How far is Middlebury, CT from Fairfield, CT?
The driving distance from Middlebury, CT to Fairfield, CT is about 36.8 miles (59.2 km), with a travel time of about 00h 44m by car.
- The straight-line flight distance is about 27.7 miles (44.5 km).
- For a round trip, plan for roughly 01h 29m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 7:00 AM to 7:00 PM EDT.
Reverse, save, or send this route
This is an easy same-day return drive. Copy the route link, send it to another device, or print a clean version before you head out.
This is an easy same-day return drive.
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 44m.
This is a short drive, so your comfort window is wide. Traffic and current weather matter more than the clock.
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.
City in New Haven County, Connecticut, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Slight Chance Rain Showers then Mostly Cloudy
Partly Sunny then Slight Chance Rain Showers
Driving Route Map
The map below follows the saved road route between Middlebury and Fairfield.
Turn-by-Turn Driving Directions
Step-by-step road directions between Middlebury and Fairfield.
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1
Start on Middlebury Store Road
37 m · 6 sec · Middlebury Store Road
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2
Turn slight left onto Whittemore Road
1.1 km · 1 min · Whittemore Road
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3
Continue on Whittemore Road
1.9 mi · 3 min · Whittemore Road
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4
Turn right onto Straits Turnpike
1.5 km · 1 min · Straits Turnpike
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5
Continue on Church Street
1.6 mi · 3 min · Church Street
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6
Turn right onto Meadow Street
1 km · 59 sec · Meadow Street
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7
Enter the roundabout and take exit 2 toward Cherry Street
28 m · 2 sec · Cherry Street
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8
Exit the roundabout onto Cherry Street
1047 ft · 20 sec · Cherry Street
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9
Continue on Cherry Street
1432 ft · 29 sec · Cherry Street
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10
Take the ramp right toward CT 8 South: Bridgeport
866 ft · 21 sec
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11
Merge slight left
24.7 mi · 31 min
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12
Keep slight right to continue on I 95 South: New York City
1719 ft · 42 sec
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13
Merge slight left
4.2 mi · 6 min
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14
Take the exit slight right toward Mill Plain Road
1525 ft · 42 sec
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15
Turn left onto Mill Plain Road
1655 ft · 39 sec · Mill Plain Road
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16
Turn right onto Post Road
57 m · 3 sec · Post Road
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17
Arrive at your destination
0 m · 1 sec · Post Road
Car Route Details
A richer read on the saved driving route between Middlebury and Fairfield.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
CT 8 South
Merge slight left
24.7 mi · 00h 31m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A short regional drive
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
Slight Chance Rain Showers then Mostly Cloudy leaving Middlebury and Partly Sunny then Slight Chance Rain Showers near Fairfield.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Middlebury to Fairfield?
The road trip is about 36.8 miles (59.2 km) and usually takes 00h 44m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
What is the halfway point on this route?
Derby is a useful midpoint, sitting about 18.1 miles from Middlebury and 18.7 miles from Fairfield.
How much longer is the road route than the straight-line distance?
The direct path is about 27.7 miles (44.5 km), while the road route adds roughly 9.1 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 7:00 AM to 7:00 PM EDT. If you want a more comfortable same-day return, try to leave by 7:00 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $5.13 one way or $10.26 round trip. Estimated CO2 is about 11.6 kg one way.
What should you check before leaving?
Before you leave, expect Slight Chance Rain Showers then Mostly Cloudy around Middlebury and Partly Sunny then Slight Chance Rain Showers near Fairfield.
Stop Ideas Near Derby
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 Derby.
Union Station
Bridgeport
Wallingford station
Meriden Transit Center
Flight Path Map
This map shows the direct air route between Middlebury and Fairfield. Straight-line distance: 27.63 mi (44.47 km).
#1 Middlebury
Town in Connecticut
| Population | 7,829 |
| Coordinates | 41.5278700, -73.1276100 |
| Altitude | 212 |
| 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: 59 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 13m |
| 40 mph (64.37 km/h) | 00h 55m |
| 50 mph (80.47 km/h) | 00h 44m |
| 60 mph (96.56 km/h) | 00h 36m |
| 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 | $5.13 | $10.26 |
| Mid-grade | $4.46 | $5.79 | $11.59 |
| Premium | $4.86 | $6.32 | $12.63 |
| Diesel | $6.00 | $7.80 | $15.59 |
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.