How far is Bridgeport, CT from Middlebury, CT?
The driving distance from Bridgeport, CT to Middlebury, CT is about 30.8 miles (49.5 km), with a travel time of about 00h 42m by car.
- The straight-line flight distance is about 24.3 miles (39.1 km).
- For a round trip, plan for roughly 01h 24m 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 42m.
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.
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Bridgeport and Middlebury.
Turn-by-Turn Driving Directions
Step-by-step road directions between Bridgeport and Middlebury.
-
1
Start on Fairfield Avenue
1432 ft · 33 sec · Fairfield Avenue
-
2
Take the ramp right toward CT 8, CT 25 North: Trumbull, Waterbury
1207 ft · 30 sec
-
3
Merge slight left
2.7 mi · 3 min
-
4
Keep slight right to continue on CT 8 North: Waterbury, New Haven
21.4 mi · 27 min
-
5
Take the exit slight right toward CT 63: South Main Street
846 ft · 29 sec
-
6
Turn left onto South Main Street
1518 ft · 34 sec · South Main Street
-
7
Turn left onto Maple Street
95 m · 10 sec · Maple Street
-
8
Turn right onto Water Street
2240 ft · 1 min · Water Street
-
9
Turn right onto Church Street
1.6 mi · 3 min · Church Street
-
10
Continue on Straits Turnpike
1.5 km · 2 min · Straits Turnpike
-
11
Turn left onto Whittemore Road
1.9 mi · 3 min · Whittemore Road
-
12
Continue on Whittemore Road
1.1 km · 1 min · Whittemore Road
-
13
Turn slight right onto Middlebury Store Road
37 m · 5 sec · Middlebury Store Road
-
14
Arrive at your destination
0 m · 1 sec · Middlebury Store Road
Car Route Details
A richer read on the saved driving route between Bridgeport 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 short regional drive
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
Mostly Sunny near Middlebury.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Bridgeport to Middlebury?
The road trip is about 30.8 miles (49.5 km) and usually takes 00h 42m 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?
Ansonia is a useful midpoint, sitting about 15.3 miles from Bridgeport and 15.3 miles from Middlebury.
How much longer is the road route than the straight-line distance?
The direct path is about 24.3 miles (39.1 km), while the road route adds roughly 6.5 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 7:06 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $4.30 one way or $8.60 round trip. Estimated CO2 is about 9.7 kg one way.
What should you check before leaving?
Before arriving, the latest forecast around Middlebury is Mostly Sunny.
Stop Ideas Near Ansonia
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 Ansonia.
Union Station
Bridgeport
Wallingford station
Meriden Transit Center
Flight Path Map
This map shows the direct air route between Bridgeport and Middlebury. Straight-line distance: 24.3 mi (39.11 km).
#1 Bridgeport
The second most populous city in Connecticut.
| Population | 143,525 |
| Coordinates | 41.1792300, -73.1894500 |
| Altitude | 1 |
| 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: 49 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 01m |
| 40 mph (64.37 km/h) | 00h 46m |
| 50 mph (80.47 km/h) | 00h 36m |
| 60 mph (96.56 km/h) | 00h 30m |
| 70 mph (112.65 km/h) | 00h 26m |
| 80 mph (129 km/h) | 00h 23m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $4.30 | $8.60 |
| Mid-grade | $4.46 | $4.86 | $9.72 |
| Premium | $4.86 | $5.30 | $10.59 |
| Diesel | $6.00 | $6.54 | $13.07 |
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.