Planning a trip from Gretna, VA, to Chesapeake, VA? This drive covers 210.3 miles and is estimated to take around 4 hours and 50 minutes, making it a manageable one-day journey. You'll primarily travel on roads like Southampton Parkway and Clarksville Bypass, with about 46% of the drive being on highways. With an estimated fuel cost of $33, it's an economical option for exploring within the Southeast region of Virginia. This route offers a mixed driving experience, so plan for a single day of travel to make the most of your time.
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
105.2 miles from Gretna, VA
A natural place for your longest stop of the day
, about 2h 27m into the drive
.
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
Bill Tuck Highway
18.1 mi
22m
Halifax Road
16.4 mi
23m
Chatham Road
12.9 mi
19m
Main Street
10.3 mi
14m
Pleasant Shade Drive
6.4 mi
8m
Longest stretch:
Southampton Parkway
— 62.1 mi, about 1h 20m
Turn-by-Turn Driving Directions
Step-by-step road directions between Gretna, VA and Chesapeake, VA.
1
Start on SR 792
0.1 mi·25 sec·Northside Drive
2
Turn left onto US 29 BUS
10 mi·14 min·Main Street
3
Take the exit
0.1 mi·23 sec
Toward VA 57
4
Turn left onto VA 57
14 mi·19 min·Halifax Road
5
Continue on VA 57
13 mi·19 min·Chatham Road
6
Continue on VA 360
3.5 mi·5 min·Mountain Road
7
At end of road, turn right onto US 501
0.4 mi·1 min·South Main Street
8
Continue on US 501
1.9 mi·3 min·Halifax Road
9
Turn left onto VA 129
0.9 mi·1 min·Old Halifax Road
10
Continue on VA 129
1.8 mi·3 min·North Main Street
11
Turn left onto VA 34
0.5 mi·1 min·Hodges Street
12
Turn right onto US 360
0.4 mi·39 sec·John Randolph Boulevard
13
Continue on US 360
0.3 mi·31 sec·James D Hagood Highway
14
Continue on US 360
0.4 mi·43 sec·John Randolph Boulevard
15
Turn left onto US 58
18 mi·22 min·Bill Tuck Highway
Use the left / straight lanes.
16
Continue on US 58; VA 49
3.6 mi·4 min·Clarksville Bypass
Use the straight lane.
17
Keep slight right at fork onto US 58
19 mi·24 min·Clarksville Bypass
Toward US 58 East: Boydton, South Hill
18
Continue on US 1; US 58
3.5 mi·4 min·Highway 1
19
Continue on US 58
3.3 mi·4 min·South Hill Bypass
20
Continue on US 58
1.1 mi·1 min·East Atlantic Street
21
Continue on US 58
3.6 mi·5 min·Highway 58
22
Continue on US 58
1.2 mi·2 min·Piney Pond Road
23
Continue on US 58
23 mi·30 min·Governor Harrison Parkway
24
Continue on US 58
6.4 mi·8 min·Pleasant Shade Drive
25
Continue on US 58
5.1 mi·6 min·West Atlantic Street
26
Continue on US 58
62 mi·1 hr 20 min·Southampton Parkway
Use the straight / slight right lanes.
27
Continue on US 13; US 58; US 460
1.7 mi·2 min·West Military Highway
28
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
29
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
30
Merge onto I 664; US 13; US 460
0.6 mi·42 sec·Hampton Roads Beltway
31
Take the exit
0.8 mi·1 min
Exit 15AToward I 264 East: Portsmouth, Norfolk
32
Continue on I 264
3.7 mi·4 min·I 264
Use the straight / slight right lanes.
33
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.
34
Keep slight right at fork
0.2 mi·28 sec
Exit 5Toward US 17: Frederick BoulevardUse the slight right lane.
35
Turn right onto US 17
1.2 mi·1 min·Frederick Boulevard
Use the right lane.
36
At end of road, turn left onto VA 141
0.4 mi·50 sec·George Washington Highway
37
Turn right onto VA 337
0.8 mi·1 min·Elm Avenue
Use the straight / left lanes.
38
Continue on VA 337
1.1 mi·2 min·South Norfolk Jordan Bridge
39
Turn straight onto VA 337
0.7 mi·1 min·Poindexter Street
Use the straight lane.
40
Turn left onto D Street
412 ft·18 sec·D Street
41
Arrive at destination
D Street
Trip Plan
Given the 4-hour 50-minute estimated duration, departing Gretna, VA, in the morning is recommended to reach Chesapeake, VA, with daylight to spare. While the drive is only 210.3 miles, consider one planned stop for fuel or a break, especially during the 62.1-mile stretch on Southampton Parkway. The fuel cost is estimated at a reasonable $33, so keeping your tank topped up shouldn't be a major concern. This single-day trip allows for flexibility; you can adjust your departure time slightly based on your personal schedule, making the most of the efficient route.
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 105.2 miles from Gretna, VA, or about 2h 27m 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 8m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 105.2 miles or 2h 27m 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 57m
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 Gretna, 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 Gretna, VA
This is one driving day of about 210.3 miles and 4h 50m.
Your first comfortable stop window is around 46 miles from Gretna, 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.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 20
5 decision points cluster between mile 69.9 and 205.8 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
6
69.9 mi into trip|~1h 39m 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
200.2 mi into trip|~4h 33m 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...
6
201.2 mi into trip|~4h 35m in
Take the exit toward I 264 East: Portsmouth, Norfolk
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Exit 15A
Toward I 264 East: Portsmouth, Norfolk
8
205.7 mi into trip|~4h 41m 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
205.8 mi into trip|~4h 42m 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
Fuel & Cost
Regular Gas
$32.89 one way
$65.77 round trip
$3.97/gal25.4 MPG avg74 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.34
$35.96
$71.92
premium
$4.70
$38.92
$77.84
diesel
$5.61
$46.43
$92.86
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$33
Meals
$25–$50
Total
$58–$83
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 73.6 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $22 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
63.1
0
$22.08
$10.09
Efficient EV
52.6
0
$18.40
$8.41
EV Truck/SUV
84.1
1
$29.44
$13.46
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 17, 2026
Origin
Gretna, VA
Late night
in Gretna on Tuesday
Local time
5:09 AM
EDT
Current temp
53°F
Unavailable
Live forecast
Destination
Chesapeake, VA
Late night
in Chesapeake on Tuesday
Local time
5:09 AM
EDT
Current temp
68°F
Mostly Clear
SW 7 to 10 mph3% chanceLive forecast
74°F
Lawrenceville, VA
105 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
15 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
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.
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 210.3
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...
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This 210.3-mile route presents a mixed driving profile, meaning you'll encounter a variety of road types. While 46% of the journey is on highways, expect to transition to other types of roads as well. The longest uninterrupted stretch you'll experience is 62.1 miles on Southampton Parkway, offering a good period of consistent travel. The overall character is designed for efficiency, balancing faster highway sections with potentially slower local road segments, creating a dynamic driving experience as you progress towards Chesapeake.
46% highway, the rest on surface roads — varied driving throughout.
41 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 62.1 mi on Southampton Parkway.
How Hard Is This Drive?
8/10
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 69.9 miles in near US 58 / Clarksville Bypass.
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 20 significant decision points across 210.3 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 69.9 miles (US 58 / Clarksville Bypass): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 200.2 miles (US 13; US 460): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 201.2 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Gretna, VA and Chesapeake, VA, road signs point toward Hill, Norfolk and Va Beach.
Chesapeake is a town of 245,000 people (2019) in the Hampton Roads region of Eastern Virginia. Chesapeake is a diverse city in which a few urban areas are located; it also has many square miles of protected farmland, forests, and wetlands, including a substantial portion of the Great Dismal Swamp National Wildlife Refuge.
Doable as a same-day drive at 4h 50m. Total distance: 210.3 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
4h 50m drive, comfortable solo distance.
Scenic Drive
Mixed highway & surface route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 62.1 miles on Southampton Parkway. The full list of main roads is in the Roads section above.
We did not find dedicated rest areas on this route. For a drive this long, plan bathroom and stretch breaks around gas stations, fast-food stops, or small-town downtowns — check the Nearby Places section for options.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Chesapeake, VA before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 1 meaningful breaks. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 69.9 miles (US 58 / Clarksville Bypass): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 200.2 miles (US 13; US 460): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 201.2 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Yes — Fort Monroe National Monument and Booker T Washington National Monument. See the National Parks section for detour distances and tips on detours.
Possible but tiring. At 4.8 hours each way, an in-and-out day trip would put you behind the wheel for 9.7 hours — manageable with a long break at Chesapeake, VA, but most travelers stay overnight.
