Greenwich to Simsbury is 87.5 miles and takes about 2 hours 3 minutes via I 95 and Wilbur Cross Parkway, with a fuel budget near $14 and enough daylight to finish in a day. This drive stays within Connecticut, moving from the Northeast region towards another part of the Northeast. It's a relatively short trip that balances highway time with surface roads, making it a straightforward option for a day trip. You'll encounter mixed terrain, so expect some variety as you travel north.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
43.7 miles from Greenwich, CT
A natural place for your longest stop of the day
, about 59m into the drive
.
Main Roads
Road
Distance
Duration
I 95
26.1 mi
35m
Wilbur Cross Parkway
14.1 mi
17m
South Main Street
6.8 mi
8m
Waterville Road
5.6 mi
10m
Whitney Avenue
5.5 mi
7m
CT 8
5 mi
5m
Highland Avenue
4.4 mi
5m
Hopmeadow Street
4.2 mi
9m
Longest stretch:
I 95
— 26.1 mi, about 35m
Traffic on I-95
Hour-of-day weekday pattern from 24 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 Simsbury, 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
3.1 mi·3 min·South Main Street
Use the straight lane.
16
Continue on CT 10
4.4 mi·5 min·Highland Avenue
Use the straight / right lanes.
17
Continue on CT 10
0.2 mi·13 sec·Cheshire Road
18
Continue on CT 10
0.4 mi·29 sec·Norton Street
19
Continue on CT 10
3.6 mi·4 min·South Main Street
20
Continue on CT 10
2.4 mi·3 min·Queen Street
Use the straight / right lanes.
21
Continue on CT 10
1.7 mi·2 min·East Street
Use the straight / right lanes.
22
Continue on CT 10
1.4 mi·1 min·Farmington Avenue
Use the straight / right lanes.
23
Continue on CT 10
2.7 mi·3 min·Main Street
24
Continue on CT 10
5.6 mi·10 min·Waterville Road
Use the straight lane.
25
Turn left onto US 44; CT 10
0.7 mi·1 min·East Main Street
Use the left lane.
26
Turn right onto US 202; CT 10
0.8 mi·1 min·Simsbury Road
27
Continue on US 202; CT 10
4.2 mi·9 min·Hopmeadow Street
Use the straight lane.
28
Arrive at destination
US 202; CT 10
Trip Plan
Given the 2-hour drive time, leaving Greenwich in the morning allows ample time to reach Simsbury by midday. Since this is a single-day trip, you have flexibility in your departure time. The route is just under 90 miles, so you won't need extensive stops, but planning one brief break around the halfway point could be comfortable. Watch for the transition from I 95 to the Wilbur Cross Parkway, as traffic can shift there. With a fuel cost estimated at $14, budgeting a little extra is always wise.
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 43.7 miles from Greenwich, CT, or about 59m into the drive.
The longest continuous stretch on this route runs about 26.1 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 19 miles or 26m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 43.7 miles or 59m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 38m
Traffic, exits, and arrival timing usually matter more near Simsbury, CT than in the middle of the route.
Before You Leave
+
Open the route before leaving Greenwich, CT 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 Greenwich, CT
This is one driving day of about 87.5 miles and 2h 3m.
Your first comfortable stop window is around 19 miles from Greenwich, CT.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on I 95 for about 26.1 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 11
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
$15.47 one way
$30.94 round trip
$4.49/gal25.4 MPG avg31 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.92
$16.94
$33.88
premium
$5.29
$18.22
$36.44
diesel
$5.35
$18.43
$36.86
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$15
Meals
$25–$50
Total
$40–$65
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 30.6 kg one way.
Prices: EIA weekly data, 2026-06-01.
Driving Electric?
About $9 in charging
· 0 stops
· 68% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
26.3
0
$9.19
$4.20
Efficient EV
21.9
0
$7.66
$3.50
EV Truck/SUV
35
0
$12.25
$5.60
Gas CO2
31 kg
EV CO2
10 kg (68% 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 Jun 2, 2026
Origin
Greenwich, CT
Afternoon
in Greenwich on Wednesday
Local time
2:59 PM
EDT
Current temp
51°F
Mostly Clear
N 3 mph0% chanceLive forecast
Destination
Simsbury, CT
Afternoon
in Simsbury on Wednesday
Local time
2:59 PM
EDT
Current temp
47°F
Clear
W 2 mph0% 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
4 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
2h 3m 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.
National Parks Near This Route
Worth a detour if your schedule allows.
Weir Farm National Historical Park
National Historical Park
Visit the home and studio of America's most beloved Impressionist, J. Alden Weir, and walk in the footsteps of generations of world-class artists. Set amidst more than 60 acres of painterly woods, fie...
11 mi from route
~26 min detour
Free
near mile 15.1
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This drive features 55% highway, with the longest continuous stretch on I 95 covering 26.1 miles. You'll transition from highway driving to surface roads, with South Main Street being a key part of the latter half of your route. Expect typical suburban and town driving once you leave the interstate system. Keep an eye out for the change in traffic patterns as you move from faster-paced highway segments to more stop-and-go conditions on local streets.
55% highway, the rest on surface roads — varied driving throughout.
28 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?
8/10
This route mixes highway mileage with some local-road sections near the start or finish. 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 Effort8/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This is a demanding drive. With 11 significant decision points across 87.5 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: 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
277 ft24 ft
Total Climb
494 ft
Total Descent
409 ft
Highest Point
277 ft
~43.7 mi in
Elevation Range
254 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 Simsbury, 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
•Great Captain Island Light — lighthouse built 1868 in Connecticut, United States
•William E. Ward House — historic house located near Rye Brook, New York, United States
•Bruce Museum of Arts and Science — museum in Greenwich, Connecticut
Doable as a same-day drive at 2h 3m. Total distance: 87.5 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
2h 3m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (55%). Some complex stretches to watch for.
Scenic Drive
Mixed highway & surface route profile with national parks nearby.
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 11 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 Simsbury, CT 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. There are 11 rest areas along the route for bathroom stops.
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. 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 Simsbury, CT before heading back.
