Origin
Chesapeake, VA
Morning in Chesapeake on Friday
Local time
6:27 AM
EDT
Current temp
52°F
Unavailable
Live forecast
Trip from Chesapeake, VA to Glasgow, VA
Compiled and reviewed by the Trip.ovh planning team at COD Solutions Oy · Last reviewed Apr 17, 2026 · Editorial standards
Drive Time
4h 43m
Distance
245.4 mi
395 km
Drive Score
8/10
Great drive
Same Day?
Yes, doable
Fuel Cost
$38
one way
EV Charging
Unknown
Best Time to Leave
4 AM
4h 30m
★
6 AM
4h 44m
8 AM
5h 11m
10 AM
4h 53m
12 PM
4h 51m
3 PM
4h 55m
5 PM
5h 9m
8 PM
4h 36m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Chesapeake, VA
Wikimedia Commons
Glasgow, VA
Sinitta Leunen
Trip Overview
The drive from Chesapeake, VA to Glasgow, VA covers 245.4 miles and takes about 4h 43m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Poindexter Street, I 464 North, I 264 East for much of the mileage, and the overall profile is turn-heavy local drive. At current regular gas prices, budget about $38.38 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
122.7 miles from Chesapeake, VA
A natural place for your longest stop of the day , about 2h 21m into the drive .
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 4h 43m. Total distance: 245.4 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
4h 43m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (0%). Straightforward navigation.
Scenic Drive
Turn-heavy local drive route profile.
Drive Character
Expect a 4h 43m drive with frequent turns across 245.4 miles of local and secondary roads.
This route has more turning and local-road decision points than a simple highway run.
There are about 34 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Poindexter Street is one of the defining roads on this drive.
How Hard Is This Drive?
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. There are only a few real navigation decisions along the way.
Driving Effort
3/10
Easy - simple navigation with a manageable amount of wheel time
Balances navigation complexity with total wheel time.
This is a straightforward 4h 43m drive. You will face about 0 decision points, but nothing that requires special attention if you follow navigation.
Where does it get tricky?
This route does not have any notably tricky sections. Most of the drive from Chesapeake, VA to Glasgow, VA is straightforward, with well-signed roads and simple exits.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Poindexter Street | — | — |
| I 464 North | — | — |
| I 264 East | — | — |
| Waterside Drive | — | — |
| Saint Paul's Boulevard | — | — |
| Saint Pauls Boulevard | — | — |
| Monticello Avenue | — | — |
| Church Street | — | — |
Some road-level metrics are being recalculated.
Longest stretch:
Poindexter Street
— detailed segment metrics are refreshing.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake, VA and Glasgow, VA.
1
Start on D Street
413 ft
·
21 sec
·
D Street
2
At the end of the road, turn right onto Poindexter Street
0.3 mi
·
29 sec
·
Poindexter Street
3
Take the ramp straight toward I 464 North
0.2 mi
·
18 sec
·
I 464 North
4
Merge slight left
1.2 mi
·
1 min
5
Keep slight left to continue on I 264 East: Waterside Drive, Saint Paul Boulevard, Downtown, Norfolk
0.7 mi
·
1 min
·
I 264 East: Waterside Drive, Saint Paul Boulevard, Downtown, Norfolk
6
Keep slight left to continue on Waterside Drive, St Paul's Boulevard
0.2 mi
·
27 sec
·
Waterside Drive, St Paul's Boulevard
7
Keep slight left to continue on Saint Paul's Boulevard
0.3 mi
·
53 sec
·
Saint Paul's Boulevard
8
Turn right onto Saint Pauls Boulevard
0.6 mi
·
1 min
·
Saint Pauls Boulevard
9
Continue on Monticello Avenue
1.2 mi
·
2 min
·
Monticello Avenue
10
Turn left onto Church Street
486 ft
·
14 sec
·
Church Street
11
Continue on Granby Street
4.0 mi
·
9 min
·
Granby Street
12
Turn left onto I 64
0.2 mi
·
26 sec
·
I 64
13
Merge slight left onto Hampton Roads Beltway
3.8 mi
·
5 min
·
Hampton Roads Beltway
14
Continue on Hampton Roads Bridge-Tunnel
3.5 mi
·
4 min
·
Hampton Roads Bridge-Tunnel
15
Continue on Hampton Roads Beltway
5.9 mi
·
7 min
·
Hampton Roads Beltway
16
Keep slight left
61 mi
·
1 hr 7 min
17
Take the exit slight right toward I 295, US 60: Washington, Rocky Mount NC
0.5 mi
·
32 sec
·
I 295, US 60: Washington, Rocky Mount NC
18
Keep slight right to continue on I 295 North: Washington
1.3 mi
·
2 min
·
I 295 North: Washington
19
Merge slight left onto Korean War Veterans Memorial Highway
23 mi
·
24 min
·
Korean War Veterans Memorial Highway
20
Keep slight right to continue on I 64 West: Charlottesville
0.6 mi
·
55 sec
·
I 64 West: Charlottesville
21
Merge slight left onto I 64 West: Charlottesville
120 mi
·
2 hr 10 min
·
I 64 West: Charlottesville
22
Keep slight left
2.9 mi
·
3 min
23
Take the exit slight right toward US 60 East: Buena Vista
0.3 mi
·
40 sec
·
US 60 East: Buena Vista
24
Continue on East Midland Trail
3.0 mi
·
3 min
·
East Midland Trail
25
Continue on 29th Street
0.6 mi
·
40 sec
·
29th Street
26
Take the exit right
302 ft
·
8 sec
27
Merge slight left onto Beech Avenue
0.4 mi
·
31 sec
·
Beech Avenue
28
Continue on Sycamore Avenue
2.7 mi
·
3 min
·
Sycamore Avenue
29
Continue on Glasgow Highway
6.1 mi
·
7 min
·
Glasgow Highway
30
Turn right onto Rockbridge Road
0.5 mi
·
56 sec
·
Rockbridge Road
31
Turn right onto Blue Ridge Road
0.3 mi
·
38 sec
·
Blue Ridge Road
32
Turn right onto McCulloch Street
148 ft
·
9 sec
·
McCulloch Street
33
Turn right
92 ft
·
7 sec
34
Arrive at your destination
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 122.7 miles from Chesapeake, VA, or about 2h 21m into the drive.
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 54 miles or 1h 2m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 122.7 miles or 2h 21m 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 52m
Traffic, exits, and arrival timing usually matter more near Glasgow, 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 245.4 miles and 4h 43m.
Your first comfortable stop window is around 54 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.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 122.7 mi from Chesapeake, VA · 2h 21m into the drive
Mid-route town
Meal stop
123 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 54 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 122.7 miles from Chesapeake, VA, which is a good place for a longer meal and fuel stop.
Arriving in Glasgow, VA
The final approach into Glasgow, 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 Glasgow, VA.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Fuel & Cost
Regular Gas
$38.38 one way
$76.75 round trip
$3.97/gal
25.4 MPG avg
86 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.34 | $41.96 | $83.92 |
| premium | $4.70 | $45.42 | $90.84 |
| diesel | $5.61 | $54.18 | $108.36 |
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$38
Meals
$25–$50
Total
$63–$88
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 85.9 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $26 in charging · 0 stops · 66% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 73.6 | 0 | $25.77 | $11.78 |
| Efficient EV | 61.4 | 0 | $21.47 | $9.82 |
| EV Truck/SUV | 98.2 | 1 | $34.36 | $15.71 |
Gas CO2
86 kg
EV CO2
29 kg (66% 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
Glasgow, VA
Morning in Glasgow on Friday
Local time
6:27 AM
EDT
Current temp
47°F
Unavailable
Live forecast
53°F
Ashland, VA
123 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
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
4h 43m 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 Chesapeake, VA to Glasgow, VA covers 245.4 miles and takes about 4h 43m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Poindexter Street, I 464 North, I 264 East. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 122.7 miles from Chesapeake, VA. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $38.38 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 straightforward 4h 43m drive. You will face about 0 decision points, but nothing that requires special attention if you follow navigation.
This route does not have any notably tricky sections. Most of the drive from Chesapeake, VA to Glasgow, VA is straightforward, with well-signed roads and simple exits.
The route from Chesapeake, VA to Glasgow, VA does not surface many named destination signs beyond the main corridor.
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. Pages are published only after passing our data-quality checks; our methodology page documents refresh cadence, editorial standards, and known limitations.
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