How far is Fairfield, CT from Middlebury, CT?
The driving distance from Fairfield, CT to Middlebury, CT is about 36.1 miles (58.1 km), with a travel time of about 00h 49m by car.
- The straight-line flight distance is about 27.7 miles (44.5 km).
- For a round trip, plan for roughly 01h 39m 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 49m.
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.
City in New Haven County, Connecticut, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Partly Sunny then Slight Chance Rain Showers
Slight Chance Rain Showers then Mostly Cloudy
Driving Route Map
The map below follows the saved road route between Fairfield and Middlebury.
Turn-by-Turn Driving Directions
Step-by-step road directions between Fairfield and Middlebury.
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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
21.4 mi · 27 min
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8
Take the exit slight right toward CT 63: South Main Street
846 ft · 29 sec
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9
Turn left onto South Main Street
1518 ft · 34 sec · South Main Street
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10
Turn left onto Maple Street
95 m · 10 sec · Maple Street
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11
Turn right onto Water Street
2240 ft · 1 min · Water Street
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12
Turn right onto Church Street
1.6 mi · 3 min · Church Street
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13
Continue on Straits Turnpike
1.5 km · 2 min · Straits Turnpike
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14
Turn left onto Whittemore Road
1.9 mi · 3 min · Whittemore Road
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15
Continue on Whittemore Road
1.1 km · 1 min · Whittemore Road
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16
Turn slight right onto Middlebury Store Road
37 m · 5 sec · Middlebury Store Road
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17
Arrive at your destination
0 m · 1 sec · Middlebury Store Road
Car Route Details
A richer read on the saved driving route between Fairfield and Middlebury.
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 North
Keep slight right to continue on CT 8 North: Waterbury, New Haven
21.4 mi · 00h 27m
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.
Partly Sunny then Slight Chance Rain Showers leaving Fairfield and Slight Chance Rain Showers then Mostly Cloudy near Middlebury.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Fairfield to Middlebury?
The road trip is about 36.1 miles (58.1 km) and usually takes 00h 49m 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?
Derby is a useful midpoint, sitting about 18 miles from Fairfield and 18 miles from Middlebury.
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 8.4 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 4:50 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $5.01 one way or $10.02 round trip. Estimated CO2 is about 11.3 kg one way.
What should you check before leaving?
Before you leave, expect Partly Sunny then Slight Chance Rain Showers around Fairfield and Slight Chance Rain Showers then Mostly Cloudy near Middlebury.
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 Fairfield and Middlebury. Straight-line distance: 27.63 mi (44.47 km).
#1 Fairfield
Town in Connecticut, United States of America
| Population | 62,215 |
| Coordinates | 41.1412100, -73.2637300 |
| Altitude | 10 |
| Country | United States |
#2 Middlebury
Town in Connecticut
| Population | 7,829 |
| Coordinates | 41.5278700, -73.1276100 |
| Altitude | 212 |
| Country | United States |
End: Middlebury (-73.12761, 41.52787)
Estimated Travel Time
Distance: 58 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 12m |
| 40 mph (64.37 km/h) | 00h 54m |
| 50 mph (80.47 km/h) | 00h 43m |
| 60 mph (96.56 km/h) | 00h 36m |
| 70 mph (112.65 km/h) | 00h 30m |
| 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 | $5.01 | $10.02 |
| Mid-grade | $4.46 | $5.66 | $11.32 |
| Premium | $4.86 | $6.17 | $12.34 |
| Diesel | $6.00 | $7.62 | $15.23 |
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.