How far is Winchester Center, CT from Bridgeport, CT?
The driving distance from Winchester Center, CT to Bridgeport, CT is about 57.6 miles (92.7 km), with a travel time of about 01h 03m by car.
- The straight-line flight distance is about 49.9 miles (80.3 km).
- For a round trip, plan for roughly 02h 06m 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 03m.
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.
The second most populous city in Connecticut.
Route Weather Snapshot
Check the forecast at both ends before you head out.
Chance Rain Showers then Mostly Sunny
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Winchester Center and Bridgeport.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winchester Center and Bridgeport.
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1
Start on West Road
23 m · 8 sec · West Road
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2
Turn right onto Newfield Road
5.9 mi · 15 min · Newfield Road
-
3
Continue on Main Street
2654 ft · 52 sec · Main Street
-
4
Turn left onto East Elm Street
2550 ft · 48 sec · East Elm Street
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5
Turn right onto Columbus Street
699 ft · 16 sec · Columbus Street
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6
Continue on CT 8 South: Waterbury
1026 ft · 25 sec
-
7
Merge slight left
48 mi · 59 min
-
8
Take the exit slight right toward Main Street, Washington Avenue
719 ft · 18 sec
-
9
Continue on Main Street, Washington Avenue
111 m · 9 sec
-
10
Keep slight left to continue on Main Street South, East Washington Avenue
1381 ft · 34 sec
-
11
Turn straight onto Main Street
2720 ft · 1 min · Main Street
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12
Turn right onto Fairfield Avenue
1 m · 1 sec · Fairfield Avenue
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13
Arrive at your destination
0 m · 1 sec · Fairfield Avenue
Car Route Details
A richer read on the saved driving route between Winchester Center and Bridgeport.
Straightforward drive
The saved road route has a manageable number of maneuvers and should be easy to follow with normal attention to signs.
CT 8 South
Merge slight left
48 mi · 00h 59m
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.
Chance Rain Showers then Mostly Sunny leaving Winchester Center and Mostly Sunny near Bridgeport.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winchester Center to Bridgeport?
The road trip is about 57.6 miles (92.7 km) and usually takes 01h 03m 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?
Waterbury is a useful midpoint, sitting about 28.1 miles from Winchester Center and 29.5 miles from Bridgeport.
How much longer is the road route than the straight-line distance?
The direct path is about 49.9 miles (80.3 km), while the road route adds roughly 7.7 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 4:24 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $8.01 one way or $16.02 round trip. Estimated CO2 is about 18 kg one way.
What should you check before leaving?
Before you leave, expect Chance Rain Showers then Mostly Sunny around Winchester Center and Mostly Sunny near Bridgeport.
Stop Ideas Near Waterbury
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 Waterbury.
Meriden Transit Center
Wallingford station
Berlin
Union Station
Flight Path Map
This map shows the direct air route between Winchester Center and Bridgeport. Straight-line distance: 49.89 mi (80.29 km).
#1 Winchester Center
Town in Litchfield County, Connecticut, United States
| Population | 10,830 |
| Coordinates | 41.9001000, -73.1348300 |
| Altitude | 404 |
| Country | United States |
#2 Bridgeport
The second most populous city in Connecticut.
| Population | 143,525 |
| Coordinates | 41.1792300, -73.1894500 |
| Altitude | 1 |
| Country | United States |
End: Main Street (-73.189437, 41.179239)
Estimated Travel Time
Distance: 93 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 55m |
| 40 mph (64.37 km/h) | 01h 26m |
| 50 mph (80.47 km/h) | 01h 09m |
| 60 mph (96.56 km/h) | 00h 57m |
| 70 mph (112.65 km/h) | 00h 49m |
| 80 mph (129 km/h) | 00h 43m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $8.01 | $16.02 |
| Mid-grade | $4.46 | $9.05 | $18.10 |
| Premium | $4.86 | $9.86 | $19.72 |
| Diesel | $6.00 | $12.17 | $24.35 |
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 · May 30, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.