The drive from Chatmoss, VA to Chesapeake, VA covers 224.5 miles and takes about 5h 1m behind the wheel.
This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Southampton Parkway, US 58, Clarksville Bypass for much of the mileage,
and the overall profile is mixed drive.
The longest uninterrupted segment is about 62.1 miles on Southampton Parkway.
At current regular gas prices, budget about $35.11 one way before food or hotel 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
112.3 miles from Chatmoss, VA
A natural place for your longest stop of the day
, about 2h 28m into the drive
.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 5h 1m. Total distance: 224.5 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 1m drive, comfortable solo distance.
Scenic Drive
Mixed drive route profile with national parks nearby.
Drive Character
The drive from Chatmoss, VA to Chesapeake, VA covers 224.5 miles and takes about 5h 1m, using a mix of highways and local roads.
Expect a mix of faster highway mileage and slower local approaches near the beginning or end.
There are about 38 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Southampton Parkway is the longest continuous segment at about 62.1 miles.
How Hard Is This Drive?
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 4.7 miles in near US 58.
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 20 significant decision points across 224.5 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 4.7 miles (US 58): Highway fork - watch signs carefully. Lane positioning matters here; at 33.8 miles (US 58; US 360 / South Boston Road): Merge point - match speed before joining. Lane positioning matters here; at 84.1 miles (US 58 / Clarksville Bypass): Highway fork - watch signs carefully. Multiple destination signs - pick the right one.
Critical Maneuvers
5 of 20 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
7
4.7 mi into trip|~7m 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
33.8 mi into trip|~44m 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.
6
84.1 mi into trip|~1h 50m 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
8
219.9 mi into trip|~4h 52m 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
220.1 mi into trip|~4h 53m 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
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 Chatmoss, VA to Chesapeake, VA, road signs begin pointing toward Hill along the way.
Hill
84.1 mi in|~1h 50m|via US 58
Main Roads
Road
Distance
Duration
Southampton Parkway
62.1 mi
1h 20m
US 58
29.1 mi
36m
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
Pleasant Shade Drive
6.4 mi
8m
South Boston Highway
5.3 mi
7m
Longest stretch:
Southampton Parkway
— 62.1 mi, about 1h 20m
Turn-by-Turn Driving Directions
Step-by-step road directions between Chatmoss, VA and Chesapeake, VA.
1
Start on SR 777
250 ft·8 sec·Mount Olivet Road
2
Turn right onto SR 620
0.7 mi·1 min·Old Liberty Drive
3
At end of road, turn left onto SR 650
0.7 mi·1 min·Irisburg Road
4
Turn left
0.3 mi·42 sec
Toward US 58 East
5
Merge onto US 58
2.9 mi·3 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
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 112.3 miles from Chatmoss, VA, or about 2h 28m 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 49 miles or 1h 5m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 112.3 miles or 2h 28m 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 4m
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 Chatmoss, 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 Chatmoss, VA
This is one driving day of about 224.5 miles and 5h 1m.
Your first comfortable stop window is around 49 miles from Chatmoss, 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.
Halfway Point
Midpoint
About 112.3 mi from Chatmoss, VA
· 2h 28m into the drive
The midpoint is around 112.3 miles from Chatmoss, VA, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel check
Top up before Southampton Parkway if your tank is already low. That segment runs about 62.1 miles.
Arriving in Chesapeake, VA
The final approach into Chesapeake, VA usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Chesapeake, VA.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
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 224.5
Park Closure: Road Closure and Fishing Pier Impact
Station data from NREL Alternative Fuel Stations database.
Driving Electric?
About $24 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
67.4
0
$23.57
$10.78
Efficient EV
56.1
0
$19.64
$8.98
EV Truck/SUV
89.8
1
$31.43
$14.37
Gas CO2
79 kg
EV CO2
26 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 Apr 17, 2026
Origin
Chatmoss, VA
Late night
in Chatmoss on Friday
Local time
5:02 AM
EDT
Current temp
46°F
Unavailable
Live forecast
Destination
Chesapeake, VA
Late night
in Chesapeake on Friday
Local time
5:02 AM
EDT
Current temp
68°F
Mostly Clear
SW 7 to 10 mph3% chanceLive forecast
81°F
Lawrenceville, VA
112 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
22 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 1m 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.
Frequently Asked Questions
The drive from Chatmoss, VA to Chesapeake, VA covers 224.5 miles and takes about 5h 1m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Southampton Parkway, US 58, Clarksville Bypass. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 112.3 miles from Chatmoss, VA. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $35.11 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
An early start around 7-8 AM gets you there with plenty of daylight left. A late afternoon start means arriving after dark. Morning is better.
Plan about 1 meaningful break for fuel, food, or rest. Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
This is a demanding drive. With 20 significant decision points across 224.5 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.
The main spots that need attention: at 4.7 miles (US 58): Highway fork - watch signs carefully. Lane positioning matters here; at 33.8 miles (US 58; US 360 / South Boston Road): Merge point - match speed before joining. Lane positioning matters here; at 84.1 miles (US 58 / Clarksville Bypass): Highway fork - watch signs carefully. Multiple destination signs - pick the right one.
On the drive from Chatmoss, VA to Chesapeake, VA, road signs begin pointing toward Hill along the way.
How this page is built
Compiled and maintained by the Trip.ovh planning team at COD Solutions Oy (Helsinki). Each route is built from authoritative open government and mapping datasets rather than crowdsourced reviews. Distances and geometry come from
OSRM
over
OpenStreetMap.
Fuel cost uses
EIA
weekly regional averages.
EV charging comes from the
NREL Alternative Fuels
dataset.
National park proximity is from the
NPS API.
Pages are published only after passing our data-quality checks; our
methodology page
documents refresh cadence, editorial standards, and known limitations.
