Origin
Chester, CT
Evening in Chester on Thursday
Local time
7:30 PM
EDT
Current temp
42°F
Unavailable
Live forecast
Trip from Chester, CT to New Haven, CT
Last recalculated Apr 16, 2026
Drive Time
49m
Distance
30.7 mi
49 km
Drive Score
6/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$5
one way
EV Charging
Unknown
Best Time to Leave
4 AM
0h 45m
★
6 AM
0h 49m
8 AM
0h 57m
10 AM
0h 52m
12 PM
0h 51m
3 PM
0h 52m
5 PM
0h 57m
8 PM
0h 47m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Chester, CT
Wikimedia Commons
New Haven, CT
Wikimedia Commons
Trip Overview
This 30.7-mile drive from Chester to New Haven, Connecticut, is a quick 49-minute journey that's perfect for a single day trip. With a modest fuel cost estimated at $5, it's an economical option for exploring the Northeast region. The route primarily uses local roads like Old Toll Road and Foxon Road, offering a more connected driving experience than a typical interstate cruise. Since there are no designated stops, you'll have the flexibility to pull over as needed. This short distance makes it easy to fit into any schedule, whether you're looking for a brief excursion or a component of a larger New England adventure.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 49m. Total distance: 30.7 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
49m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (3%). Some complex stretches to watch for.
Scenic Drive
Turn-heavy local drive route profile.
Drive Character
Expect a turn-heavy local drive for most of this 49-minute trip, with only a 3% highway share. The road unfolds primarily along Old Toll Road, Foxon Road, and Winthrop Road, meaning you'll be navigating through local communities rather than high-speed thoroughfares. The longest uninterrupted stretch you'll encounter is 7.3 miles on Old Toll Road, so plan for frequent adjustments in speed and direction. This profile suggests a driving experience that keeps you engaged with your surroundings, rather than a monotonous highway commute.
This route has more turning and local-road decision points than a simple highway run.
There are about 27 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Old Toll Road is the longest continuous segment at about 7.3 miles.
How Hard Is This Drive?
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. You will hit about 15 points where you need to pay attention to lane position or signs. The trickiest moment comes around 9.4 miles in near CT 80 / North Branford Road.
Driving Effort
5/10
Moderate - straightforward overall, but long enough or busy enough to require pacing
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 30.7 miles you will encounter 15 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
Where does it get tricky?
The main spots that need attention: at 9.4 miles (CT 80 / North Branford Road): Roundabout - know your exit number before entering; at 13.6 miles (CT 80 / Old Toll Road): Roundabout - know your exit number before entering; at 28.7 miles (US 5 / State Street): Lane positioning matters here.
Critical Maneuvers
5 of 15 key pointsThese are the spots where you need to pay the most attention. Preview them before you drive.
5
9.4 mi into trip
|
~15m in
|
CT 80 / North Branford Road
Enter roundabout onto CT 80 / North Branford Road
Roundabout - know your exit number before entering
5
13.6 mi into trip
|
~21m in
|
CT 80 / Old Toll Road
Enter roundabout onto CT 80 / Old Toll Road
Roundabout - know your exit number before entering
7
28.7 mi into trip
|
~45m in
|
US 5 / State Street
Turn left onto US 5 / State Street
Lane positioning matters here
Use the left lane.
7
29.5 mi into trip
|
~46m in
Take the exit toward Trumbull Street
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the straight / slight right lanes.
Exit 3
Toward Trumbull Street
6
30.4 mi into trip
|
~48m in
|
College Street
Turn sharp left onto College Street
Sharp turn - reduce speed on approach
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Old Toll Road | 7.3 mi | 10m |
| Foxon Road | 7.3 mi | 11m |
| Winthrop Road | 3.4 mi | 5m |
| North Branford Road | 2.8 mi | 4m |
| Deep River Road | 2.5 mi | 3m |
| Elm Street | 1.9 mi | 3m |
| Main Street | 1.3 mi | 2m |
| Middletown Avenue | 0.9 mi | 1m |
Longest stretch:
Old Toll Road
— 7.3 mi, about 10m
Turn-by-Turn Driving Directions
Step-by-step road directions between Chester, CT and New Haven, CT.
1
Start on CT 148
4 ft
·
3 sec
·
Water Street
2
Turn left onto Main Street
0.5 mi
·
1 min
·
Main Street
3
At end of road, turn right onto CT 154
0.4 mi
·
45 sec
·
Middlesex Turnpike
4
Continue on CT 154
0.8 mi
·
1 min
·
Main Street
5
Turn right onto CT 80
1.9 mi
·
3 min
·
Elm Street
6
Turn right onto CT 80
3.4 mi
·
5 min
·
Winthrop Road
7
Continue on CT 80
2.5 mi
·
3 min
·
Deep River Road
8
Enter roundabout onto CT 80
164 ft
·
3 sec
·
North Branford Road
9
Continue on CT 80
2.8 mi
·
4 min
·
North Branford Road
10
Continue on CT 80
1.3 mi
·
1 min
·
Old Toll Road
11
Enter roundabout onto CT 80
332 ft
·
5 sec
·
Old Toll Road
12
Continue on CT 80
5.9 mi
·
8 min
·
Old Toll Road
13
Continue on CT 80
7.3 mi
·
11 min
·
Foxon Road
Use the straight lane.
14
Continue on CT 80
0.8 mi
·
1 min
·
Foxon Boulevard
15
Continue on CT 80
490 ft
·
8 sec
·
Middletown Avenue
16
Continue on CT 17; CT 80
0.9 mi
·
1 min
·
Middletown Avenue
17
Turn right onto Ferry Street
403 ft
·
14 sec
·
Ferry Street
18
Turn left onto US 5
362 ft
·
8 sec
·
State Street
Use the left lane.
19
Turn right onto Warren Place
60 ft
·
2 sec
·
Warren Place
20
Take the ramp
0.2 mi
·
27 sec
Toward I 91 South
21
Merge onto I 91
0.6 mi
·
53 sec
·
I 91
22
Take the exit
0.4 mi
·
48 sec
Exit 3
Toward Trumbull Street
Use the straight / slight right lanes.
23
Turn straight onto Trumbull Street
0.2 mi
·
25 sec
·
Trumbull Street
Use the straight lane.
24
Turn left onto Temple Street
0.2 mi
·
19 sec
·
Temple Street
25
Turn right onto Grove Street
0.1 mi
·
18 sec
·
Grove Street
26
Turn sharp left onto College Street
0.3 mi
·
27 sec
·
College Street
27
Arrive at destination
College Street
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 15.3 mi from Chester, CT · 24m into the drive
Mid-route town
Meal stop
15 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 30.7 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 15.3 miles from Chester, CT, which is a good place for a longer meal and fuel stop.
Arriving in New Haven, CT
Allow a few extra minutes for the final approach into New Haven, CT if you are unfamiliar with the area.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Fuel & Cost
Regular Gas
$4.94 one way
$9.88 round trip
$4.09/gal
25.4 MPG avg
11 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.50 | $5.44 | $10.88 |
| premium | $4.86 | $5.88 | $11.76 |
| diesel | $5.61 | $6.78 | $13.56 |
Estimated Tolls: $0.51
Old Toll Road
(7.3 mi)
$0.51
Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.
Drive Cost (one way)
Fuel
$5
Tolls
$1
Total
$5
Estimated CO2 emission: 10.7 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $3 in charging · 0 stops · 64% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 9.2 | 0 | $3.22 | $1.47 |
| Efficient EV | 7.7 | 0 | $2.69 | $1.23 |
| EV Truck/SUV | 12.3 | 0 | $4.30 | $1.96 |
Gas CO2
11 kg
EV CO2
4 kg (64% 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.
Destination
New Haven, CT
Evening in New Haven on Thursday
Local time
7:30 PM
EDT
Current temp
43°F
Unavailable
Live forecast
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 warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
49m on the road
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
Frequently Asked Questions
The drive from Chester, CT to New Haven, CT covers 30.7 miles and takes about 49m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Old Toll Road, Foxon Road, Winthrop Road. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 15.3 miles from Chester, CT. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $4.94 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.
This drive requires moderate attention. Across 30.7 miles you will encounter 15 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
The main spots that need attention: at 9.4 miles (CT 80 / North Branford Road): Roundabout - know your exit number before entering; at 13.6 miles (CT 80 / Old Toll Road): Roundabout - know your exit number before entering; at 28.7 miles (US 5 / State Street): Lane positioning matters here.
The route from Chester, CT to New Haven, CT does not surface many named destination signs beyond the main corridor.
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