The drive from Chesapeake, VA to Gretna, VA covers 211.1 miles and takes about 4h 50m 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 $33.01 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
105.6 miles from Chesapeake, VA
A natural place for your longest stop of the day
, about 2h 22m into the drive
.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 4h 50m. Total distance: 211.1 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
4h 50m drive, comfortable solo distance.
Scenic Drive
Mixed drive route profile with national parks nearby.
Drive Character
The drive from Chesapeake, VA to Gretna, VA covers 211.1 miles and takes about 4h 50m, 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 39 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 20 significant decision points across 211.1 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 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 20 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.
On the drive from Chesapeake, VA to Gretna, VA, road signs begin pointing toward Danville along the way.
Danville
141 mi in|~3h 10m|via US 58
Main Roads
Road
Distance
Duration
Portsmouth Boulevard
62.1 mi
1h 21m
Highway 58
40.4 mi
51m
Governor Harrison Parkway
22.5 mi
30m
Halifax Road
16.3 mi
22m
Chatham Road
12.9 mi
19m
US 29
8 mi
9m
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 Gretna, 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
18 mi·22 min·Highway 58
25
Turn right onto US 360
1.1 mi·2 min·John Randolph Boulevard
26
Turn left onto VA 34
0.6 mi·1 min·Hodges Street
27
At end of road, turn right onto VA 129
1.8 mi·3 min·North Main Street
28
Continue on VA 129
0.9 mi·1 min·Old Halifax Road
29
Take the ramp
266 ft·7 sec
30
Merge onto US 501
1.9 mi·3 min·Halifax Road
31
Continue on US 501
0.4 mi·1 min·South Main Street
32
Turn left onto VA 360
3.5 mi·5 min·Mountain Road
33
Turn right onto VA 57
13 mi·19 min·Chatham Road
34
Continue on VA 57
14 mi·19 min·Halifax Road
35
Take the ramp
0.2 mi·22 sec
Toward US 29 North
36
Merge onto US 29
8.0 mi·9 min·US 29
37
Keep slight right at fork onto US 29 BUS
2.2 mi·4 min·US 29 BUS
Toward US 29 Business North: Gretna
38
Turn right onto SR 792
0.1 mi·19 sec·Northside Drive
39
Arrive at destination
SR 792
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 105.6 miles from Chesapeake, VA, or about 2h 22m 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 46 miles or 1h 2m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 105.6 miles or 2h 22m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 3h 55m
Traffic, exits, and arrival timing usually matter more near Gretna, 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 211.1 miles and 4h 50m.
Your first comfortable stop window is around 46 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 105.6 mi from Chesapeake, VA
· 2h 22m into the drive
The midpoint is around 105.6 miles from Chesapeake, VA, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel check
Top up before Portsmouth Boulevard if your tank is already low. That segment runs about 62.1 miles.
Arriving in Gretna, VA
The final approach into Gretna, 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 Gretna, 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
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...
23 mi from route
~59 min detour
Free
near mile 211.1
Station data from NREL Alternative Fuel Stations database.
Driving Electric?
About $22 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
63.3
0
$22.17
$10.13
Efficient EV
52.8
0
$18.47
$8.44
EV Truck/SUV
84.4
1
$29.55
$13.51
Gas CO2
74 kg
EV CO2
25 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 15, 2026
Origin
Chesapeake, VA
Late night
in Chesapeake on Saturday
Local time
12:09 AM
EDT
Current temp
52°F
Unavailable
Live forecast
Destination
Gretna, VA
Late night
in Gretna on Saturday
Local time
12:09 AM
EDT
Current temp
48°F
Unavailable
Live forecast
81°F
Lawrenceville, VA
106 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
4h 50m 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 Gretna, VA covers 211.1 miles and takes about 4h 50m 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 105.6 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 $33.01 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 20 significant decision points across 211.1 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 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.
On the drive from Chesapeake, VA to Gretna, VA, road signs begin pointing toward Danville along the way.
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, NREL for EV charging, and NPS for national parks. See our methodology for refresh cadence and limitations.
