The drive from Chesapeake, VA to Bassett, VA covers 236 miles and takes about 5h 18m behind the wheel.
This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Portsmouth Boulevard, Highway 58, 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 Portsmouth Boulevard.
At current regular gas prices, budget about $36.91 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
118 miles from Chesapeake, VA
A natural place for your longest stop of the day
, about 2h 40m into the drive
.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 5h 18m. Total distance: 236 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 18m drive, comfortable solo distance.
Scenic Drive
Mixed drive route profile with national parks nearby.
Drive Character
The drive from Chesapeake, VA to Bassett, VA covers 236 miles and takes about 5h 18m, 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 42 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?
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 0.1 miles in near US 460; VA 166 / Poindexter Street.
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 19 significant decision points across 236 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 19 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 Bassett, VA, road signs point toward Danville and Martinsville.
Danville
141 mi in|~3h 10m|via US 58
Martinsville
191.9 mi in|~4h 17m|via US 58
Main Roads
Road
Distance
Duration
Portsmouth Boulevard
62.1 mi
1h 21m
Highway 58
41.2 mi
53m
Governor Harrison Parkway
22.5 mi
30m
Philpott Road
19.7 mi
25m
US 58
15.6 mi
20m
Danville Expressway
13.9 mi
16m
I 264
6.7 mi
9m
Pleasant Shade Drive
6.3 mi
8m
Longest stretch:
Portsmouth Boulevard
— 62.1 mi, about 1h 21m
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake, VA and Bassett, 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
3.5 mi·4 min·South Hill Bypass
21
Continue on US 1; US 58
3.2 mi·4 min·Highway 1
22
Continue on US 58
19 mi·24 min·Highway 58
23
Turn straight onto US 58
4.0 mi·5 min·Clarksville Bypass
Toward US 58 West, US 15 South, VA 49 South: South Boston, DanvilleUse the straight lane.
24
Continue on US 58; VA 49
19 mi·24 min·Highway 58
Use the left lane.
25
Continue on US 58; US 360
20 mi·25 min·Philpott Road
26
Continue on US 58; US 360
5.3 mi·7 min·South Boston Highway
27
Continue on US 58; US 360
3.1 mi·5 min·South Boston Road
28
Take the ramp onto US 58
0.3 mi·39 sec·US 58
Toward US 29 South, US 58 West: Greesboro, Martinsville
29
Merge onto US 29; US 58
14 mi·16 min·Danville Expressway
30
Keep slight left at fork onto US 58
15 mi·20 min·US 58
31
Continue on US 58 BUS
3.6 mi·5 min·A L Philpott Highway
Toward US 58 West: Business, Martinsville
32
Continue on US 58 BUS; VA 57
0.9 mi·1 min·East Church Street
33
Turn right onto Hooker Street
0.3 mi·45 sec·Hooker Street
34
Turn right onto Fairy Street
116 ft·4 sec·Fairy Street
35
Turn left onto VA 457
2.3 mi·3 min·Commonwealth Boulevard East
36
Turn right onto US 220 BUS
4.1 mi·6 min·Virginia Avenue
37
Continue on VA 57
1.2 mi·1 min·Fairy Stone Park Highway
Use the straight / right lanes.
38
Continue on VA 57
2.1 mi·3 min·Fairystone Park Highway
39
Continue on VA 57
0.2 mi·18 sec·Fairystone Parkway
40
Turn right onto County Road 673
111 ft·9 sec·County Road 673
41
Turn left onto SR 673
265 ft·11 sec·Sunset Drive
42
Arrive at destination
SR 673
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 118 miles from Chesapeake, VA, or about 2h 40m 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 52 miles or 1h 10m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 118 miles or 2h 40m 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 19m
Traffic, exits, and arrival timing usually matter more near Bassett, 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 236 miles and 5h 18m.
Your first comfortable stop window is around 52 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 118 mi from Chesapeake, VA
· 2h 40m 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...
14 mi from route
~34 min detour
Free
Park Closure: Road Closure and Fishing Pier Impact
Booker T. Washington was born a slave in April 1856 on the 207-acre farm of James Burroughs. After the Civil War, Washington became the first principal of Tuskegee Normal and Industrial School. Later...
28 mi from route
~71 min detour
Free
near mile 236
Park data from the National Park Service API. Alerts update every 2 hours.
Fuel & Cost
Regular Gas
$36.91 one way
$73.81 round trip
$3.97/gal25.4 MPG avg83 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.34
$40.35
$80.70
premium
$4.70
$43.68
$87.36
diesel
$5.61
$52.11
$104.21
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$37
Meals
$25–$50
Total
$62–$87
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 82.6 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $25 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
70.8
0
$24.78
$11.33
Efficient EV
59
0
$20.65
$9.44
EV Truck/SUV
94.4
1
$33.04
$15.10
Gas CO2
83 kg
EV CO2
28 kg (66% 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 15, 2026
Origin
Chesapeake, VA
Afternoon
in Chesapeake on Friday
Local time
3:40 PM
EDT
Current temp
52°F
Unavailable
Live forecast
Destination
Bassett, VA
Afternoon
in Bassett on Friday
Local time
3:40 PM
EDT
Current temp
48°F
Unavailable
Live forecast
81°F
Lawrenceville, VA
118 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
4 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
5h 18m 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 Chesapeake, VA to Bassett, VA covers 236 miles and takes about 5h 18m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Portsmouth Boulevard, Highway 58, Governor Harrison Parkway. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 118 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 $36.91 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 19 significant decision points across 236 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 Bassett, VA, road signs point toward Danville and Martinsville.
Yes. Nearby national parks include Fort Monroe National Monument and Booker T Washington National Monument.
How this page is built
Compiled by the Trip.ovh planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, EIA for fuel prices, and NPS for national parks. See our methodology for refresh cadence and limitations.
