How far is Winsted, CT from Fairfield, CT?
The driving distance from Winsted, CT to Fairfield, CT is about 63.7 miles (102.5 km), with a travel time of about 01h 03m by car.
- The straight-line flight distance is about 54.9 miles (88.4 km).
- For a round trip, plan for roughly 02h 07m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 01h 03m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
You are leaving earlier than the recommended window, which gives you extra margin for breaks and traffic.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Town in Connecticut, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Winsted and Fairfield.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winsted and Fairfield.
-
1
Start on Park Place
31 m · 12 sec · Park Place
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2
Turn left onto South Main Street
2366 ft · 1 min · South Main Street
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3
Continue on CT 8 SOUTH: Torrington, Waterbury
58 mi · 1 hr 10 min
-
4
Keep slight right to continue on I 95 South: New York City
1719 ft · 42 sec
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5
Merge slight left
4.2 mi · 6 min
-
6
Take the exit slight right toward Mill Plain Road
1525 ft · 40 sec
-
7
Turn left onto Mill Plain Road
1655 ft · 39 sec · Mill Plain Road
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8
Turn right onto Post Road
57 m · 3 sec · Post Road
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9
Arrive at your destination
0 m · 1 sec · Post Road
Car Route Details
A richer read on the saved driving route between Winsted and Fairfield.
Straightforward drive
The saved road route has a manageable number of maneuvers and should be easy to follow with normal attention to signs.
CT 8 SOUTH
Continue on CT 8 SOUTH: Torrington, Waterbury
58 mi · 01h 10m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Mostly Sunny near Winsted.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winsted to Fairfield?
The road trip is about 63.7 miles (102.5 km) and usually takes 01h 03m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Naugatuck is a useful midpoint, sitting about 31.8 miles from Winsted and 31.9 miles from Fairfield.
How much longer is the road route than the straight-line distance?
The direct path is about 54.9 miles (88.4 km), while the road route adds roughly 8.8 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 4:22 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $8.88 one way or $17.75 round trip. Estimated CO2 is about 20 kg one way.
What should you check before leaving?
Before leaving, the latest forecast around Winsted is Mostly Sunny.
Stop Ideas Near Naugatuck
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Naugatuck.
Wallingford station
Meriden Transit Center
Union Station
Berlin
Flight Path Map
This map shows the direct air route between Winsted and Fairfield. Straight-line distance: 54.91 mi (88.37 km).
#1 Winsted
City in Connecticut, United States
| Population | 7,712 |
| Coordinates | 41.9212100, -73.0601100 |
| Altitude | 216 |
| Country | United States |
#2 Fairfield
Town in Connecticut, United States of America
| Population | 62,215 |
| Coordinates | 41.1412100, -73.2637300 |
| Altitude | 10 |
| Country | United States |
End: Post Road (-73.263724, 41.141186)
Estimated Travel Time
Distance: 102 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 07m |
| 40 mph (64.37 km/h) | 01h 35m |
| 50 mph (80.47 km/h) | 01h 16m |
| 60 mph (96.56 km/h) | 01h 03m |
| 70 mph (112.65 km/h) | 00h 54m |
| 80 mph (129 km/h) | 00h 47m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $8.88 | $17.75 |
| Mid-grade | $4.46 | $10.03 | $20.06 |
| Premium | $4.86 | $10.93 | $21.86 |
| Diesel | $6.00 | $13.49 | $26.99 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in Connecticut · Apr 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.