Spanning 207.1 miles across Virginia, this trip connects Winchester to Hampton in approximately 3 hours and 32 minutes. Because the route relies on local roads like East Boscawen Street, South Kent Street, and Millwood Avenue rather than major interstates, it functions best as a focused one-day journey. You should budget roughly $33 for fuel to cover the distance comfortably. Since both cities reside within the Southeast region, you won't experience a major climate or cultural shift, but the shift from the interior to the coast is notable. If you prefer a relaxed pace, plan for at least one stop to break up the drive. This is a straightforward excursion for those who prefer navigating local corridors over high-speed highway travel.
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
103.4 miles from Winchester, VA
A natural place for your longest stop of the day
, about 2h 23m into the drive
.
Main Roads
Road
Distance
Duration
US 17
80 mi
1h 38m
I 64
64.2 mi
1h 11m
Korean War Veterans Memorial Highway
13 mi
14m
James Madison Highway
11.6 mi
16m
Winchester Road
10.2 mi
16m
John Singleton Mosby Highway
8.8 mi
12m
Millwood Pike
5.7 mi
8m
Eastern Bypass
4.9 mi
6m
Longest stretch:
US 17
— 80 mi, about 1h 38m
Turn-by-Turn Driving Directions
Step-by-step road directions between Winchester, VA and Hampton, VA.
1
Start on US 11; US 522
0.1 mi·32 sec·North Cameron Street
2
Turn left onto East Boscawen Street
427 ft·17 sec·East Boscawen Street
3
Turn right onto South Kent Street
0.6 mi·1 min·South Kent Street
4
Turn left onto US 17; US 50; US 522
0.7 mi·1 min·Millwood Avenue
5
Turn left onto US 17; US 50; US 522
0.2 mi·39 sec·Millwood Avenue
Use the left lane.
6
Continue on US 17; US 50; US 522
5.7 mi·8 min·Millwood Pike
7
Continue on US 17; US 50
2.1 mi·3 min·John Mosby Highway
8
Continue on US 17; US 50
8.8 mi·12 min·John Singleton Mosby Highway
9
Turn right onto US 17
7.8 mi·13 min·Winchester Road
10
Keep slight left at fork onto US 17; VA 55
5.0 mi·5 min·US 17; VA 55
Toward I 66 East, US 17 South, VA 55 East: Marshall, FredericksburgUse the straight lane.
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: FredericksburgUse 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: RichmondUse the straight / slight right lanes.
19
Take the exit
1.9 mi·2 min
Exit 84AToward I 295 South: Williamsburg, Norfolk, Va BeachUse 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 28AToward I 64 East: Norfolk, Virginia BeachUse the straight / slight right lanes.
22
Merge onto I 64
64 mi·1 hr 11 min·I 64
Use the straight / slight right lanes.
23
Take the exit
0.1 mi·25 sec
Exit 265CToward Armistead Avenue, Langley Air Force BaseUse the straight / slight right lanes.
24
Keep slight right at fork
199 ft·6 sec
Toward Armistead Avenue, Langley Air Force BaseUse the left / right lanes.
25
Turn straight onto Rip Rap Road
0.2 mi·21 sec·Rip Rap Road
26
Turn sharp left onto VA 134
0.4 mi·1 min·North Armistead Avenue
27
Turn left onto VA 351
0.3 mi·39 sec·West Pembroke Avenue
28
Turn right onto North King Street
524 ft·19 sec·North King Street
29
Continue on North King Street
432 ft·18 sec·North King Street
30
Arrive at destination
North King Street
Trip Plan
For the smoothest experience, plan your departure early to account for the frequent turns required by the local road layout. Since you have 3 hours and 32 minutes of driving time ahead, prioritize at least one planned stop to stretch your legs and refresh your focus. Keep your $33 fuel budget in mind, and consider fueling up before you leave Winchester to avoid searching for stations during the more technical portions of the drive. The primary advantage of this trip is its flexibility, so don't feel pressured to rush; use the local nature of the route to your benefit. Pay close attention to your GPS navigation, as the reliance on streets like Millwood Avenue means you will need to be alert for upcoming turns throughout the journey.
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 103.4 miles from Winchester, VA, or about 2h 23m into the drive.
The longest continuous stretch on this route runs about 80 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 45 miles or 1h 7m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 103.4 miles or 2h 23m 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 37m
Traffic, exits, and arrival timing usually matter more near Hampton, VA than in the middle of the route.
Before You Leave
+
Open the route before leaving Winchester, 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 Winchester, VA
This is one driving day of about 206.7 miles and 4h 21m.
Your first comfortable stop window is around 45 miles from Winchester, 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 80 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 20
5 decision points cluster between mile 26.3 and 205.7 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
8
26.3 mi into trip|~42m in|US 17; VA 55
Keep slight left at fork onto US 17; VA 55 toward I 66 East, US 17 South, VA 55 East: Marshall, Fredericksburg
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight lane.
Toward I 66 East, US 17 South, VA 55 East: Mars...
8
125.2 mi into trip|~2h 47m 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
140 mi into trip|~3h 3m 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
8
205.5 mi into trip|~4h 18m in
Take the exit toward Armistead Avenue, Langley Air Force Base
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 265C
Toward Armistead Avenue, Langley Air Force Base
9
205.7 mi into trip|~4h 18m in
Keep slight right at fork toward Armistead Avenue, Langley Air Force Base
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the left / right lanes.
Toward Armistead Avenue, Langley Air Force Base
Fuel & Cost
Regular Gas
$32.32 one way
$64.65 round trip
$3.97/gal25.4 MPG avg72 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.34
$35.34
$70.68
premium
$4.70
$38.26
$76.51
diesel
$5.61
$45.64
$91.27
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$32
Meals
$25–$50
Total
$57–$82
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 72.3 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $22 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
62
0
$21.70
$9.92
Efficient EV
51.7
0
$18.09
$8.27
EV Truck/SUV
82.7
1
$28.94
$13.23
Gas CO2
72 kg
EV CO2
24 kg (67% 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 Apr 13, 2026
Origin
Winchester, VA
Late night
in Winchester on Sunday
Local time
12:33 AM
EDT
Current temp
83°F
Unavailable
Live forecast
Destination
Hampton, VA
Late night
in Hampton on Sunday
Local time
12:33 AM
EDT
Current temp
82°F
Mostly Sunny
SW 18 mph2% 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
1 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 21m 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
~2 min detour
$15
near mile 185.3
Park Closure: Rehabilitation of Colonial Parkway Continues
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...
3 mi from route
~6 min detour
Free
near mile 206.7
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...
12 mi from route
~30 min detour
Free
near mile 7.1
At the confluence of the Shenandoah and Potomac rivers, on the ancestral home of the Tuscarora and Shawnee people, lies Harpers Ferry. Here you can explore John Brown's Raid against slavery. Find your...
24 mi from route
~59 min detour
$20
near mile 14.3
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
~65 min detour
Free
near mile 142.6
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!
26 mi from route
~65 min detour
Free
near mile 21.4
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a turn-heavy local drive that demands your full attention behind the wheel. With a 0% highway share, this route avoids the monotony of interstate cruising in favor of a more hands-on experience along local thoroughfares. You will navigate through varied town layouts and neighborhood streets, making the drive feel intimate and rhythmic rather than fast-paced. Because the journey relies entirely on local navigation, the road character remains consistent in its requirement for frequent adjustments. It is a technical, steady drive that rewards drivers who enjoy staying engaged with the road throughout the entire 207.1-mile stretch.
70% highway — fuel and pacing are the main things to plan.
30 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 80 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 26.3 miles in near US 17; VA 55.
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 20 significant decision points across 206.7 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 26.3 miles (US 17; VA 55): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 125.2 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 140 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Elevation Profile
Mostly flat terrain
708 ft7 ft
Total Climb
222 ft
Total Descent
923 ft
Highest Point
708 ft
Elevation Range
701 ft
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Winchester, VA and Hampton, VA, road signs point toward Fredericksburg, Norfolk, Va Beach and Virginia Beach.
Fredericksburg
26.3 mi in|~42m|via US 17; VA 55
Norfolk
125.2 mi in|~2h 47m
Va Beach
125.2 mi in|~2h 47m
Virginia Beach
140 mi in|~3h 3m
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 4h 21m. Total distance: 206.7 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
4h 21m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (70%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 80 miles on US 17. The full list of main roads is in the Roads section above.
Yes — we found about 1 rest area or service plaza 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 Hampton, 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 1 rest area along the route for bathroom stops.
The main spots that need attention: at 26.3 miles (US 17; VA 55): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 125.2 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 140 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, Fort Monroe National Monument and Cedar Creek & Belle Grove National Historical Park (6 total within detour distance). See the National Parks section for detour distances and tips on detours.
Possible but tiring. At 4.4 hours each way, an in-and-out day trip would put you behind the wheel for 8.7 hours — manageable with a long break at Hampton, VA, but most travelers stay overnight.
