The drive from Chesapeake, VA to South Hill, VA covers 116.5 miles and takes about 2h 39m behind the wheel.
This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Portsmouth Boulevard, Governor Harrison Parkway, I 264 for much of the mileage,
and the overall profile is turn-heavy local drive.
The longest uninterrupted segment is about 62.1 miles on Portsmouth Boulevard.
At current regular gas prices, budget about $18.22 one way before food or hotel costs.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Break Rhythm
1 planned break
A short stop every 2 to 3 hours is enough for this drive.
Midpoint
58.2 miles from Chesapeake, VA
A natural place for your longest stop of the day
, about 1h 18m into the drive
.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 2h 39m. Total distance: 116.5 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
2h 39m drive, comfortable solo distance.
Scenic Drive
Turn-heavy local drive route profile with national parks nearby.
Drive Character
Expect a 2h 39m drive with frequent turns across 116.5 miles of local and secondary roads.
This route has more turning and local-road decision points than a simple highway run.
There are about 21 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Portsmouth Boulevard is the longest continuous segment at about 62.1 miles.
How Hard Is This Drive?
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 0.1 miles in near US 460; VA 166 / Poindexter Street.
Driving Effort8/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This is a demanding drive. With 10 significant decision points across 116.5 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 0.1 miles (US 460; VA 166 / Poindexter Street): Complex interchange - multiple decisions in a short stretch; at 1.8 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 1.9 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Critical Maneuvers
5 of 10 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
6
0.1 mi into trip|~0m in|US 460; VA 166 / Poindexter Street
At end of road, turn right onto US 460; VA 166 / Poindexter Street
Complex interchange - multiple decisions in a short stretch
9
1.8 mi into trip|~2m in
Keep slight right at fork toward I 264 West Toll: Downtown Tunnel, Portsmouth
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 6A
Toward I 264 West Toll: Downtown Tunnel, Portsm...
7
1.9 mi into trip|~2m in
Keep slight left at fork toward I 264 West Toll: Tunnel
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / slight right lanes.
Toward I 264 West Toll: Tunnel
8
9.2 mi into trip|~13m in
Keep slight right at fork toward I 664: Bowers Hill, Suffolk, Richmond
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Toward I 664: Bowers Hill, Suffolk, Richmond
8
10.2 mi into trip|~15m in
Take the exit toward US 13, US 58, US 460, VA 191 North: Suffolk, Military Highway
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 13A-B
Toward US 13, US 58, US 460, VA 191 North: Suff...
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Chesapeake, VA and South Hill, VA, road signs point toward Suffolk, Richmond and Military Highway.
Suffolk
9.2 mi in|~13m
Richmond
9.2 mi in|~13m
Military Highway
10.2 mi in|~15m
Main Roads
Road
Distance
Duration
Portsmouth Boulevard
62.1 mi
1h 21m
Governor Harrison Parkway
22.5 mi
30m
I 264
6.7 mi
9m
Pleasant Shade Drive
6.3 mi
8m
Courtland Road
5.2 mi
7m
Highway 58
3.5 mi
5m
West Military Highway
2.4 mi
3m
East Atlantic Street
2.2 mi
5m
Longest stretch:
Portsmouth Boulevard
— 62.1 mi, about 1h 21m
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake, VA and South Hill, VA.
1
Start on D Street
412 ft·20 sec·D Street
2
At end of road, turn right onto US 460; VA 166
0.3 mi·29 sec·Poindexter Street
3
Take the ramp
0.2 mi·18 sec
Toward I 464 North
4
Merge onto I 464
1.2 mi·1 min·I 464
5
Keep slight right at fork
0.1 mi·14 sec
Exit 6AToward I 264 West Toll: Downtown Tunnel, PortsmouthUse the slight right lane.
6
Keep slight left at fork
0.5 mi·1 min
Toward I 264 West Toll: TunnelUse the slight left / slight right lanes.
7
Merge onto I 264; US 460 ALT
6.7 mi·9 min·I 264; US 460 ALT
Use the straight / slight right lanes.
8
Keep slight right at fork
0.6 mi·47 sec
Toward I 664: Bowers Hill, Suffolk, RichmondUse the slight right lane.
9
Merge onto I 664
0.4 mi·31 sec·Hampton Roads Beltway
10
Take the exit
0.3 mi·54 sec
Exit 13A-BToward US 13, US 58, US 460, VA 191 North: Suffolk, Military HighwayUse the slight right lane.
11
Keep slight left at fork
0.6 mi·1 min
12
Continue on US 13; US 58; US 460
2.4 mi·3 min·West Military Highway
13
Continue on US 13; US 58; US 460
62 mi·1 hr 21 min·Portsmouth Boulevard
Use the straight / right lanes.
14
Continue on US 58
5.2 mi·7 min·Courtland Road
15
Continue on US 58
6.3 mi·8 min·Pleasant Shade Drive
16
Continue on US 58
23 mi·30 min·Governor Harrison Parkway
17
Continue on US 58
1.2 mi·2 min·Piney Pond Road
18
Continue on US 58
3.5 mi·5 min·Highway 58
19
Continue on US 58
1.1 mi·1 min·East Atlantic Street
20
Continue on US 58 BUS
1.1 mi·3 min·East Atlantic Street
21
Arrive at destination
US 58 BUS
Trip Plan
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 58.2 miles from Chesapeake, VA, or about 1h 18m 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 26 miles or 36m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 58.2 miles or 1h 18m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 2h 8m
Traffic, exits, and arrival timing usually matter more near South Hill, VA than in the middle of the route.
Before You Leave
+
Open the route before leaving Chesapeake, 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 Chesapeake, VA
This is one driving day of about 116.5 miles and 2h 39m.
Your first comfortable stop window is around 26 miles from Chesapeake, 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 Portsmouth Boulevard for about 62.1 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 58.2 mi from Chesapeake, VA
· 1h 18m into the drive
Place data sourced from public business listings. Hours and availability may vary.
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...
13 mi from route
~33 min detour
Free
near mile 4
Park Closure: Road Closure and Fishing Pier Impact
Station data from NREL Alternative Fuel Stations database.
Driving Electric?
About $12 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
34.9
0
$12.23
$5.59
Efficient EV
29.1
0
$10.19
$4.66
EV Truck/SUV
46.6
0
$16.31
$7.46
Gas CO2
41 kg
EV CO2
14 kg (66% less)
This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.
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 16, 2026
Origin
Chesapeake, VA
Late night
in Chesapeake on Friday
Local time
1:20 AM
EDT
Current temp
93°F
Mostly Sunny
SW 14 mph0% chanceLive forecast
Destination
South Hill, VA
Late night
in South Hill on Friday
Local time
1:20 AM
EDT
Current temp
56°F
Unavailable
Live forecast
52°F
Waverly, VA
58 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
37 degrees cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
2h 39m on the road
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
Frequently Asked Questions
The drive from Chesapeake, VA to South Hill, VA covers 116.5 miles and takes about 2h 39m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Portsmouth Boulevard, Governor Harrison Parkway, I 264. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 58.2 miles from Chesapeake, VA. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $18.22 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.
Plan about 1 meaningful break for fuel, food, or rest. A short stop every 2 to 3 hours is enough for this drive.
This is a demanding drive. With 10 significant decision points across 116.5 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 0.1 miles (US 460; VA 166 / Poindexter Street): Complex interchange - multiple decisions in a short stretch; at 1.8 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 1.9 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Between Chesapeake, VA and South Hill, VA, road signs point toward Suffolk, Richmond and Military Highway.
