Southampton Parkway
— 62.1 mi, about 1h 20m
Turn-by-Turn Driving Directions
Step-by-step road directions between Martinsville, VA and Chesapeake, VA.
1
Start on Walnut Street
255 ft·14 sec·Walnut Street
2
At end of road, turn left onto East Church Street
2.0 mi·5 min·East Church Street
3
Continue on US 58 BUS; VA 57
9.0 mi·12 min·A L Philpott Highway
4
Continue on US 58
8.9 mi·11 min·Martinsville Highway
5
Take the exit onto US 58
14 mi·17 min·US 58
Toward US 58 East
6
Take the exit onto US 58
0.3 mi·38 sec·US 58
Toward US 58 East, US 360 East: South Boston
7
Merge onto US 58; US 360
2.9 mi·5 min·South Boston Road
Use the straight lane.
8
Continue on US 58; US 360
5.3 mi·7 min·South Boston Highway
9
Continue on US 58; US 360
20 mi·25 min·Philpott Road
10
Continue on US 58; US 360
19 mi·24 min·Bill Tuck Highway
11
Continue on US 58; VA 49
3.6 mi·4 min·Clarksville Bypass
Use the straight lane.
12
Keep slight right at fork onto US 58
19 mi·24 min·Clarksville Bypass
Toward US 58 East: Boydton, South Hill
13
Continue on US 1; US 58
3.5 mi·4 min·Highway 1
14
Continue on US 58
3.3 mi·4 min·South Hill Bypass
15
Continue on US 58
1.1 mi·1 min·East Atlantic Street
16
Continue on US 58
3.6 mi·5 min·Highway 58
17
Continue on US 58
1.2 mi·2 min·Piney Pond Road
18
Continue on US 58
23 mi·30 min·Governor Harrison Parkway
19
Continue on US 58
6.4 mi·8 min·Pleasant Shade Drive
20
Continue on US 58
5.1 mi·6 min·West Atlantic Street
21
Continue on US 58
62 mi·1 hr 20 min·Southampton Parkway
Use the straight / slight right lanes.
22
Continue on US 13; US 58; US 460
1.7 mi·2 min·West Military Highway
23
Take the exit onto US 13; US 460
0.7 mi·1 min·US 13; US 460
Toward I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
24
Keep slight left at fork onto US 13; US 460
0.4 mi·56 sec·US 13; US 460
Toward I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
25
Merge onto I 664; US 13; US 460
0.6 mi·42 sec·Hampton Roads Beltway
26
Take the exit
0.8 mi·1 min
Exit 15AToward I 264 East: Portsmouth, Norfolk
27
Continue on I 264
3.7 mi·4 min·I 264
Use the straight / slight right lanes.
28
Take the exit
0.2 mi·22 sec
Exit 6; 5Toward VA 164 West, US 17: Martin Luther King Jr Expressway, Norfolk, Frederick BoulevardUse the slight right lane.
29
Keep slight right at fork
0.2 mi·28 sec
Exit 5Toward US 17: Frederick BoulevardUse the slight right lane.
30
Turn right onto US 17
1.2 mi·1 min·Frederick Boulevard
Use the right lane.
31
At end of road, turn left onto VA 141
0.4 mi·50 sec·George Washington Highway
32
Turn right onto VA 337
0.8 mi·1 min·Elm Avenue
Use the straight / left lanes.
33
Continue on VA 337
1.1 mi·2 min·South Norfolk Jordan Bridge
34
Turn straight onto VA 337
0.7 mi·1 min·Poindexter Street
Use the straight lane.
35
Turn left onto D Street
412 ft·18 sec·D Street
36
Arrive at destination
D Street
Trip Plan
Morning Departure
An early start around 7-8 AM gets you there with plenty of daylight left.
Evening Departure
A late afternoon start means arriving after dark. Morning is better.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 112.6 miles from Martinsville, VA, or about 2h 30m into the drive.
The longest continuous stretch on this route runs about 62.1 miles.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 50 miles or 1h 8m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 112.6 miles or 2h 30m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 4h 7m
Traffic, exits, and arrival timing usually matter more near Chesapeake, VA than in the middle of the route.
Before You Leave
+
Open the route before leaving Martinsville, VA so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Martinsville, VA
This is one driving day of about 225.1 miles and 5h 4m.
Your first comfortable stop window is around 50 miles from Martinsville, VA.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 1 real break rather than only quick fuel stops.
The longest stretch is on Southampton Parkway for about 62.1 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 112.6 mi from Martinsville, VA
· 2h 30m into the drive
The midpoint is around 112.6 miles from Martinsville, VA, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel check
Top up before Southampton Parkway if your tank is already low. That segment runs about 62.1 miles.
Arriving in Chesapeake, VA
The final approach into Chesapeake, VA usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Chesapeake, VA.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
National Parks Near This Route
Worth a detour if your schedule allows.
Fort Monroe National Monument
National Monument
Fort Monroe's story spans from prehistory to the 2000s. Kecoughtan Indians occupied Old Point Comfort before the arrival of English colonists. The first enslaved Africans arrived in 1619. Those escapi...
14 mi from route
~34 min detour
Free
near mile 225.1
Park Closure: Road Closure and Fishing Pier Impact
Station data from NREL Alternative Fuel Stations database.
Driving Electric?
About $24 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
67.5
0
$23.64
$10.80
Efficient EV
56.3
0
$19.70
$9.00
EV Truck/SUV
90
1
$31.51
$14.41
Gas CO2
79 kg
EV CO2
26 kg (67% less)
Plan for 0 charging stops, roughly every 270 miles. Allow 25-40 minutes per stop at a DC fast charger.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive.
Forecast as of Apr 14, 2026
Origin
Martinsville, VA
Late night
in Martinsville on Friday
Local time
3:57 AM
EDT
Current temp
47°F
Unavailable
Live forecast
Destination
Chesapeake, VA
Late night
in Chesapeake on Friday
Local time
3:57 AM
EDT
Current temp
64°F
Partly Cloudy
SW 9 mph3% chanceLive forecast
81°F
Lawrenceville, VA
113 mi in
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
17 degrees warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
5h 4m on the road
An early start around 7-8 AM gets you there with plenty of daylight left.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
Frequently Asked Questions
The drive from Martinsville, VA to Chesapeake, VA covers 225.1 miles and takes about 5h 4m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Southampton Parkway, Clarksville Bypass, Governor Harrison Parkway. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 112.6 miles from Martinsville, VA. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $35.20 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
An early start around 7-8 AM gets you there with plenty of daylight left. A late afternoon start means arriving after dark. Morning is better.
Plan about 1 meaningful break for fuel, food, or rest. Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
This is a demanding drive. With 16 significant decision points across 225.1 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
The main spots that need attention: at 34.4 miles (US 58; US 360 / South Boston Road): Merge point - match speed before joining. Lane positioning matters here; at 84.7 miles (US 58 / Clarksville Bypass): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 215 miles (US 13; US 460): Highway fork - watch signs carefully. Multiple destination signs - pick the right one.
On the drive from Martinsville, VA to Chesapeake, VA, road signs begin pointing toward Hill along the way.
How this page is built
Compiled and maintained by the Trip.ovh planning team at COD Solutions Oy (Helsinki). Each route is built from authoritative open government and mapping datasets rather than crowdsourced reviews. Distances and geometry come from
OSRM
over
OpenStreetMap.
Fuel cost uses
EIA
weekly regional averages.
EV charging comes from the
NREL Alternative Fuels
dataset.
National park proximity is from the
NPS API.
Pages are published only after passing our data-quality checks; our
methodology page
documents refresh cadence, editorial standards, and known limitations.
