Chesapeake, VA to Hillsville, VA is 290.5 miles and takes about 6h 26m via US 58, with a fuel budget near $45 and enough daylight to finish in a day. This trip stays within Virginia, moving from the Southeast region to the Southeast region. Expect a mixed highway and surface road experience, making it a solid option for a single-day drive. Consider this route if you're looking for a straightforward trip without extensive planning, keeping your budget in mind for the estimated $45 in fuel 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
145.2 miles from Chesapeake, VA
A natural place for your longest stop of the day
, about 3h 15m into the drive
.
Main Roads
Road
Distance
Duration
US 58
81 mi
1h 46m
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
Danville Expressway
13.9 mi
16m
I 264
6.7 mi
9m
Pleasant Shade Drive
6.3 mi
8m
Longest stretch:
US 58
— 81 mi, about 1h 46m
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 Hillsville, 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
Take the exit onto US 58
10 mi·12 min·US 58
Toward US 58 West: Stuart, Roanoke
32
Take the exit onto US 58
55 mi·1 hr 13 min·US 58
Toward US 58 West: Stuart
33
Continue on US 58
2.2 mi·2 min·Hillsville Bypass
34
Take the exit
0.2 mi·33 sec
Toward US 52: Fancy Gap, HillsvilleUse the slight right lane.
35
Turn right onto US 52
1.3 mi·2 min·South Main Street
Use the right lane.
36
Turn left onto US 221; US 58 BUS
73 ft·2 sec·West Stuart Drive
37
Arrive at destination
US 221; US 58 BUS
Trip Plan
This is a feasible one-day trip, so you have flexibility on when to depart. Leaving in the morning will give you ample daylight to complete the 290.5 miles. Plan for at least one stop to break up the 6h 26m drive time. Given the longest stretch is 81 miles on US 58, consider a fuel stop before or after this segment to ensure you're topped up. Keep an eye on your fuel gauge as you approach Hillsville, with an estimated fuel cost of $45.
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.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 145.2 miles from Chesapeake, VA, or about 3h 15m into the drive.
The longest continuous stretch on this route runs about 81 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 64 miles or 1h 26m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 145.2 miles or 3h 15m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 5h 16m
Traffic, exits, and arrival timing usually matter more near Hillsville, 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 290.5 miles and 6h 26m.
Your first comfortable stop window is around 64 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 US 58 for about 81 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 1.8 and 289 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
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...
7
289 mi into trip|~6h 23m in
Take the exit toward US 52: Fancy Gap, Hillsville
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Toward US 52: Fancy Gap, Hillsville
Fuel & Cost
Regular Gas
$42.89 one way
$85.78 round trip
$3.75/gal25.4 MPG avg102 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.12
$47.13
$94.26
premium
$4.49
$51.38
$102.75
diesel
$4.80
$54.85
$109.70
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$43
Meals
$25–$50
Total
$68–$93
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 101.6 kg one way.
Prices: EIA weekly data, 2026-07-13.
Driving Electric?
About $31 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
87.2
1
$30.50
$13.94
Efficient EV
72.6
0
$25.42
$11.62
EV Truck/SUV
116.2
1
$40.67
$18.59
Gas CO2
102 kg
EV CO2
34 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 Jul 17, 2026
Origin
Chesapeake, VA
Late night
in Chesapeake on Sunday
Local time
3:00 AM
EDT
Current temp
76°F
Areas Of Smoke
SE 3 to 7 mph1% chanceLive forecast
Destination
Hillsville, VA
Late night
in Hillsville on Sunday
Local time
3:00 AM
EDT
Current temp
68°F
Patchy Smoke
S 3 mph7% chanceLive forecast
86°F
South Boston, VA
145 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
8 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
6h 26m on the road
Start early — leave by 6-7 AM to arrive at a reasonable hour.
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
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
You'll spend about 58% of this 290.5-mile drive on highways. The longest continuous stretch on a highway is 81 miles on US 58. The route transitions between highway driving and surface roads, so be prepared for a change in pace. Expect periods of rural cruising mixed with areas that have more frequent exits and potential for urban merging.
58% highway, the rest on surface roads — varied driving throughout.
37 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 81 mi on US 58.
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 1.8 miles in.
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 290.5 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 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; at 9.2 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Elevation Profile
Hilly terrain with moderate elevation changes
2,933 ft-1 ft
Total Climb
3,002 ft
Total Descent
502 ft
Highest Point
2,933 ft
~269.7 mi in
Elevation Range
2,933 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 Hillsville, VA, road signs point toward Danville, Martinsville and Roanoke.
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 6h 26m. Total distance: 290.5 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
6h 26m drive, plan rest stops for pacing.
Scenic Drive
Mixed highway & surface route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 81 miles on US 58. 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 Hillsville, 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 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; at 9.2 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — Fort Monroe National Monument. See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 6.4 hours each way, a round trip means 12.9 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Hillsville, VA before the return drive.
