Stuart, VA to Chesapeake, VA is 252.5 miles and takes about 5h 37m via Southampton Parkway and US 58, with a fuel budget near $39 and enough daylight to finish in a day. This trip stays within Virginia, connecting the Southeast region. You'll find a mix of highway and surface roads, making for a varied driving experience. With a recommended one-day drive, this route is manageable for most drivers looking to get from point A to B efficiently.
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
126.2 miles from Stuart, VA
A natural place for your longest stop of the day
, about 2h 44m into the drive
.
Main Roads
Road
Distance
Duration
Southampton Parkway
62.1 mi
1h 20m
US 58
29.4 mi
37m
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
Jeb Stuart Highway
14 mi
18m
William F Stone Highway
9.4 mi
10m
Longest stretch:
Southampton Parkway
— 62.1 mi, about 1h 20m
Turn-by-Turn Driving Directions
Step-by-step road directions between Stuart, VA and Chesapeake, VA.
1
Start on US 58 BUS
0.5 mi·1 min·East Blue Ridge Street
2
Turn right onto US 58
14 mi·18 min·Jeb Stuart Highway
3
Continue on US 58
8.4 mi·11 min·A. L. Philpott Highway
4
Take the exit onto US 58
0.3 mi·40 sec·US 58
Toward US 58 East, US 220 South
5
Merge onto US 58; US 220
9.4 mi·10 min·William F Stone Highway
6
Keep slight right at fork onto US 58
15 mi·19 min·US 58
Toward US 58 East: DanvilleUse the slight right lane.
7
Take the exit onto US 58
14 mi·17 min·US 58
Toward US 58 East
8
Take the exit onto US 58
0.3 mi·38 sec·US 58
Toward US 58 East, US 360 East: South Boston
9
Merge onto US 58; US 360
2.9 mi·5 min·South Boston Road
Use the straight lane.
10
Continue on US 58; US 360
5.3 mi·7 min·South Boston Highway
11
Continue on US 58; US 360
20 mi·25 min·Philpott Road
12
Continue on US 58; US 360
19 mi·24 min·Bill Tuck Highway
13
Continue on US 58; VA 49
3.6 mi·4 min·Clarksville Bypass
Use the straight lane.
14
Keep slight right at fork onto US 58
19 mi·24 min·Clarksville Bypass
Toward US 58 East: Boydton, South Hill
15
Continue on US 1; US 58
3.5 mi·4 min·Highway 1
16
Continue on US 58
3.3 mi·4 min·South Hill Bypass
17
Continue on US 58
1.1 mi·1 min·East Atlantic Street
18
Continue on US 58
3.6 mi·5 min·Highway 58
19
Continue on US 58
1.2 mi·2 min·Piney Pond Road
20
Continue on US 58
23 mi·30 min·Governor Harrison Parkway
21
Continue on US 58
6.4 mi·8 min·Pleasant Shade Drive
22
Continue on US 58
5.1 mi·6 min·West Atlantic Street
23
Continue on US 58
62 mi·1 hr 20 min·Southampton Parkway
Use the straight / slight right lanes.
24
Continue on US 13; US 58; US 460
1.7 mi·2 min·West Military Highway
25
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
26
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
27
Merge onto I 664; US 13; US 460
0.6 mi·42 sec·Hampton Roads Beltway
28
Take the exit
0.8 mi·1 min
Exit 15AToward I 264 East: Portsmouth, Norfolk
29
Continue on I 264
3.7 mi·4 min·I 264
Use the straight / slight right lanes.
30
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.
31
Keep slight right at fork
0.2 mi·28 sec
Exit 5Toward US 17: Frederick BoulevardUse the slight right lane.
32
Turn right onto US 17
1.2 mi·1 min·Frederick Boulevard
Use the right lane.
33
At end of road, turn left onto VA 141
0.4 mi·50 sec·George Washington Highway
34
Turn right onto VA 337
0.8 mi·1 min·Elm Avenue
Use the straight / left lanes.
35
Continue on VA 337
1.1 mi·2 min·South Norfolk Jordan Bridge
36
Turn straight onto VA 337
0.7 mi·1 min·Poindexter Street
Use the straight lane.
37
Turn left onto D Street
412 ft·18 sec·D Street
38
Arrive at destination
D Street
Trip Plan
Given the 5h 37m estimated duration, leaving Stuart, VA in the morning is a good plan to ensure you arrive with daylight. The route includes a stop at the 62.1-mile mark on Southampton Parkway, which is a good point to consider for a break. Keep an eye on your fuel gauge, as the estimated cost is $39 for the 252.5 miles. Since this is a single-day trip, you have flexibility, but try to stay aware of traffic conditions as you get closer to the Chesapeake area.
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 126.2 miles from Stuart, VA, or about 2h 44m 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 56 miles or 1h 12m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 126.2 miles or 2h 44m 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 33m
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 Stuart, 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 Stuart, VA
This is one driving day of about 252.5 miles and 5h 37m.
Your first comfortable stop window is around 56 miles from Stuart, 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 19
5 decision points cluster between mile 22.9 and 248 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
6
22.9 mi into trip|~31m in|US 58
Take the exit onto US 58 toward US 58 East, US 220 South
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Toward US 58 East, US 220 South
7
32.6 mi into trip|~42m in|US 58
Keep slight right at fork onto US 58 toward US 58 East: Danville
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Toward US 58 East: Danville
6
61.8 mi into trip|~1h 19m 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.
8
247.8 mi into trip|~5h 28m 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
248 mi into trip|~5h 28m 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
$39.49 one way
$78.97 round trip
$3.97/gal25.4 MPG avg88 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.34
$43.17
$86.35
premium
$4.70
$46.73
$93.46
diesel
$5.61
$55.75
$111.50
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$39
Meals
$25–$50
Total
$64–$89
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 88.3 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $27 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
75.8
0
$26.51
$12.12
Efficient EV
63.1
0
$22.09
$10.10
EV Truck/SUV
101
1
$35.35
$16.16
Gas CO2
88 kg
EV CO2
30 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 20, 2026
Origin
Stuart, VA
Morning
in Stuart on Tuesday
Local time
6:39 AM
EDT
Current temp
70°F
Unavailable
Live forecast
Destination
Chesapeake, VA
Morning
in Chesapeake on Tuesday
Local time
6:39 AM
EDT
Current temp
73°F
Unavailable
Live forecast
74°F
Henderson, NC
126 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
3 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 37m 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 252.5
Park Closure: Road Closure and Fishing Pier Impact
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
About half of this 252.5-mile drive, roughly 50%, is on highways. You'll encounter a longest stretch of 62.1 miles on Southampton Parkway before transitioning to surface roads. Expect a blend of cruising on faster parkways and navigating through more built-up areas as you approach your destination. The change from highway to surface roads will be noticeable as you get closer to Chesapeake.
50% highway, the rest on surface roads — varied driving throughout.
38 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?
10/10
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 22.9 miles in near US 58.
Driving Effort10/10
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 252.5 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 22.9 miles (US 58): Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one; at 32.6 miles (US 58): Highway fork - watch signs carefully. Lane positioning matters here; at 61.8 miles (US 58; US 360 / South Boston Road): Merge point - match speed before joining. Lane positioning matters here.
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 Stuart, VA to Chesapeake, VA, road signs begin pointing toward Hill along the way.
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 5h 37m. Total distance: 252.5 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 37m 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 22.9 miles (US 58): Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one; at 32.6 miles (US 58): Highway fork - watch signs carefully. Lane positioning matters here; at 61.8 miles (US 58; US 360 / South Boston Road): Merge point - match speed before joining. Lane positioning matters here.
Yes — Fort Monroe National Monument. See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 5.6 hours each way, a round trip means 11.2 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Chesapeake, VA before the return drive.
