Crossing the Commonwealth from Clintwood to Chesapeake is a significant 464.9-mile journey that spans the state from the Appalachian mountains to the coast. You should budget approximately 9 hours and 5 minutes of driving time, making this a trek that is best split over two days to avoid fatigue. With a projected fuel cost of $74, the trip is manageable but requires careful planning. You will primarily utilize I-81, I-64, and the Korean War Veterans Memorial Highway to make your way across the Southeast. Because the route crosses the entire width of Virginia, an overnight stay allows you to enjoy the transition between regions rather than rushing through the interstate segments.
Trip Pace
Best split across 2 days
Treat the return leg as its own travel day rather than an afterthought.
Break Rhythm
2 planned breaks
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
232.5 miles from Clintwood, VA
A natural place for your longest stop of the day
, about 4h 39m into the drive
.
Main Roads
Road
Distance
Duration
I 81
196.9 mi
3h 35m
I 64
157.1 mi
2h 53m
Korean War Veterans Memorial Highway
22.9 mi
25m
Dante Mountain Road
13.9 mi
20m
US 19
12.7 mi
18m
Dante Road
8.9 mi
13m
Trail of the Lonesome Pine
7.9 mi
10m
I 77
7.1 mi
7m
Longest stretch:
I 81
— 196.9 mi, about 3h 35m
Turn-by-Turn Driving Directions
Step-by-step road directions between Clintwood, VA and Chesapeake, VA.
1
Start on Skeens Avenue
58 ft·9 sec·Skeens Avenue
2
Turn left onto SR 607
0.2 mi·23 sec·Clintwood Main Street
3
Enter roundabout onto VA 83
207 ft·3 sec·Dickenson Highway
4
Continue on VA 83
6.4 mi·9 min·Dickenson Highway
5
Turn sharp right onto VA 63
14 mi·20 min·Dante Mountain Road
6
Continue on VA 63
8.9 mi·13 min·Dante Road
7
Continue on VA 63
1.1 mi·1 min·Wise Street
8
Turn left onto VA 270
0.3 mi·50 sec·4th Avenue
9
At end of road, turn left onto US 58 ALT
0.2 mi·24 sec·Castlewood Drive
10
Continue on US 58 ALT
365 ft·6 sec·Trail of the Lonesome Pine
11
Continue on US 58 ALT
6.9 mi·9 min·US Highway 58 Alternate
12
Continue on US 58 ALT; VA 71
7.8 mi·10 min·Trail of the Lonesome Pine
13
Turn right onto US 19
13 mi·18 min·US 19
14
Turn left onto US 11
0.5 mi·1 min·West Main Street
15
Turn right onto Preston Street Southwest
0.2 mi·33 sec·Preston Street Southwest
16
At end of road, turn left onto Bradley Street Southwest
0.5 mi·1 min·Bradley Street Southwest
17
At end of road, turn right onto US 58 ALT; VA 75
0.6 mi·1 min·Cummings Street
Use the straight lane.
18
Take the exit
0.2 mi·31 sec
19
Merge onto I 81; US 58
57 mi·1 hr 1 min·I 81; US 58
Use the straight lane.
20
Continue on I 77; I 81; US 11; US 52
7.1 mi·7 min·I 77; I 81; US 11; US 52
21
Keep slight left at fork onto I 81; US 11
140 mi·2 hr 33 min·I 81; US 11
Toward I 81 North, US 11 North: RoanokeUse the straight lane.
22
Continue on I 64; I 81
0.3 mi·17 sec·I 64; I 81
23
Keep slight right at fork onto I 64
90 mi·1 hr 38 min·I 64
Toward I 64 East: RichmondUse the straight lane.
24
Take the exit
1.2 mi·1 min
Exit 177Toward I 295 North: Washington, NorfolkUse the slight right lane.
25
Continue on I 295
23 mi·25 min·Korean War Veterans Memorial Highway
Use the straight / slight right lanes.
26
Take the exit
1.3 mi·2 min
Exit 28AToward I 64 East: Norfolk, Virginia BeachUse the straight / slight right lanes.
27
Merge onto I 64
67 mi·1 hr 15 min·I 64
Use the straight / slight right lanes.
28
Keep slight left at fork onto I 64; US 60
342 ft·5 sec·Hampton Roads Beltway
29
Continue on I 64; US 60
3.5 mi·4 min·Hampton Roads Bridge-Tunnel
30
Continue on I 64; US 60
6.7 mi·8 min·Hampton Roads Beltway
Use the straight / slight right lanes.
31
Take the exit
0.2 mi·32 sec
Exit 278Toward VA 194 South: Chesapeake BoulevardUse the slight right lane.
32
Turn straight onto VA 194
2.1 mi·3 min·Chesapeake Boulevard
Use the left lane.
33
Turn straight
135 ft·7 sec
34
Turn left onto VA 247
1.1 mi·1 min·Ballentine Boulevard
35
Turn right onto VA 166
0.9 mi·1 min·East Princess Anne Road
36
Turn left onto VA 166
0.6 mi·1 min·Park Avenue
37
Turn left onto US 460; VA 166; VA 168
0.3 mi·57 sec·East Brambleton Avenue
Use the left / straight / right lanes.
38
Continue on US 460; VA 166; VA 168
0.7 mi·1 min·Campostella Road
39
Turn right onto US 460; VA 166
0.7 mi·1 min·Wilson Road
Use the right lane.
40
Continue on US 460; VA 166
0.3 mi·27 sec·22nd Street
41
Continue on US 460; VA 166
0.3 mi·29 sec·Poindexter Street
Use the straight lane.
42
Turn right onto D Street
412 ft·18 sec·D Street
43
Arrive at destination
D Street
Trip Plan
To make the most of this 464.9-mile haul, plan for at least two major stops to refresh yourself during the long hours behind the wheel. Departing early in the morning is your best strategy for navigating the high-traffic stretches of I-81 and I-64 more comfortably. Keep a close eye on your fuel gauge, especially during the long 196.9-mile interstate segment, to ensure you stay within your $74 budget without needing to hunt for stations in remote areas. Since this is a two-day trip, consider splitting your drive near the halfway point to balance your time on the road. Staying flexible with your departure time will help you avoid the worst congestion on the primary highways.
Morning Departure
Start early — leave by 6-7 AM to arrive at a reasonable hour.
Evening Departure
This is a long drive — plan for a morning departure or consider splitting it into two days.
This drive is better paced as a 2-day trip.
Plan roughly 2 meaningful breaks for fuel, food, and rest.
The halfway point lands around 232.5 miles from Clintwood, VA, or about 4h 39m into the drive.
The longest continuous stretch on this route runs about 196.9 miles.
Consider an overnight stop or starting very early.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 102 miles or 2h 16m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 232.5 miles or 4h 39m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Overnight split
Day 1 wrap after about 232.5 miles or 4h 39m
Stop before fatigue turns the last few hours into a grind. You want day two to start fresh, not just resumed.
Final approach
Final hour starts around 7h 50m
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 Clintwood, 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.
+
Pick one backup stop option before the midpoint in case traffic changes your pacing.
+
Treat this as a 2-day road trip and book the overnight stop before the busiest arrival window.
Day 1
Settle into the route from Clintwood, VA
Aim for roughly 232 miles and 4.5 hours of wheel time on this day.
Day 2
Finish the approach into Chesapeake, VA
Aim for roughly 232 miles and 4.5 hours of wheel time on this day.
Your first comfortable stop window is around 102 miles from Clintwood, VA.
This route usually feels better as a 2-day drive than as one long push.
Plan about 2 real breaks rather than only quick fuel stops.
The longest stretch is on I 81 for about 196.9 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 26
5 decision points cluster between mile 59.8 and 379.1 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
7
59.8 mi into trip|~1h 29m in|US 58 ALT; VA 75 / Cummings Street
At end of road, turn right onto US 58 ALT; VA 75 / Cummings Street
Lane positioning matters here
Use the straight lane.
8
125 mi into trip|~2h 40m in|I 81; US 11
Keep slight left at fork onto I 81; US 11 toward I 81 North, US 11 North: Roanoke
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight lane.
Toward I 81 North, US 11 North: Roanoke
7
265 mi into trip|~5h 15m in|I 64
Keep slight right at fork onto I 64 toward I 64 East: Richmond
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight lane.
Toward I 64 East: Richmond
8
355 mi into trip|~6h 53m in
Take the exit toward I 295 North: Washington, Norfolk
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 177
Toward I 295 North: Washington, Norfolk
8
379.1 mi into trip|~7h 19m in
Take the exit toward I 64 East: Norfolk, Virginia Beach
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 28A
Toward I 64 East: Norfolk, Virginia Beach
Fuel & Cost
Regular Gas
$72.70 one way
$145.40 round trip
$3.97/gal25.4 MPG avg163 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.34
$79.49
$158.98
premium
$4.70
$86.04
$172.09
diesel
$5.61
$102.64
$205.29
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$73
Hotel (1n)
$80–$140
Meals
$50–$100
Total
$203–$313
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 162.7 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $49 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
139.5
1
$48.81
$22.32
Efficient EV
116.2
1
$40.68
$18.60
EV Truck/SUV
186
2
$65.09
$29.75
Gas CO2
163 kg
EV CO2
54 kg (67% less)
Plan for 1 charging stop. A 30-minute DC fast charge mid-route should be enough to complete the trip comfortably.
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 16, 2026
Origin
Clintwood, VA
Night
in Clintwood on Saturday
Local time
9:27 PM
EDT
Current temp
72°F
Unavailable
Live forecast
Destination
Chesapeake, VA
Night
in Chesapeake on Saturday
Local time
9:27 PM
EDT
Current temp
85°F
Unavailable
Live forecast
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.
For long drives, weather on day two can matter just as much as conditions at departure, so check the whole travel window rather than only the first day.
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
13 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
9h 5m on the road
This is long enough that the arrival forecast matters almost as much as departure conditions. Recheck both ends before you roll.
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...
2 mi from route
~5 min detour
Free
near mile 448.9
Park Closure: Road Closure and Fishing Pier Impact
On May 13, 1607, Jamestown was established as the first permanent English settlement in North America. Three cultures came together – European, Virginia Indian and African–to create a new society that...
7 mi from route
~17 min detour
$15
near mile 416.8
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...
20 mi from route
~51 min detour
Free
near mile 192.4
Two hundred ninety-two days, eight offensives, over 70,000 casualties, U. S. Colored Troops, and the decline of Gen. Lee's Army of Northern Virginia all describe the Siege of Petersburg. U.S. forces c...
28 mi from route
~69 min detour
Free
near mile 384.8
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a highway-focused drive, as 82% of your journey takes place on high-speed roads. The character of the trip is defined by a significant 196.9-mile stretch on I-81, which serves as the backbone of your travel. While the interstate segments prioritize efficiency and speed, the transition between these major arteries keeps the drive from feeling entirely monotonous. You will find that the road demands steady attention as you navigate the heavy traffic often associated with these major corridors. Ultimately, the route is designed for getting from point A to point B reliably rather than for winding, low-speed sightseeing.
82% highway — fuel and pacing are the main things to plan.
43 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 196.9 mi on I 81.
How Hard Is This Drive?
9/10
This is a straightforward highway drive that stays mostly on I 81 and I 64. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 59.8 miles in near US 58 ALT; VA 75 / Cummings 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 26 significant decision points across 464.9 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 59.8 miles (US 58 ALT; VA 75 / Cummings Street): Lane positioning matters here; at 125 miles (I 81; US 11): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 265 miles (I 64): Highway fork - watch signs carefully. 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.
Between Clintwood, VA and Chesapeake, VA, road signs point toward Norfolk and Virginia Beach.
Norfolk
355 mi in|~6h 53m
Virginia Beach
379.1 mi in|~7h 19m
Frequently Asked Questions
The longest stretch is about 196.9 miles on I 81. The full list of main roads is in the Roads section above.
Yes — a 2-day pace is more comfortable than one long haul. A sensible stopping point is after roughly 232 miles on day one.
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 2 meaningful breaks. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 59.8 miles (US 58 ALT; VA 75 / Cummings Street): Lane positioning matters here; at 125 miles (I 81; US 11): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 265 miles (I 64): Highway fork - watch signs carefully. Lane positioning matters here.
Yes — Fort Monroe National Monument, Colonial National Historical Park and Booker T Washington National Monument (4 total within detour distance). See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 9.1 hours each way, a round trip means 18.2 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.
