Origin
Woodstock, VA
Morning in Woodstock on Sunday
Local time
10:18 AM
EDT
Current temp
71°F
Unavailable
Live forecast
Trip from Woodstock, VA to Chesapeake, VA
Compiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Apr 19, 2026 · Editorial standards
Drive Time
4h 55m
Distance
239.4 mi
385 km
Drive Score
9/10
Great drive
Same Day?
Yes, doable
Fuel Cost
$37
one way
EV Charging
Unknown
Best Time to Leave
4 AM
4h 42m
★
6 AM
4h 56m
8 AM
5h 23m
10 AM
5h 5m
12 PM
5h 2m
3 PM
5h 6m
5 PM
5h 21m
8 PM
4h 47m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Woodstock, VA
Bárbara Oliveira
Chesapeake, VA
Wikimedia Commons
Trip Overview
This 239.4-mile drive from Woodstock, VA to Chesapeake, VA is a straightforward trip within the Southeast region, taking approximately 4 hours and 55 minutes. Designed as a single-day journey, it's manageable without an overnight stop, and you can expect a fuel cost of around $37. The route is primarily highway-focused, making it an efficient way to travel between these two Virginia locations. You'll spend most of your time on interstates, so pack your favorite road trip playlist. This drive offers a practical approach to covering ground efficiently.
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
119.7 miles from Woodstock, VA
A natural place for your longest stop of the day , about 2h 32m into the drive .
Main Roads
| Road | Distance | Duration |
|---|---|---|
| US 17 | 75 mi | 1h 33m |
| I 64 | 66.8 mi | 1h 15m |
| I 66 | 28.1 mi | 30m |
| Korean War Veterans Memorial Highway | 13 mi | 14m |
| James Madison Highway | 11.6 mi | 16m |
| I 81 | 8.6 mi | 9m |
| Hampton Roads Beltway | 6.8 mi | 8m |
| Eastern Bypass | 4.9 mi | 6m |
Longest stretch:
US 17
— 75 mi, about 1h 33m
Turn-by-Turn Driving Directions
Step-by-step road directions between Woodstock, VA and Chesapeake, VA.
1
Start on West Court Street
116 ft
·
12 sec
·
West Court Street
2
Turn left onto US 11
1.0 mi
·
3 min
·
North Main Street
3
Continue on US 11
4.4 mi
·
6 min
·
Old Valley Pike
4
Continue on US 11
0.8 mi
·
1 min
·
Main Street
5
Continue on US 11
0.5 mi
·
56 sec
·
Old Valley Pike
6
Turn left onto SR 651
0.8 mi
·
1 min
·
Mount Olive Road
7
Take the ramp
0.3 mi
·
32 sec
Use the right lane.
8
Merge onto I 81
8.6 mi
·
9 min
·
I 81
9
Take the exit
0.4 mi
·
47 sec
Toward I 66 East: Front Royal, Washington
10
Continue on I 66
28 mi
·
30 min
·
I 66
11
Take the exit onto US 17
0.3 mi
·
32 sec
·
US 17
Toward US 17: Warrenton, Fredericksburg
12
Keep slight right at fork onto US 17
0.1 mi
·
13 sec
·
US 17
13
Merge onto US 17
2.4 mi
·
3 min
·
Winchester Road
14
Continue on US 17
6.5 mi
·
8 min
·
James Madison Highway
15
Keep slight right at fork onto US 17
4.9 mi
·
6 min
·
Eastern Bypass
Toward US 17 South: Fredericksburg
Use the straight / slight right lanes.
16
Continue on US 15; US 17; US 29
5.1 mi
·
7 min
·
James Madison Highway
17
Keep slight right at fork onto US 17
27 mi
·
39 min
·
US 17
Toward US 17 South
18
Take the exit onto US 17
48 mi
·
53 min
·
US 17
Toward I 95 South, US 17 South: Richmond
Use the straight / slight right lanes.
19
Take the exit
1.9 mi
·
2 min
Exit 84A
Toward I 295 South: Williamsburg, Norfolk, Va Beach
Use the slight left / straight lanes.
20
Merge onto I 295
13 mi
·
14 min
·
Korean War Veterans Memorial Highway
Use the straight / slight right lanes.
21
Take the exit
1.3 mi
·
2 min
Exit 28A
Toward I 64 East: Norfolk, Virginia Beach
Use the straight / slight right lanes.
22
Merge onto I 64
67 mi
·
1 hr 15 min
·
I 64
Use the straight / slight right lanes.
23
Keep slight left at fork onto I 64; US 60
342 ft
·
5 sec
·
Hampton Roads Beltway
24
Continue on I 64; US 60
3.5 mi
·
4 min
·
Hampton Roads Bridge-Tunnel
25
Continue on I 64; US 60
6.7 mi
·
8 min
·
Hampton Roads Beltway
Use the straight / slight right lanes.
26
Take the exit
0.2 mi
·
32 sec
Exit 278
Toward VA 194 South: Chesapeake Boulevard
Use the slight right lane.
27
Turn straight onto VA 194
2.1 mi
·
3 min
·
Chesapeake Boulevard
Use the left lane.
28
Turn straight
135 ft
·
7 sec
29
Turn left onto VA 247
1.1 mi
·
1 min
·
Ballentine Boulevard
30
Turn right onto VA 166
0.9 mi
·
1 min
·
East Princess Anne Road
31
Turn left onto VA 166
0.6 mi
·
1 min
·
Park Avenue
32
Turn left onto US 460; VA 166; VA 168
0.3 mi
·
57 sec
·
East Brambleton Avenue
Use the left / straight / right lanes.
33
Continue on US 460; VA 166; VA 168
0.7 mi
·
1 min
·
Campostella Road
34
Turn right onto US 460; VA 166
0.7 mi
·
1 min
·
Wilson Road
Use the right lane.
35
Continue on US 460; VA 166
0.3 mi
·
27 sec
·
22nd Street
36
Continue on US 460; VA 166
0.3 mi
·
29 sec
·
Poindexter Street
Use the straight lane.
37
Turn right onto D Street
412 ft
·
18 sec
·
D Street
38
Arrive at destination
D Street
Trip Plan
Given its 4 hour and 55-minute duration, departing Woodstock, VA in the morning is your best bet to arrive in Chesapeake with ample daylight. While only one planned stop is suggested, the 75-mile stretch on US 17 means you'll want to ensure your fuel tank is sufficiently full before embarking on that segment. Plan to refuel if you see a good opportunity before hitting that longer stretch. The drive is efficient enough that you have flexibility in when and where you take breaks, but keeping an eye on your gas gauge is key for this highway-focused itinerary.
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 119.7 miles from Woodstock, VA, or about 2h 32m into the drive.
The longest continuous stretch on this route runs about 75 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 53 miles or 1h 5m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 119.7 miles or 2h 32m 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 59m
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 Woodstock, 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 Woodstock, VA
This is one driving day of about 239.4 miles and 4h 55m.
Your first comfortable stop window is around 53 miles from Woodstock, 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 17 for about 75 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Mid-route town
Meal stop
120 mi into the route
Best for: Lunch, fuel, and a longer reset
This sits close to the middle of the route, so it works well for the longest stop of the day.
Pacing Suggestions
Fuel and coffee
A short stop after about 53 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 119.7 miles from Woodstock, VA, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel checkTop up before US 17 if your tank is already low. That segment runs about 75 miles.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Heads-up: tricky spots
5 of 255 decision points cluster between mile 53.9 and 232 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
7
53.9 mi into trip
|
~1h 7m in
|
US 17 / Eastern Bypass
Keep slight right at fork onto US 17 / Eastern Bypass toward US 17 South: Fredericksburg
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Toward US 17 South: Fredericksburg
7
90.7 mi into trip
|
~2h in
|
US 17
Take the exit onto US 17 toward I 95 South, US 17 South: Richmond
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.
Toward I 95 South, US 17 South: Richmond
8
138.7 mi into trip
|
~2h 53m in
Take the exit toward I 295 South: Williamsburg, Norfolk, Va Beach
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left / straight lanes.
Exit 84A
Toward I 295 South: Williamsburg, Norfolk, Va B...
8
153.5 mi into trip
|
~3h 9m 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
7
232 mi into trip
|
~4h 41m in
Take the exit toward VA 194 South: Chesapeake Boulevard
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight right lane.
Exit 278
Toward VA 194 South: Chesapeake Boulevard
Fuel & Cost
Regular Gas
$37.44 one way
$74.87 round trip
$3.97/gal
25.4 MPG avg
84 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.34 | $40.93 | $81.87 |
| premium | $4.70 | $44.31 | $88.62 |
| diesel | $5.61 | $52.86 | $105.71 |
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$37
Meals
$25–$50
Total
$62–$87
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 83.8 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $25 in charging · 0 stops · 67% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 71.8 | 0 | $25.14 | $11.49 |
| Efficient EV | 59.9 | 0 | $20.95 | $9.58 |
| EV Truck/SUV | 95.8 | 1 | $33.52 | $15.32 |
Gas CO2
84 kg
EV CO2
28 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.
Destination
Chesapeake, VA
Morning in Chesapeake on Sunday
Local time
10:18 AM
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.
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
14 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
4h 55m 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...
0 mi from route
$15
near mile 198.1
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...
1 mi from route
~1 min detour
Free
near mile 16.5
View on nps.gov
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
~4 min detour
Free
near mile 222.8
View on nps.gov
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...
26 mi from route
~66 min detour
Free
near mile 156.8
View on nps.gov
Shenandoah National Park
National Park
Just 75 miles from the bustle of Washington, D.C., Shenandoah National Park is a land bursting with cascading waterfalls, spectacular vistas, fields of wildflowers, and quiet wooded hollows. With over...
27 mi from route
~67 min detour
$30
View on nps.gov
Potomac Heritage National Scenic Trail
National Scenic Trail
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!
28 mi from route
~70 min detour
Free
near mile 41.3
View on nps.gov
Park data from the National Park Service API. Alerts update every 2 hours.
What kind of drive is this?
The majority of this 75% highway drive consists of interstate travel, promising relatively fast and consistent speeds. You'll navigate using US 17 and I-64, with I-66 also playing a part in connecting the segments. The longest uninterrupted stretch covers 75 miles on US 17, so be prepared for a significant period without needing to exit. While largely a highway experience, the transition between these major arteries will define the character of your time behind the wheel. Expect a steady pace for most of the journey.
75% 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: 75 mi on US 17.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on US 17 and I 64. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 53.9 miles in near US 17 / Eastern Bypass.
Driving Effort
10/10
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 25 significant decision points across 239.4 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 53.9 miles (US 17 / Eastern Bypass): Highway fork - watch signs carefully. Lane positioning matters here; at 90.7 miles (US 17): Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 138.7 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Woodstock, VA and Chesapeake, VA, road signs point toward Washington, Fredericksburg, Norfolk, Va Beach and Virginia Beach.
Washington
16.2 mi in
|
~23m
Fredericksburg
44.7 mi in
|
~54m
|
via US 17
Norfolk
138.7 mi in
|
~2h 53m
Va Beach
138.7 mi in
|
~2h 53m
Virginia Beach
153.5 mi in
|
~3h 9m
About the Cities
Arriving in Chesapeake, VA
Full guide →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.
City content from Wikivoyage (CC BY-SA 4.0) and Wikidata (CC0).
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 4h 55m. Total distance: 239.4 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
4h 55m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (75%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 75 miles on US 17. The full list of main roads is in the Roads section above.
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 1 meaningful breaks. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 53.9 miles (US 17 / Eastern Bypass): Highway fork - watch signs carefully. Lane positioning matters here; at 90.7 miles (US 17): Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 138.7 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — Colonial National Historical Park, Cedar Creek & Belle Grove National Historical Park and Fort Monroe National Monument (6 total within detour distance). See the National Parks section for detour distances and tips on detours.
Possible but tiring. At 4.9 hours each way, an in-and-out day trip would put you behind the wheel for 9.9 hours — manageable with a long break at Chesapeake, VA, but most travelers stay overnight.
How this page is built
Compiled by the US Trip Planner planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, EIA for fuel prices, and NPS for national parks. See our methodology for refresh cadence and limitations.
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