Chesapeake, VA to Matoaca, VA is 90.7 miles and takes about 2h 2m via James River Drive and Colonial Trail West, with a fuel budget near $14 and enough daylight to finish in a day. This trip stays within Virginia, traversing the Southeast region. Given its relatively short distance and primarily surface road profile, this route is well-suited for a single-day excursion. You'll find it offers a straightforward drive with minimal highway time, making it an accessible option for a quick trip between these two Virginia locations.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
45.4 miles from Chesapeake, VA
A natural place for your longest stop of the day
, about 1h 3m into the drive
.
Main Roads
Road
Distance
Duration
James River Drive
14.6 mi
19m
Colonial Trail West
13.3 mi
15m
Benns Church Boulevard
12.1 mi
15m
Colonial Trail East
9.9 mi
11m
Western Freeway
7.4 mi
9m
Bridge Road
6.5 mi
11m
East Washington Street
4 mi
4m
River Road
2.9 mi
4m
Longest stretch:
James River Drive
— 14.6 mi, about 19m
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake, VA and Matoaca, 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
1.9 mi·3 min·I 264; US 460 ALT
8
Take the exit
0.4 mi·37 sec
Exit 6Toward VA 164 West: Martin Luther King Jr Expressway, NorfolkUse the straight / slight right lanes.
9
Continue on VA 164
0.5 mi·48 sec·Martin Luther King Jr Freeway
Use the straight / slight right lanes.
10
Continue on US 58; VA 164
0.6 mi·55 sec·Martin Luther King Freeway
11
Continue on VA 164
7.4 mi·9 min·Western Freeway
Use the straight / slight right lanes.
12
Continue on US 17
6.5 mi·11 min·Bridge Road
Use the straight lane.
13
Continue on US 17
2.4 mi·3 min·Carrollton Boulevard
14
Turn left onto Brewers Neck Boulevard
2.9 mi·4 min·Brewers Neck Boulevard
15
Merge onto US 258; VA 10
12 mi·15 min·Benns Church Boulevard
16
Continue on VA 10
9.9 mi·11 min·Colonial Trail East
17
Turn left onto VA 10; VA 31
1.0 mi·1 min·Rolfe Highway
18
Turn right onto VA 10
13 mi·15 min·Colonial Trail West
19
Continue on VA 10
15 mi·19 min·James River Drive
20
Continue on VA 10; VA 156 BUS
1.2 mi·2 min·East Randolph Road
21
Turn left onto VA 156 Business
1.8 mi·2 min·Winston Churchill Drive
22
Continue on VA 36
0.4 mi·26 sec·Oaklawn Boulevard
23
Continue on VA 36
1.0 mi·1 min·Woodlawn Street
24
Continue on VA 36
1.0 mi·1 min·Oaklawn Boulevard
25
Continue on VA 36
4.0 mi·4 min·East Washington Street
26
Turn right onto US 301; VA 36
0.3 mi·34 sec·North Crater Road
Use the right lane.
27
At end of road, turn left onto US 301; VA 36
0.6 mi·59 sec·Bollingbrook Street
Use the straight / left lanes.
28
At end of road, turn right onto VA 36
225 ft·12 sec·North Sycamore Street
Use the right lane.
29
Turn left onto VA 36
0.1 mi·13 sec·West Old Street
30
Continue on VA 36
0.5 mi·57 sec·Grove Avenue
31
At end of road, turn right onto VA 36
0.1 mi·14 sec·Fleet Street
32
Continue on VA 36
0.8 mi·1 min·Chesterfield Avenue
33
Continue on VA 36
2.9 mi·4 min·River Road
34
Turn left onto SR 1304
163 ft·8 sec·Wilcox Street
35
Turn right onto Fitzhugh Street
287 ft·12 sec·Fitzhugh Street
36
Arrive at destination
Fitzhugh Street
Trip Plan
With a total duration of just over 2 hours, this is a very manageable drive that you can easily complete in one day. Leaving Chesapeake in the morning will give you plenty of time to reach Matoaca with flexibility for any unexpected delays. The fuel cost is estimated at $14, so ensure your tank is adequately filled before you depart. Given the route's profile, which is mostly surface roads, pay attention to local speed limits and traffic signals. The longest continuous stretch without a turn or change in road designation is 14.6 miles on James River Drive, so be mindful of that segment.
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 45.4 miles from Chesapeake, VA, or about 1h 3m into the drive.
The longest continuous stretch on this route runs about 14.6 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 20 miles or 30m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 45.4 miles or 1h 3m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 39m
Traffic, exits, and arrival timing usually matter more near Matoaca, 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 90.7 miles and 2h 2m.
Your first comfortable stop window is around 20 miles from Chesapeake, VA.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on James River Drive for about 14.6 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 18
5 decision points cluster between mile 1.8 and 86.1 — 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
4.3 mi into trip|~7m in
Take the exit toward VA 164 West: Martin Luther King Jr Expressway, Norfolk
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 6
Toward VA 164 West: Martin Luther King Jr Expre...
7
85.5 mi into trip|~1h 54m in|US 301; VA 36 / Bollingbrook Street
At end of road, turn left onto US 301; VA 36 / Bollingbrook Street
Lane positioning matters here
Use the straight / left lanes.
7
86.1 mi into trip|~1h 55m in|VA 36 / North Sycamore Street
At end of road, turn right onto VA 36 / North Sycamore Street
Lane positioning matters here
Use the right lane.
Fuel & Cost
Regular Gas
$13.90 one way
$27.80 round trip
$3.89/gal25.4 MPG avg32 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.27
$15.25
$30.50
premium
$4.64
$16.56
$33.12
diesel
$5.60
$19.99
$39.99
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$14
Meals
$25–$50
Total
$39–$64
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 31.7 kg one way.
Prices: EIA weekly data, 2026-08-31.
Driving Electric?
About $10 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
27.2
0
$9.52
$4.35
Efficient EV
22.7
0
$7.94
$3.63
EV Truck/SUV
36.3
0
$12.70
$5.80
Gas CO2
32 kg
EV CO2
11 kg (66% less)
This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.
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 Aug 21, 2026
Origin
Chesapeake, VA
Late night
in Chesapeake on Friday
Local time
2:55 AM
EDT
Current temp
74°F
Chance Showers And Thunderstorms then Showers And Thunderstorms Likely
SW 3 to 7 mph61% chanceLive forecast
Destination
Matoaca, VA
Late night
in Matoaca on Friday
Local time
2:55 AM
EDT
Current temp
69°F
Chance Showers And Thunderstorms
N 3 mph54% chanceLive 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.
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
5 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
2h 2m on the road
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
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.
Petersburg National Battlefield
National Battlefield
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...
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...
10 mi from route
~26 min detour
$15
near mile 40.7
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...
11 mi from route
~27 min detour
Free
near mile 9.4
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This drive is mostly surface roads, with only 13% on highways. You'll encounter a longest stretch of 14.6 miles on James River Drive. Expect to transition away from highway cruising relatively early in your trip. The route will primarily feature surface roads, so plan for typical speeds and traffic patterns associated with non-highway travel.
Only 13% highway — the rest is turn-by-turn surface driving.
36 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 14.6 mi on James River Drive.
How Hard Is This Drive?
8/10
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. 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 Effort8/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This is a demanding drive. With 18 significant decision points across 90.7 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 4.3 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
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 2h 2m. Total distance: 90.7 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
2h 2m drive, comfortable solo distance.
Scenic Drive
Mostly surface roads route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 14.6 miles on James River Drive. The full list of main roads is in the Roads section above.
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 Matoaca, 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. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
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 4.3 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — Petersburg National Battlefield, Colonial National Historical Park and Fort Monroe National Monument. See the National Parks section for detour distances and tips on detours.
Yes. A round trip is manageable in a single day if you plan a break at Matoaca, VA before heading back.
