Origin
Fairfield, CT
Late night in Fairfield on Sunday
Local time
12:34 AM
EDT
Current temp
45°F
Unavailable
Live forecast
Trip from Fairfield, CT to Windsor, CT
Compiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Apr 19, 2026 · Editorial standards
Drive Time
1h 27m
Distance
67.1 mi
108 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$11
one way
EV Charging
Unknown
Best Time to Leave
4 AM
1h 21m
★
6 AM
1h 27m
8 AM
1h 41m
10 AM
1h 32m
12 PM
1h 31m
3 PM
1h 33m
5 PM
1h 40m
8 PM
1h 23m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Fairfield, CT
David Kanigan
Windsor, CT
Wikimedia Commons
Trip Overview
This 67.1-mile drive from Fairfield, CT, to Windsor, CT, will take approximately 1 hour and 27 minutes. Designed as a single-day trip, this route is best tackled when you have a full day to explore. With a projected fuel cost of around $11, it's an economical option for a quick journey within the Northeast region. The drive primarily utilizes local roads, indicated by its 'turn-heavy local drive' profile, suggesting a need for attentive navigation rather than a straightforward highway cruise. Expect a more engaging driving experience with frequent turns and changes in scenery as you make your way north.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Wilbur Cross Parkway | 27 mi | 33m |
| I 91 | 24.4 mi | 30m |
| CT 8 | 5 mi | 5m |
| I 95 | 4.3 mi | 5m |
| Merritt Parkway | 3 mi | 4m |
| Bloomfield Avenue | 1 mi | 2m |
| Mill Plain Road | 0.2 mi | <1m |
| Poquonock Avenue | <0.1 mi | <1m |
Longest stretch:
Wilbur Cross Parkway
— 27 mi, about 33m
Turn-by-Turn Driving Directions
Step-by-step road directions between Fairfield, CT and Windsor, CT.
1
Start on US 1
186 ft
·
12 sec
·
Post Road
2
Turn left onto Mill Plain Road
0.2 mi
·
22 sec
·
Mill Plain Road
3
Take the ramp
0.2 mi
·
27 sec
Toward I 95 North
4
Merge onto I 95
4.3 mi
·
5 min
·
I 95
Use the straight / slight right lanes.
5
Take the exit
0.6 mi
·
1 min
Exit 27A
Toward CT 25, CT 8: Trumbull, Waterbury
Use the right lane.
6
Continue on CT 8; CT 25
3.2 mi
·
3 min
·
CT 8; CT 25
Use the straight / right lanes.
7
Keep slight right at fork onto CT 8
1.8 mi
·
2 min
·
CT 8
Toward CT 8 North: Waterbury, New Haven
8
Take the exit
0.7 mi
·
1 min
Exit 6
Toward CT 15 North: Merritt Parkway, New Haven
Use the slight right lane.
9
Merge onto CT 15
3.0 mi
·
4 min
·
Merritt Parkway
Use the straight / slight right lanes.
10
Continue on CT 15
27 mi
·
33 min
·
Wilbur Cross Parkway
Use the straight / slight right lanes.
11
Take the exit
0.3 mi
·
38 sec
Exit 65A
Toward I 91 North, CT 66 East: Hartford, Middletown
Use the slight right lane.
12
Merge onto I 91
18 mi
·
21 min
·
I 91
Use the straight / slight right lanes.
13
Keep slight right at fork onto I 91
6.7 mi
·
8 min
·
I 91
Use the straight / slight right lanes.
14
Take the exit
0.2 mi
·
32 sec
Exit 37
Toward CT 305: Bloomfield Avenue, Windsor Center
Use the straight / slight right lanes.
15
Turn right onto CT 305
1.0 mi
·
2 min
·
Bloomfield Avenue
Use the right lane.
16
At end of road, turn right onto CT 75
394 ft
·
15 sec
·
Poquonock Avenue
Use the left / right lanes.
17
Continue on Broad Street
56 ft
·
2 sec
·
Broad Street
Use the straight / left lanes.
18
Arrive at destination
Broad Street
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Mid-route town
Meal stop
34 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 15 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 33.6 miles from Fairfield, 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 145 decision points cluster between mile 4.7 and 67 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
8
4.7 mi into trip
|
~6m 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
8
10.3 mi into trip
|
~13m 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
41.1 mi into trip
|
~53m in
Take the exit toward I 91 North, CT 66 East: Hartford, Middletown
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 65A
Toward I 91 North, CT 66 East: Hartford, Middle...
8
65.9 mi into trip
|
~1h 24m in
Take the exit toward CT 305: Bloomfield Avenue, Windsor Center
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 37
Toward CT 305: Bloomfield Avenue, Windsor Cente...
7
67 mi into trip
|
~1h 27m in
|
CT 75 / Poquonock Avenue
At end of road, turn right onto CT 75 / Poquonock Avenue
Lane positioning matters here
Use the left / right lanes.
Fuel & Cost
Regular Gas
$10.80 one way
$21.60 round trip
$4.09/gal
25.4 MPG avg
24 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.50 | $11.89 | $23.77 |
| premium | $4.86 | $12.85 | $25.70 |
| diesel | $5.61 | $14.81 | $29.63 |
No toll roads detected on this route.
Drive Cost (one way)
Fuel
$11
Estimated CO2 emission: 23.5 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $7 in charging · 0 stops · 65% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 20.1 | 0 | $7.05 | $3.22 |
| Efficient EV | 16.8 | 0 | $5.87 | $2.68 |
| EV Truck/SUV | 26.8 | 0 | $9.39 | $4.29 |
Gas CO2
23 kg
EV CO2
8 kg (65% 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
Windsor, CT
Late night in Windsor on Sunday
Local time
12:34 AM
EDT
Current temp
42°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
3 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 27m 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.
What kind of drive is this?
This route is characterized by its 'turn-heavy local drive' profile, meaning you won't be spending any time on highways, as indicated by the 0% highway share. The drive is composed of local roads like Mill Plain Road and CT 25, requiring constant engagement with steering and navigation. With no long, uninterrupted stretches, you'll experience a dynamic driving experience with frequent changes in direction. This style of driving emphasizes your connection to the local landscape as you navigate through various communities.
95% highway — fuel and pacing are the main things to plan.
18 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 27 mi on Wilbur Cross Parkway.
How Hard Is This Drive?
9/10
This is a straightforward highway drive that stays mostly on Wilbur Cross Parkway and I 91. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 4.7 miles in.
Driving Effort
9/10
Demanding - stay alert through the decision-heavy sections
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 67.1 miles you will encounter 14 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 4.7 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 10.3 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 41.1 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Fairfield, CT and Windsor, CT, road signs point toward Waterbury, New Haven and Middletown.
Waterbury
4.7 mi in
|
~6m
New Haven
8.6 mi in
|
~11m
|
via CT 8
Middletown
41.1 mi in
|
~53m
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 1h 27m. Total distance: 67.1 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 27m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (95%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 27 miles on Wilbur Cross Parkway. The full list of main roads is in the Roads section above.
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 Windsor, 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: at 4.7 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 10.3 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 41.1 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. 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 Windsor, CT before heading back.
How this page is built
Compiled by the US Trip Planner planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, EIA for fuel prices, and NPS for national parks. See our methodology for refresh cadence and limitations.
Was this helpful?
Thanks for your feedback!
Your tip has been submitted. Thanks!
/500
Recent Tips
·
Explore More
Continue From Windsor, CT
Explore more options from Fairfield, CT or browse trips ending in Windsor, CT.
Looking for more statewide routes? Browse CT road trips.