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Trip from Windham, CT to Fairfield, CT

Drive Time

1h 56m

Distance

89.7 mi

144 km

Drive Score

8/10

Great drive

Same Day?

Yes, doable

Fuel Cost

$14

one way

EV Charging

None

0 DC fast

Best Time to Leave

Save up to 26 min
4 AM
1h 48m ★
6 AM
1h 57m
8 AM
2h 14m
10 AM
2h 3m
12 PM
2h 1m
3 PM
2h 3m
5 PM
2h 13m
8 PM
1h 52m

Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.

Best Time Drive vs Fly
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Downtown Fairfield, CT, CT

Fairfield, CT

MART PRODUCTION

Trip Overview

The drive from Windham, CT to Fairfield, CT covers 89.7 miles and takes about 1h 56m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.

The route leans on CT 15, I 91, CT 2 for much of the mileage, and the overall profile is highway-focused drive. The longest uninterrupted segment is about 29.8 miles on CT 15. At current regular gas prices, budget about $14.36 one way before food or hotel costs.

Trip Pace

Same-day drive is realistic

A same-day return is realistic if you keep stops short.

Break Rhythm

0 planned breaks

A short stop every 2 to 3 hours is enough for this drive.

Midpoint

44.8 miles from Windham, CT

A natural place for your longest stop of the day , about 59m into the drive .

Drive Character

This is a 1h 56m highway drive covering 89.7 miles, with most of the trip on CT 15 and I 91. The longest continuous stretch is about 29.8 miles on CT 15.

Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 31 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
CT 15 is the longest continuous segment at about 29.8 miles.

How Hard Is This Drive?

This is a straightforward highway drive that stays mostly on CT 15 and I 91. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 31.4 miles in.

Route Complexity 10/10

High effort - long or complex enough to need steady focus all day

This is a demanding drive. With 22 significant decision points across 89.7 miles, you will need to stay alert — especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.

Where does it get tricky?

The main spots that need attention: at 31.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here; at 48.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here; at 48.7 miles: Highway fork - watch signs carefully. Lane positioning matters here.

Critical Maneuvers

5 of 22 key points

These are the spots where you need to pay the most attention. Preview them before you drive.

7
31.4 mi into trip | ~41m in

Take the exit toward CT 3 South: Wethersfield

Exit ramp - move to the correct lane early. Lane positioning matters here

Use the slight right lane. Exit 4 Toward CT 3 South: Wethersfield
7
48.4 mi into trip | ~1h 3m in

Take the exit toward CT 15 South

Exit ramp - move to the correct lane early. Lane positioning matters here

Use the slight right lane. Exit 17 Toward CT 15 South
7
48.7 mi into trip | ~1h 3m in

Keep slight left at fork toward CT 15 South

Highway fork - watch signs carefully. Lane positioning matters here

Use the straight / slight right lanes. Toward CT 15 South
8
78.6 mi into trip | ~1h 41m in

Take the exit toward CT 8, CT 108: Bridgeport, Waterbury

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 34 Toward CT 8, CT 108: Bridgeport, Waterbury
7
79.3 mi into trip | ~1h 42m in

Keep slight left at fork toward CT 8 South: Bridgeport

Highway fork - watch signs carefully. Lane positioning matters here

Use the slight left lane. Toward CT 8 South: Bridgeport

Towns Along This Route

On the drive from Windham, CT to Fairfield, CT, road signs begin pointing toward Waterbury along the way.

Waterbury

78.6 mi in | ~1h 41m

Main Roads

Road Distance Duration
CT 15 29.8 mi 37m
I 91 13.3 mi 15m
CT 2 11 mi 12m
US 6 5 mi 6m
Middletown Road 5 mi 5m
CT 8 4.5 mi 5m
I 95 4.2 mi 5m
West Main Street 3 mi 3m
Longest stretch: CT 15 — 29.8 mi, about 37m

Turn-by-Turn Driving Directions

Step-by-step road directions between Windham, CT and Fairfield, CT.

1

Start on CT 14

200 ft · 6 sec · Scotland Road
2

Turn right onto CT 14; CT 203

0.8 mi · 1 min · North Road
3

Continue on CT 14

0.1 mi · 15 sec · Bricktop Road
4

Turn right onto Tuckie Road

1.9 mi · 4 min · Tuckie Road
5

At end of road, turn right onto CT 66

290 ft · 5 sec · Boston Post Road
6

Take the ramp

0.6 mi · 1 min
7

Merge onto US 6

5.0 mi · 6 min · US 6
8

Keep slight left at fork onto CT 66

5.0 mi · 5 min · Middletown Road
Use the straight / right lanes.
9

Continue on CT 66

1.4 mi · 1 min · Main Street
Use the straight / right lanes.
10

Continue on CT 66

3.0 mi · 3 min · West Main Street
Use the left / straight / right lanes.
11

Continue on CT 66

2.2 mi · 2 min · Hebron Road
12

Take the exit

0.2 mi · 24 sec
Toward CT 2 West: Hartford
13

Merge onto CT 2

11 mi · 12 min · CT 2
Use the straight / slight right lanes.
14

Take the exit

0.6 mi · 1 min
Exit 4 Toward CT 3 South: Wethersfield Use the slight right lane.
15

Continue on this road

0.2 mi · 29 sec · this road
Exit 5D Toward CT 3 South: Wethersfield
16

Continue on CT 3

2.2 mi · 3 min · CT 3
Use the straight / slight right lanes.
17

Take the exit

0.7 mi · 1 min
Toward I 91 South: New Haven Use the straight / slight left lanes.
18

Merge onto I 91

13 mi · 15 min · I 91
Use the straight / slight right lanes.
19

Take the exit

0.3 mi · 34 sec
Exit 17 Toward CT 15 South Use the slight right lane.
20

Keep slight left at fork

437 ft · 8 sec
Toward CT 15 South Use the straight / slight right lanes.
21

Merge onto CT 15

30 mi · 37 min · CT 15
Use the straight / slight right lanes.
22

Take the exit

0.2 mi · 23 sec
Exit 34 Toward CT 8, CT 108: Bridgeport, Waterbury Use the straight / slight right lanes.
23

Keep slight left at fork

0.4 mi · 48 sec
Toward CT 8 South, CT 108 South: Bridgeport
24

Keep slight left at fork

0.8 mi · 1 min
Toward CT 8 South: Bridgeport Use the slight left lane.
25

Merge onto CT 8

4.5 mi · 5 min · CT 8
26

Keep slight right at fork

0.3 mi · 42 sec
Toward I 95 South: New York City Use the slight right lane.
27

Merge onto I 95

4.2 mi · 5 min · I 95
Use the straight / slight right lanes.
28

Take the exit

0.3 mi · 41 sec
Exit 21 Toward Mill Plain Road Use the slight right lane.
29

Turn left onto Mill Plain Road

0.3 mi · 39 sec · Mill Plain Road
Use the straight / left lanes.
30

Turn right onto US 1

186 ft · 3 sec · Post Road
31

Arrive at destination

US 1

Trip Plan

Morning Departure

Leave by 9 AM and you'll arrive before lunch.

Evening Departure

Even a 4 PM departure gets you there before dark in summer.

You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 44.8 miles from Windham, CT, or about 59m into the drive.
The longest continuous stretch on this route runs about 29.8 miles.

This is a comfortable same-day trip.

Departure

Before you leave

Start with fuel, water, and navigation already sorted so the first hour feels easy.

First stop

Around 80 miles or 1h 43m in

Use this first pause for coffee, a restroom break, and a quick traffic check ahead.

Halfway reset

Around 44.8 miles or 59m in

This is the best place for your longest stop, a real meal, and a full fuel check.

Final approach

Final hour starts around 1h 38m

Traffic, exits, and arrival timing usually matter more near Fairfield, CT than in the middle of the route.

Before You Leave

+

Open the route before leaving Windham, CT so your first major turns are already loaded.

+

Leave with enough water and a charging cable within reach, not packed away.

+

Check your fuel range against the first long segment, especially if you are starting outside city service areas.

Day 1

Settle into the route from Windham, CT

This is one driving day of about 89.7 miles and 1h 56m.

Your first comfortable stop window is around 80 miles from Windham, CT.
This route can stay practical as a one-day drive if traffic stays reasonable.
You may only need one short stretch stop if conditions stay smooth.
The longest stretch is on CT 15 for about 29.8 miles.

Where to Stop

Rest stops, refuel points, and overnight suggestions along this route.

Halfway Point

Midpoint

About 44.8 mi from Windham, CT · 59m into the drive

Downtown Smithtown, NY, NY

Mid-route town

Meal stop

Smithtown, NY

45 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

Smithtown, NY

Fuel and coffee

A short stop after about 80 miles helps settle the day before fatigue starts building.

Smithtown, NY

Meal break

The midpoint is around 44.8 miles from Windham, CT, which is a good place for a longer meal and fuel stop.

Arriving in Fairfield, CT

The final approach into Fairfield, CT usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.

Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Fairfield, CT.

These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.

National Parks Near This Route

Worth a detour if your schedule allows.

Weir Farm National Historical Park

Weir Farm National Historical Park

National Historical Park

Visit the home and studio of America's most beloved Impressionist, J. Alden Weir, and walk in the footsteps of generations of world-class artists. Set amidst more than 60 acres of painterly woods, fie...

13 mi from route ~32 min detour Free near mile 89.7
View on nps.gov

Park data from the National Park Service API. Alerts update every 2 hours.

Fuel & Cost

Regular Gas

$14.36 one way

$28.72 round trip

$4.07/gal 25.4 MPG avg 31 kg CO2
Fuel Type $/gal One Way Round Trip
midgrade $4.46 $15.74 $31.48
premium $4.83 $17.05 $34.10
diesel $5.64 $19.93 $39.86

No toll roads detected on this route.

Estimated Trip Cost (one way, 1 person)

Fuel

$14

Meals

$25–$50

Total

$39–$64

Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.

Estimated CO2 emission: 31.4 kg one way. Prices: EIA weekly data, 2026-04-06.

Driving Electric?

About $9 in charging · 0 stops · 68% less CO2

Vehicle Type kWh Stops DC Fast Home Charge
Average EV 26.9 0 $9.42 $4.31
Efficient EV 22.4 0 $7.85 $3.59
EV Truck/SUV 35.9 0 $12.56 $5.74

Gas CO2

31 kg

EV CO2

10 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.

Forecast data refreshed 3 years ago

Origin

Windham, CT

Afternoon in Windham on Monday

Local time

1:46 PM

EDT

Current temp

82°F

Unavailable

Live forecast

Destination

Fairfield, CT

Afternoon in Fairfield on Monday

Local time

1:46 PM

EDT

Current temp

54°F

Unavailable

Live forecast

Seasonal Notes

Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.

Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.

Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.

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

28 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 56m 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.

Frequently Asked Questions

The drive from Windham, CT to Fairfield, CT covers 89.7 miles and takes about 1h 56m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are CT 15, I 91, CT 2. Most of the drive stays on highways, so watch for ramps and exits.
This is a comfortable same-day trip.
The midpoint is about 44.8 miles from Windham, CT. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $14.36 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.
This is a demanding drive. With 22 significant decision points across 89.7 miles, you will need to stay alert — especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
The main spots that need attention: at 31.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here; at 48.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here; at 48.7 miles: Highway fork - watch signs carefully. Lane positioning matters here.
On the drive from Windham, CT to Fairfield, CT, road signs begin pointing toward Waterbury along the way.

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