How far is Cheshire, CT from Fairfield, CT?
The driving distance from Cheshire, CT to Fairfield, CT is about 37.3 miles (60 km), with a travel time of about 00h 51m by car.
- The straight-line flight distance is about 31.1 miles (50 km).
- For a round trip, plan for roughly 01h 42m 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 00h 51m.
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 New Haven County, 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 Cheshire and Fairfield.
Turn-by-Turn Driving Directions
Step-by-step road directions between Cheshire and Fairfield.
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1
Start on the route
157 m · 40 sec
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2
Turn right onto Woodbury Court
93 m · 15 sec · Woodbury Court
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3
Turn right onto Academy Road
610 ft · 18 sec · Academy Road
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4
At the end of the road, turn left onto South Main Street
3 mi · 4 min · South Main Street
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5
Continue on Whitney Avenue
5.4 mi · 7 min · Whitney Avenue
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6
Take the ramp slight right
1084 ft · 26 sec
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7
Merge slight left onto Wilbur Cross Parkway
13.8 mi · 18 min · Wilbur Cross Parkway
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8
Continue on Merritt Parkway
3 mi · 4 min · Merritt Parkway
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9
Take the exit slight right toward CT 8, CT 108: Bridgeport, Waterbury
1242 ft · 24 sec
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10
Keep slight left to continue on CT 8 South, CT 108 South: Bridgeport
2228 ft · 48 sec
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11
Keep slight left to continue on CT 8 South: Bridgeport
1.2 km · 2 min
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12
Merge slight left
4.5 mi · 5 min
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13
Keep slight right to continue on I 95 South: New York City
1719 ft · 42 sec
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14
Merge slight left
4.2 mi · 6 min
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15
Take the exit slight right toward Mill Plain Road
1525 ft · 42 sec
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16
Turn left onto Mill Plain Road
1655 ft · 39 sec · Mill Plain Road
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17
Turn right onto Post Road
57 m · 3 sec · Post Road
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18
Arrive at your destination
0 m · 1 sec · Post Road
Car Route Details
A richer read on the saved driving route between Cheshire and Fairfield.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Wilbur Cross Parkway
Merge slight left onto Wilbur Cross Parkway
13.8 mi · 00h 18m
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 Cheshire.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Cheshire to Fairfield?
The road trip is about 37.3 miles (60 km) and usually takes 00h 51m 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?
Orange is a useful midpoint, sitting about 18.4 miles from Cheshire and 19 miles from Fairfield.
How much longer is the road route than the straight-line distance?
The direct path is about 31.1 miles (50 km), while the road route adds roughly 6.2 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 4:48 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $5.21 one way or $10.41 round trip. Estimated CO2 is about 11.7 kg one way.
What should you check before leaving?
Before leaving, the latest forecast around Cheshire is Mostly Sunny.
Stop Ideas Near Orange
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 Orange.
Union Station
Bridgeport
Wallingford station
Meriden Transit Center
Flight Path Map
This map shows the direct air route between Cheshire and Fairfield. Straight-line distance: 31.08 mi (50.02 km).
#1 Cheshire
Town in Connecticut
| Population | 28,806 |
| Coordinates | 41.4989900, -72.9006600 |
| Altitude | 78 |
| 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: 60 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 14m |
| 40 mph (64.37 km/h) | 00h 55m |
| 50 mph (80.47 km/h) | 00h 44m |
| 60 mph (96.56 km/h) | 00h 37m |
| 70 mph (112.65 km/h) | 00h 31m |
| 80 mph (129 km/h) | 00h 27m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $5.21 | $10.41 |
| Mid-grade | $4.46 | $5.88 | $11.77 |
| Premium | $4.86 | $6.41 | $12.83 |
| Diesel | $6.00 | $7.92 | $15.83 |
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.