How far is Fairfield, CT from Windham, CT?
The driving distance from Fairfield, CT to Windham, CT is about 88.5 miles (142.4 km), with a travel time of about 01h 55m by car.
- The straight-line flight distance is about 69.1 miles (111.2 km).
- For a round trip, plan for roughly 03h 50m 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 55m.
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, USA
Route Weather Snapshot
Check the forecast at both ends before you head out.
Driving Route Map
The map below follows the saved road route between Fairfield and Windham.
Turn-by-Turn Driving Directions
Step-by-step road directions between Fairfield and Windham.
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1
Start on Post Road
57 m · 12 sec · Post Road
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2
Turn left onto Mill Plain Road
1048 ft · 22 sec · Mill Plain Road
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3
Take the ramp right toward I 95 North
1126 ft · 27 sec
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4
Merge slight left
4.3 mi · 6 min
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5
Take the exit slight right toward CT 25, CT 8: Trumbull, Waterbury
1 km · 1 min
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6
Continue straight
3.2 mi · 3 min
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7
Keep slight right to continue on CT 8 North: Waterbury, New Haven
1.8 mi · 2 min
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8
Take the exit slight right toward CT 15 North: Merritt Parkway, New Haven
1.2 km · 2 min
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9
Merge slight left onto Merritt Parkway
3 mi · 4 min · Merritt Parkway
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10
Continue on Wilbur Cross Parkway
27 mi · 34 min · Wilbur Cross Parkway
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11
Take the exit slight right toward I 91 North, CT 66 East: Hartford, Middletown
1815 ft · 39 sec
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12
Merge slight left
13.6 mi · 16 min
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13
Take the exit slight right toward CT 3 North: Glastonbury, Old Wethersfield
952 ft · 23 sec
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14
Keep slight left to continue on CT 3 North: Glastonbury
1515 ft · 37 sec
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15
Merge slight left
1.9 mi · 3 min
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16
Keep slight right to continue on CT 2 East: Norwich
1622 ft · 34 sec
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17
Merge slight left
2125 ft · 33 sec
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18
Keep slight right
10.2 mi · 12 min
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19
Take the exit slight right toward CT 66: Willimantic, Middletown
1259 ft · 36 sec
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20
Keep slight left to continue on CT 66 East: Hebron, Willimantic
54 m · 12 sec
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21
Turn left onto East Hampton Road
158 m · 7 sec · East Hampton Road
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22
Continue on Hebron Road
2.2 mi · 3 min · Hebron Road
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23
Continue on West Main Street
3 mi · 3 min · West Main Street
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24
Continue on Main Street
1.4 mi · 2 min · Main Street
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25
Continue on Middletown Road
8.1 mi · 9 min · Middletown Road
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26
Take the exit slight right toward CT 195: University of Connecticut, Storrs
1173 ft · 29 sec
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27
Keep slight left to continue on South Frontage Road
1.3 km · 2 min · South Frontage Road
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28
Turn right onto Storrs Road
787 ft · 13 sec · Storrs Road
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29
Continue on Jackson Street
2559 ft · 46 sec · Jackson Street
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30
Turn left onto Ash Street
2678 ft · 2 min · Ash Street
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31
At the end of the road, turn left onto Main Street
30 m · 3 sec · Main Street
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32
Continue on Main Street
1137 ft · 32 sec · Main Street
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33
Continue on Bricktop Road
1.3 km · 2 min · Bricktop Road
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34
Continue on Brick Top Road
977 ft · 28 sec · Brick Top Road
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35
Continue on Bricktop Road
1.1 km · 1 min · Bricktop Road
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36
Continue on North Road
1.3 km · 2 min · North Road
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37
Turn left onto Scotland Road
60 m · 4 sec · Scotland Road
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38
Arrive at your destination
0 m · 1 sec · Scotland Road
Car Route Details
A richer read on the saved driving route between Fairfield and Windham.
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
Continue on Wilbur Cross Parkway
27 mi · 00h 34m
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.
Forecast cards are syncing for this route.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Fairfield to Windham?
The road trip is about 88.5 miles (142.4 km) and usually takes 01h 55m 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?
Middlefield is a useful midpoint, sitting about 44.2 miles from Fairfield and 44.3 miles from Windham.
How much longer is the road route than the straight-line distance?
The direct path is about 69.1 miles (111.2 km), while the road route adds roughly 19.4 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 2:40 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $12.31 one way or $24.62 round trip. Estimated CO2 is about 27.7 kg one way.
Stop Ideas Near Middlefield
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 Middlefield.
Meriden Transit Center
Wallingford station
Berlin
Hartford Union Station
Flight Path Map
This map shows the direct air route between Fairfield and Windham. Straight-line distance: 69.12 mi (111.24 km).
#1 Fairfield
Town in Connecticut, United States of America
| Population | 62,215 |
| Coordinates | 41.1412100, -73.2637300 |
| Altitude | 10 |
| Country | United States |
#2 Windham
Town in Connecticut
| Population | 24,463 |
| Coordinates | 41.6998200, -72.1570200 |
| Altitude | 86 |
| Country | United States |
End: Windham (-72.15702, 41.69982)
Estimated Travel Time
Distance: 142 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 56m |
| 40 mph (64.37 km/h) | 02h 12m |
| 50 mph (80.47 km/h) | 01h 46m |
| 60 mph (96.56 km/h) | 01h 28m |
| 70 mph (112.65 km/h) | 01h 15m |
| 80 mph (129 km/h) | 01h 06m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $12.31 | $24.62 |
| Mid-grade | $4.46 | $13.91 | $27.81 |
| Premium | $4.86 | $15.16 | $30.31 |
| Diesel | $6.00 | $18.71 | $37.42 |
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.