Origin
Fairfield, CT
Night in Fairfield on Saturday
Local time
11:04 PM
EDT
Current temp
45°F
Unavailable
Live forecast
Trip from Fairfield, CT to Winsted, 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 21m
Distance
64 mi
103 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$10
one way
EV Charging
Unknown
Best Time to Leave
4 AM
1h 16m
★
6 AM
1h 22m
8 AM
1h 35m
10 AM
1h 26m
12 PM
1h 25m
3 PM
1h 27m
5 PM
1h 34m
8 PM
1h 18m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Fairfield, CT
David Kanigan
Winsted, CT
Wikimedia Commons
Trip Overview
If you are looking for a straightforward trip across Connecticut, this 64-mile drive from Fairfield to Winsted is a perfect candidate for a single-day journey. You can expect to spend about 1 hour and 21 minutes on the road, making it an efficient way to transition between the coast and the inland hills. With a fuel budget of approximately $10, it is an affordable excursion that fits easily into a morning or afternoon. Because the route relies on a mix of local roads and state highways rather than a singular interstate corridor, you should prepare for a steady pace rather than a high-speed sprint. It works best as a direct trip, allowing you to reach your destination without the need for an overnight stop.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| CT 8 | 58 mi | 1h 11m |
| I 95 | 4.3 mi | 5m |
| South Main Street | 0.3 mi | <1m |
| Park Place | 0.3 mi | <1m |
| Mill Plain Road | 0.2 mi | <1m |
| Post Road | <0.1 mi | <1m |
Longest stretch:
CT 8
— 58 mi, about 1h 11m
Turn-by-Turn Driving Directions
Step-by-step road directions between Fairfield, CT and Winsted, 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
26 mi
·
32 min
·
CT 8
Toward CT 8 North: Waterbury, New Haven
Use the straight / slight right lanes.
8
Continue on CT 8
0.4 mi
·
1 min
·
CT 8
Exit 31
Toward I 84 East: Hartford
Use the straight / slight right lanes.
9
Continue on CT 8
28 mi
·
34 min
·
CT 8
Exit 33
Toward I 84 West: Danbury
Use the straight / slight left lanes.
10
At end of road, turn right onto US 44; CT 8; CT 183
0.3 mi
·
52 sec
·
South Main Street
11
Turn right onto CT 8
0.2 mi
·
24 sec
·
Park Place
12
Continue on CT 8
0.1 mi
·
27 sec
·
Park Place
13
Arrive at destination
CT 8
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Mid-route town
Meal stop
32 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 14 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 32 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 95 decision points cluster between mile 0 and 8.6 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
0 mi into trip
|
~0m in
|
Mill Plain Road
Turn left onto Mill Plain Road
Navigation decision point
5
0.2 mi into trip
|
~0m in
Take the ramp toward I 95 North
Navigation decision point
Toward I 95 North
5
0.4 mi into trip
|
~1m in
|
I 95
Merge onto I 95
Merge point - match speed before joining. Lane positioning matters here
Use the straight / slight right lanes.
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
8.6 mi into trip
|
~11m in
|
CT 8
Keep slight right at fork onto CT 8 toward CT 8 North: Waterbury, New Haven
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward CT 8 North: Waterbury, New Haven
Fuel & Cost
Regular Gas
$10.30 one way
$20.61 round trip
$4.09/gal
25.4 MPG avg
22 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.50 | $11.34 | $22.67 |
| premium | $4.86 | $12.26 | $24.51 |
| diesel | $5.61 | $14.13 | $28.26 |
No toll roads detected on this route.
Drive Cost (one way)
Fuel
$10
Estimated CO2 emission: 22.4 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $7 in charging · 0 stops · 68% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 19.2 | 0 | $6.72 | $3.07 |
| Efficient EV | 16 | 0 | $5.60 | $2.56 |
| EV Truck/SUV | 25.6 | 0 | $8.96 | $4.10 |
Gas CO2
22 kg
EV CO2
7 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.
Destination
Winsted, CT
Night in Winsted on Saturday
Local time
11:04 PM
EDT
Current temp
39°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
6 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 21m 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?
Expect a turn-heavy local drive that demands your full attention as you transition away from the coastal infrastructure. You will navigate via Mill Plain Road, I-95 North, and CT-25, shifting gears as the character of the road evolves. Since this route maintains a zero-percent highway share in terms of dedicated limited-access travel for the duration, you will find yourself dealing with more intersections and varied speed limits than a typical interstate haul. The experience is defined by the constant movement through local landscapes rather than long, monotonous stretches of pavement. Stay alert for the frequent turns that define this winding path through the Connecticut countryside.
97% highway — fuel and pacing are the main things to plan.
13 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 58 mi on CT 8.
How Hard Is This Drive?
5/10
This is a straightforward highway drive that stays mostly on CT 8 and I 95. You will hit about 9 points where you need to pay attention to lane position or signs. The trickiest moment comes early in the drive near Mill Plain 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 64 miles you will encounter 9 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 (Mill Plain Road): Navigation decision point; at 0.2 miles: Navigation decision point; at 0.4 miles (I 95): Merge point - match speed before joining. Lane positioning matters here.
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 Winsted, CT, road signs point toward Waterbury and New Haven.
Waterbury
4.7 mi in
|
~6m
New Haven
8.6 mi in
|
~11m
|
via CT 8
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 1h 21m. Total distance: 64 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 21m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (97%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 58 miles on CT 8. The full list of main roads is in the Roads section above.
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 (Mill Plain Road): Navigation decision point; at 0.2 miles: Navigation decision point; at 0.4 miles (I 95): Merge point - match speed before joining. Lane positioning matters here.
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 Winsted, 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 Winsted, CT
More trips to Winsted, CT
Explore more options from Fairfield, CT or browse trips ending in Winsted, CT.
Looking for more statewide routes? Browse CT road trips.