Greenwich to Cheshire is 59.4 miles and takes about 1 hour 20 minutes via I 95 and Wilbur Cross Parkway, with a fuel budget near $10 and enough daylight to finish in a day. This short trip stays within Connecticut, moving from the Northeast's coastal region inland. The route is mostly highway, making it a straightforward and efficient drive. It's ideal for a quick transfer or a day trip, offering minimal fuss for travelers looking to cover ground without a significant time commitment.
Main Roads
Road
Distance
Duration
I 95
26.1 mi
35m
Wilbur Cross Parkway
14.1 mi
17m
Whitney Avenue
5.5 mi
7m
CT 8
5 mi
5m
Merritt Parkway
3 mi
4m
South Main Street
3 mi
3m
Field Point Road
0.2 mi
<1m
Arch Street
0.2 mi
<1m
Longest stretch:
I 95
— 26.1 mi, about 35m
Traffic on I-95
Hour-of-day weekday pattern from 40 FHWA count stations on your route.
Peak
5 PM
~4,341 veh/hr typical
Quietest
2 AM
~657 veh/hr
Peak-to-quiet ratio
6.6×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 5 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 Greenwich, CT and Cheshire, CT.
1
Start on West Elm Street
53 ft·5 sec·West Elm Street
2
Turn left onto Field Point Road
0.2 mi·26 sec·Field Point Road
Use the straight / right lanes.
3
Turn slight left onto Sound View Drive
0.2 mi·23 sec·Sound View Drive
4
Continue on Arch Street
0.2 mi·35 sec·Arch Street
5
Take the ramp
0.2 mi·29 sec
Toward I 95 North: New Haven
6
Merge onto I 95
26 mi·35 min·I 95
Use the straight / slight right lanes.
7
Take the exit
0.6 mi·1 min
Exit 27AToward CT 25, CT 8: Trumbull, WaterburyUse the right lane.
8
Continue on CT 8; CT 25
3.2 mi·3 min·CT 8; CT 25
Use the straight / right lanes.
9
Keep slight right at fork onto CT 8
1.8 mi·2 min·CT 8
Toward CT 8 North: Waterbury, New Haven
10
Take the exit
0.7 mi·1 min
Exit 6Toward CT 15 North: Merritt Parkway, New HavenUse the slight right lane.
11
Merge onto CT 15
3.0 mi·4 min·Merritt Parkway
Use the straight / slight right lanes.
12
Continue on CT 15
14 mi·17 min·Wilbur Cross Parkway
Use the straight / slight right lanes.
13
Take the exit
0.3 mi·47 sec
Exit 51Toward Whitney Avenue, HamdenUse the straight / right lanes.
14
Turn right onto Whitney Avenue
5.5 mi·7 min·Whitney Avenue
Use the left / straight / right lanes.
15
Continue on CT 10
3.0 mi·3 min·South Main Street
Use the straight lane.
16
Turn right onto CT 68; CT 70
0.1 mi·15 sec·Academy Road
17
Turn left onto Woodbury Court
305 ft·18 sec·Woodbury Court
18
Turn left
514 ft·37 sec
19
Arrive at destination
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
The midpoint is around 29.7 miles from Greenwich, CT, which is a good place for a longer meal and fuel stop.
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 12
5 decision points cluster between mile 0 and 50.4 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
6
0 mi into trip|~0m in|Field Point Road
Turn left onto Field Point Road
Lane positioning matters here
Use the straight / right lanes.
8
27 mi into trip|~37m in
Take the exit toward CT 25, CT 8: Trumbull, Waterbury
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the right lane.
Exit 27A
Toward CT 25, CT 8: Trumbull, Waterbury
6
30.8 mi into trip|~41m in|CT 8
Keep slight right at fork onto CT 8 toward CT 8 North: Waterbury, New Haven
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Toward CT 8 North: Waterbury, New Haven
8
32.6 mi into trip|~44m in
Take the exit toward CT 15 North: Merritt Parkway, New Haven
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 6
Toward CT 15 North: Merritt Parkway, New Haven
8
50.4 mi into trip|~1h 7m in
Take the exit toward Whitney Avenue, Hamden
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / right lanes.
Exit 51
Toward Whitney Avenue, Hamden
Fuel & Cost
Regular Gas
$10.37 one way
$20.73 round trip
$4.43/gal25.4 MPG avg21 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.93
$11.54
$23.08
premium
$5.30
$12.40
$24.79
diesel
$6.18
$14.45
$28.90
No toll roads detected on this route.
Drive Cost (one way)
Fuel
$10
Estimated CO2 emission: 20.8 kg one way.
Prices: EIA weekly data, 2026-10-12.
Driving Electric?
About $6 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
17.8
0
$6.24
$2.85
Efficient EV
14.9
0
$5.20
$2.38
EV Truck/SUV
23.8
0
$8.32
$3.80
Gas CO2
21 kg
EV CO2
7 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 Oct 17, 2026
Origin
Greenwich, CT
Afternoon
in Greenwich on Tuesday
Local time
1:48 PM
EDT
Current temp
53°F
Chance Rain Showers then Mostly Cloudy
N 13 mph29% chanceLive forecast
Freeze Warning
Freeze Warning issued October 17 at 2:20AM EDT until October 18 at 9:00AM EDT by NWS Upton NY
Destination
Cheshire, CT
Afternoon
in Cheshire on Tuesday
Local time
1:48 PM
EDT
Current temp
51°F
Slight Chance Rain Showers then Mostly Cloudy
N 13 mph22% chanceLive forecast
Freeze Warning
Freeze Warning issued October 17 at 2:20AM EDT until October 18 at 9:00AM EDT by NWS Upton NY
63°F
Monroe, CT
30 mi in
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
2 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
1h 20m on the road
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
More Details
What kind of drive is this?
You'll spend most of your time on highways, with 81% of the 59.4 miles on major roads like I 95. The longest contiguous stretch on the highway is 26.1 miles on I 95, before transitioning to the Wilbur Cross Parkway and then surface streets. Expect a high volume of exits and merging traffic, characteristic of a route that covers a significant portion on limited-access roads before reaching its destination.
81% highway — fuel and pacing are the main things to plan.
19 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 26.1 mi on I 95.
How Hard Is This Drive?
9/10
This is a straightforward highway drive that stays mostly on I 95 and Wilbur Cross Parkway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes early in the drive near Field Point Road.
Driving Effort9/10
Demanding - stay alert through the decision-heavy sections
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 59.4 miles you will encounter 12 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: near the start (Field Point Road): Lane positioning matters here; at 27 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 30.8 miles (CT 8): Highway fork - watch signs carefully. Multiple destination signs - pick the right one.
Elevation Profile
Mostly flat terrain
298 ft23 ft
Total Climb
595 ft
Total Descent
449 ft
Highest Point
298 ft
~42.4 mi in
Elevation Range
275 ft
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Greenwich, CT and Cheshire, CT, road signs point toward Waterbury, New Haven and Hamden.
Greenwich is a town of about 60,000 in Fairfield County, southwestern Connecticut. It is one of the wealthiest communities in America and is blessed with lush and beautiful scenery and many large and impressive houses.
Top landmarks
•Bruce Museum — museum in Greenwich, Connecticut
•Great Captain Island Light — lighthouse built 1868 in Connecticut, United States
•Cos Cob station — Railway station in Greenwich, Connecticut, United States
Doable as a same-day drive at 1h 20m. Total distance: 59.4 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 20m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (81%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 26.1 miles on I 95. The full list of main roads is in the Roads section above.
Yes — we found about 9 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 Cheshire, CT before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Yes. At under 2 hours behind the wheel, this works well for families — plan one quick stop if you have younger kids.
The main spots that need attention: near the start (Field Point Road): Lane positioning matters here; at 27 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 30.8 miles (CT 8): Highway fork - watch signs carefully. Multiple destination signs - pick the right one.
Yes — Weir Farm National Historical Park and Coltsville National Historical Park. See the National Parks section for detour distances and tips on detours.
Yes. A round trip is manageable in a single day if you plan a break at Cheshire, CT before heading back.
