Chesapeake, VA to Middletown, VA is 224.2 miles and takes about 4h 37m via I 64, I 95, and Warrenton Road, with a fuel budget near $35 and enough daylight to finish in a day. This trip stays within Virginia, moving from the Southeast region to another part of the Southeast. Expect a mostly highway profile for the majority of your drive. This route is a solid choice if you're looking for a straightforward, single-day trip without excessive driving time. It's a practical option for getting from the Tidewater area to the northern part of the state.
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
112.1 miles from Chesapeake, VA
A natural place for your longest stop of the day
, about 2h 16m into the drive
.
Main Roads
Road
Distance
Duration
I 64
61.1 mi
1h 7m
I 95
47.3 mi
51m
Warrenton Road
22.9 mi
33m
US 17
18.6 mi
20m
Korean War Veterans Memorial Highway
11.9 mi
12m
James Madison Highway
11.3 mi
15m
Hampton Roads Beltway
9.6 mi
12m
I 66
9.6 mi
10m
Longest stretch:
I 64
— 61.1 mi, about 1h 7m
Traffic on I-295
Hour-of-day weekday pattern from 34 FHWA count stations on your route.
Peak
4 PM
~2,876 veh/hr typical
· worst 3,445
Quietest
2 AM
~163 veh/hr
Peak-to-quiet ratio
17.6×
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 Middletown, 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 left at fork
0.7 mi·1 min
Exit 6BToward I 264 East: Waterside Drive, Saint Paul Boulevard, Downtown, NorfolkUse the slight left lane.
6
Keep slight left at fork onto US 460 ALT
0.2 mi·26 sec·US 460 ALT
Exit 9Toward Waterside Drive, St Paul's BoulevardUse the slight left lane.
7
Keep slight left at fork onto US 460 ALT
0.3 mi·53 sec·US 460 ALT
Toward Saint Paul's BoulevardUse the straight / slight right lanes.
8
Turn right onto US 460 ALT
0.6 mi·1 min·Saint Pauls Boulevard
Use the straight / right lanes.
9
Continue on US 460
1.2 mi·2 min·Monticello Avenue
10
Turn left onto US 460
486 ft·13 sec·Church Street
11
Continue on US 460
4.0 mi·9 min·Granby Street
Use the left lane.
12
Turn left
0.2 mi·26 sec
Toward I 64
13
Merge onto I 64
3.8 mi·5 min·Hampton Roads Beltway
Use the straight / slight right lanes.
14
Continue on I 64; US 60
3.5 mi·4 min·Hampton Roads Bridge-Tunnel
15
Continue on I 64; US 60
5.9 mi·7 min·Hampton Roads Beltway
Use the straight / slight right lanes.
16
Keep slight left at fork onto I 64
61 mi·1 hr 7 min·I 64
Use the straight / slight right lanes.
17
Take the exit
0.5 mi·32 sec
Exit 200Toward I 295, US 60: Washington, Rocky Mount NCUse the straight / slight right lanes.
18
Keep slight right at fork
1.3 mi·2 min
Toward I 295 North: WashingtonUse the straight / slight right lanes.
19
Merge onto I 295
12 mi·12 min·Korean War Veterans Memorial Highway
20
Take the exit
2.4 mi·2 min
Exit 43AToward I 95 North: WashingtonUse the slight left lane.
21
Merge onto I 95
46 mi·49 min·I 95
Use the straight / slight right lanes.
22
Keep slight right at fork onto I 95; US 17
1.6 mi·1 min·I 95; US 17
23
Keep slight right at fork
0.3 mi·41 sec
Toward US 17 Business: Falmouth
24
Turn left onto US 17
23 mi·33 min·Warrenton Road
Use the straight lane.
25
Continue on US 17
4.2 mi·7 min·Marsh Road
26
Turn right onto US 15; US 29
4.6 mi·6 min·James Madison Highway
27
Continue on US 15; US 17; US 29
2.4 mi·3 min·Eastern Bypass
28
Keep slight right at fork onto US 17
2.3 mi·3 min·Eastern Bypass
Toward US 17 North
29
Continue on US 17
6.7 mi·9 min·James Madison Highway
30
Continue on US 17
2.7 mi·3 min·Winchester Road
31
Turn left onto US 17
19 mi·20 min·US 17
Use the left lane.
32
Continue on I 66
9.6 mi·10 min·I 66
33
Keep slight right at fork
0.7 mi·1 min
Exit 1BToward I 81 North: WinchesterUse the slight right lane.
34
Merge onto I 81
1.2 mi·1 min·I 81
Toward I 81 North: Winchester
35
Take the exit
0.2 mi·30 sec
Exit 302Toward SR 627: MiddletownUse the slight right lane.
36
Turn left onto SR 627
0.5 mi·1 min·Reliance Road
37
At end of road, turn left onto US 11
0.6 mi·1 min·Main Street
38
Arrive at destination
US 11
Trip Plan
Given the 4h 37m estimated drive time, starting in the morning allows ample time to reach Middletown, VA, on the same day. With only one recommended stop and a manageable fuel cost of around $35, you can be flexible with your timing. Keep an eye on traffic, especially around the I 95 corridor, as it can impact your duration. Consider stopping for fuel before leaving the major interstate sections to ensure you have plenty for the final stretch on Warrenton Road.
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 112.1 miles from Chesapeake, VA, or about 2h 16m into the drive.
The longest continuous stretch on this route runs about 61.1 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 112.1 miles or 2h 16m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 3h 48m
Traffic, exits, and arrival timing usually matter more near Middletown, 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 224.2 miles and 4h 37m.
Your first comfortable stop window is around 49 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 I 64 for about 61.1 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 26
5 decision points cluster between mile 1.8 and 221 — 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 left at fork toward I 264 East: Waterside Drive, Saint Paul Boulevard, Downtown, Norfolk
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left lane.
Exit 6B
Toward I 264 East: Waterside Drive, Saint Paul...
9
2.5 mi into trip|~3m in|US 460 ALT
Keep slight left at fork onto US 460 ALT toward Waterside Drive, St Paul's Boulevard
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left lane.
Exit 9
Toward Waterside Drive, St Paul's Boulevard
8
2.7 mi into trip|~4m in|US 460 ALT
Keep slight left at fork onto US 460 ALT toward Saint Paul's Boulevard
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Toward Saint Paul's Boulevard
8
83.3 mi into trip|~1h 43m in
Take the exit toward I 295, US 60: Washington, Rocky Mount NC
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 200
Toward I 295, US 60: Washington, Rocky Mount NC
8
221 mi into trip|~4h 31m in
Keep slight right at fork toward I 81 North: Winchester
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Exit 1B
Toward I 81 North: Winchester
Fuel & Cost
Regular Gas
$35.66 one way
$71.32 round trip
$4.04/gal25.4 MPG avg78 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.41
$38.88
$77.76
premium
$4.78
$42.18
$84.37
diesel
$5.35
$47.22
$94.45
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$36
Meals
$25–$50
Total
$61–$86
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 78.4 kg one way.
Prices: EIA weekly data, 2026-06-01.
Driving Electric?
About $24 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
67.3
0
$23.54
$10.76
Efficient EV
56.1
0
$19.62
$8.97
EV Truck/SUV
89.7
1
$31.39
$14.35
Gas CO2
78 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 Jun 1, 2026
Origin
Chesapeake, VA
Afternoon
in Chesapeake on Wednesday
Local time
2:58 PM
EDT
Current temp
61°F
Partly Cloudy
SW 9 mph0% chanceLive forecast
Destination
Middletown, VA
Afternoon
in Middletown on Wednesday
Local time
2:58 PM
EDT
Current temp
52°F
Partly Cloudy
W 2 mph0% chanceLive forecast
82°F
Bowling Green, 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
9 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
4h 37m 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.
Colonial National Historical Park
National Historical Park
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...
1 mi from route
~4 min detour
$15
near mile 38.6
Park Closure: Jamestown Island Loop Drive to Temporarily Close to Vehicles
Park Closure: Rehabilitation of Colonial Parkway Continues
Cedar Creek & Belle Grove National Historical Park
National Historical Park
Virginia’s Shenandoah Valley has a long and rich heritage that still inspires today. Native Americans first shaped the land, followed by colonists and settlers. The fertile valley became an important...
2 mi from route
~5 min detour
Free
near mile 224.2
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...
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...
The Potomac River corridor is rich in both history and recreation, offering a chance to both explore your heritage and choose your adventure along the way. Start your journey here!
27 mi from route
~67 min detour
Free
near mile 193.2
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 62% of this 224.2-mile drive on highways. The longest continuous stretch without a major change in road type is 61.1 miles on I 64. After the highway segments, you'll transition to Warrenton Road for the remainder of your trip. Expect a mix of high-speed cruising and potentially more local traffic as you approach your destination.
62% highway — fuel and pacing are the main things to plan.
38 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 61.1 mi on I 64.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on I 64 and I 95. 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 26 significant decision points across 224.2 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 2.5 miles (US 460 ALT): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 2.7 miles (US 460 ALT): Highway fork - watch signs carefully. Lane positioning matters here.
Elevation Profile
Mostly flat terrain
839 ft-4 ft
Total Climb
863 ft
Total Descent
155 ft
Highest Point
839 ft
~208.2 mi in
Elevation Range
843 ft
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 Chesapeake, VA to Middletown, VA, road signs begin pointing toward Rocky Mount along the way.
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 4h 37m. Total distance: 224.2 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
4h 37m drive, comfortable solo distance.
Frequently Asked Questions
The longest stretch is about 61.1 miles on I 64. The full list of main roads is in the Roads section above.
Yes — we found about 14 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 Middletown, 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 14 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 2.5 miles (US 460 ALT): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 2.7 miles (US 460 ALT): Highway fork - watch signs carefully. Lane positioning matters here.
Yes — Colonial National Historical Park, Cedar Creek & Belle Grove National Historical Park and Fort Monroe National Monument (5 total within detour distance). See the National Parks section for detour distances and tips on detours.
Possible but tiring. At 4.6 hours each way, an in-and-out day trip would put you behind the wheel for 9.2 hours — manageable with a long break at Middletown, VA, but most travelers stay overnight.
