Chesapeake, VA to Stanleytown, VA is 234.1 miles and takes about 5h 15m via Highway 58, with a fuel budget near $36 and enough daylight to finish in a day. This trip stays within Virginia, moving from the Southeast region to the Southeast region. The route offers a mixed highway and surface road experience, ideal for a single-day excursion. With a recommended single day of travel, it's a straightforward drive for those looking to cover ground 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
117 miles from Chesapeake, VA
A natural place for your longest stop of the day
, about 2h 39m into the drive
.
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
Traffic on I-264
Hour-of-day weekday pattern from 6 FHWA count stations on your route.
Peak
4 PM
~2,452 veh/hr typical
· worst 2,835
Quietest
2 AM
~162 veh/hr
Peak-to-quiet ratio
15.1×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 52 weeks of 2023 FHWA Travel Monitoring Analysis System data. Weekday hours only (Mon–Fri).
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake, VA and Stanleytown, 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
0.4 mi·36 sec·Fairystone Park Highway
39
Arrive at destination
VA 57
Trip Plan
Given the 5h 15m estimated duration, leaving Chesapeake, VA in the morning should allow you to reach Stanleytown, VA with plenty of daylight to spare. Plan for one stop, perhaps around the halfway point, to stretch your legs and refuel if needed, especially since the longest continuous stretch is over 60 miles. The fuel cost is estimated at $36, so factor that into your budget. Keep an eye on your fuel gauge as you transition between highway and surface road sections, as services might be less frequent on the latter.
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 117 miles from Chesapeake, VA, or about 2h 39m 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 117 miles or 2h 39m 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 17m
Traffic, exits, and arrival timing usually matter more near Stanleytown, 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 234.1 miles and 5h 15m.
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.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 17
5 decision points cluster between mile 0.1 and 10.2 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
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...
Fuel & Cost
Regular Gas
$34.56 one way
$69.12 round trip
$3.75/gal25.4 MPG avg82 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.12
$37.98
$75.96
premium
$4.49
$41.40
$82.80
diesel
$4.80
$44.20
$88.41
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$35
Meals
$25–$50
Total
$60–$85
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 81.9 kg one way.
Prices: EIA weekly data, 2026-07-13.
Driving Electric?
About $25 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
70.2
0
$24.58
$11.24
Efficient EV
58.5
0
$20.48
$9.36
EV Truck/SUV
93.6
1
$32.77
$14.98
Gas CO2
82 kg
EV CO2
27 kg (67% 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 Jul 18, 2026
Origin
Chesapeake, VA
Late night
in Chesapeake on Sunday
Local time
4:15 AM
EDT
Current temp
97°F
Mostly Sunny
SW 13 mph13% chanceLive forecast
Flood Watch
Flood Watch issued July 18 at 11:43AM EDT until July 18 at 8:00PM EDT by NWS Baltimore MD/Washington DC
Special Weather Statement
Special Weather Statement issued July 18 at 11:43AM EDT by NWS Blacksburg VA
Destination
Stanleytown, VA
Late night
in Stanleytown on Sunday
Local time
4:15 AM
EDT
Current temp
93°F
Scattered Showers And Thunderstorms
W 9 mph40% chanceLive forecast
Flood Watch
Flood Watch issued July 18 at 11:43AM EDT until July 18 at 8:00PM EDT by NWS Baltimore MD/Washington DC
Special Weather Statement
Special Weather Statement issued July 18 at 11:43AM EDT by NWS Blacksburg VA
85°F
Henderson, NC
117 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 15m 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
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...
29 mi from route
~72 min detour
Free
near mile 234.1
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
About 45% of this 234.1-mile drive is on highways, with the remaining 55% on surface roads. You'll encounter a longest stretch of 62.1 miles on Portsmouth Boulevard before transitioning to other main roads. Expect a mix of driving conditions, from potentially busier highway segments to more rural cruising as you make your way across the state.
45% highway, the rest on surface roads — varied driving throughout.
39 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 62.1 mi on Portsmouth Boulevard.
How Hard Is This Drive?
9/10
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 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 17 significant decision points across 234.1 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.
Elevation Profile
Gently rolling terrain
1,006 ft11 ft
Total Climb
1,074 ft
Total Descent
321 ft
Highest Point
1,006 ft
~217.4 mi in
Elevation Range
995 ft
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 Stanleytown, 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
Detours Along the Way
Tagged by where each one fits in your drive — first break, midpoint, final stretch.
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.
Top landmarks
•Dismal Swamp Canal — canal in Virginia, United States of America
•Albemarle and Chesapeake Canal — canal in Chesapeake, Virginia
•South Norfolk Historic District — historic district in Virginia, United States
Doable as a same-day drive at 5h 15m. Total distance: 234.1 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 15m 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 Portsmouth Boulevard. The full list of main roads is in the Roads section above.
Yes — we found about 10 rest areas or service plazas within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
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 Stanleytown, 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. There are 10 rest areas along the route for bathroom stops.
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.
Yes — Fort Monroe National Monument and Booker T Washington National Monument. See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 5.3 hours each way, a round trip means 10.5 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Stanleytown, VA before the return drive.
