How far is Bridgeport, CT from South Windham, CT?
The driving distance from Bridgeport, CT to South Windham, CT is about 82.6 miles (132.9 km), with a travel time of about 01h 47m by car.
- The straight-line flight distance is about 63.1 miles (101.6 km).
- For a round trip, plan for roughly 03h 34m 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 47m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
This departure sits inside the recommended comfort window for the route.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Town in Connecticut
Route Weather Snapshot
Check the forecast at both ends before you head out.
Partly Sunny
Mostly Cloudy
Driving Route Map
The map below follows the saved road route between Bridgeport and South Windham.
Turn-by-Turn Driving Directions
Step-by-step road directions between Bridgeport and South Windham.
-
1
Start on Fairfield Avenue
1432 ft · 33 sec · Fairfield Avenue
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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
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4
Keep slight right to continue on CT 8 North: Waterbury, New Haven
1.8 mi · 2 min
-
5
Take the exit slight right toward CT 15 North: Merritt Parkway, New Haven
1.2 km · 2 min
-
6
Merge slight left onto Merritt Parkway
3 mi · 4 min · Merritt Parkway
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7
Continue on Wilbur Cross Parkway
27 mi · 34 min · Wilbur Cross Parkway
-
8
Take the exit slight right toward I 91 North, CT 66 East: Hartford, Middletown
1815 ft · 39 sec
-
9
Merge slight left
13.6 mi · 16 min
-
10
Take the exit slight right toward CT 3 North: Glastonbury, Old Wethersfield
952 ft · 23 sec
-
11
Keep slight left to continue on CT 3 North: Glastonbury
1515 ft · 37 sec
-
12
Merge slight left
1.9 mi · 3 min
-
13
Keep slight right to continue on CT 2 East: Norwich
1622 ft · 34 sec
-
14
Merge slight left
2125 ft · 33 sec
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15
Keep slight right
10.2 mi · 12 min
-
16
Take the exit slight right toward CT 66: Willimantic, Middletown
1259 ft · 36 sec
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17
Keep slight left to continue on CT 66 East: Hebron, Willimantic
54 m · 12 sec
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18
Turn left onto East Hampton Road
158 m · 7 sec · East Hampton Road
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19
Continue on Hebron Road
2.2 mi · 3 min · Hebron Road
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20
Continue on West Main Street
3 mi · 3 min · West Main Street
-
21
Continue on Main Street
1.4 mi · 2 min · Main Street
-
22
Continue on Middletown Road
6.8 mi · 8 min · Middletown Road
-
23
Take the exit slight right toward CT 32: Stafford Springs, Willimantic
1147 ft · 42 sec
-
24
Turn right onto Main Street
1.2 km · 1 min · Main Street
-
25
Turn left onto West Avenue
138 m · 13 sec · West Avenue
-
26
Turn right onto Valley Street
1.3 mi · 3 min · Valley Street
-
27
Turn right onto Jackson Street
750 ft · 17 sec · Jackson Street
-
28
Continue on South Street
643 ft · 17 sec · South Street
-
29
Turn left onto Pleasant Street
1514 ft · 37 sec · Pleasant Street
-
30
Continue on Windham Road
2.8 mi · 5 min · Windham Road
-
31
Turn right onto Main Street
95 m · 16 sec · Main Street
-
32
Turn right
15 m · 5 sec
-
33
Turn left
29 m · 7 sec
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34
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Bridgeport and South Windham.
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.
Wilbur Cross Parkway
Continue on Wilbur Cross Parkway
27 mi · 00h 34m
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 leaving Bridgeport and Mostly Cloudy near South Windham.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Bridgeport to South Windham?
The road trip is about 82.6 miles (132.9 km) and usually takes 01h 47m 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?
Berlin is a useful midpoint, sitting about 41.3 miles from Bridgeport and 41.3 miles from South Windham.
How much longer is the road route than the straight-line distance?
The direct path is about 63.1 miles (101.6 km), while the road route adds roughly 19.5 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 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 2:56 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $11.48 one way or $22.96 round trip. Estimated CO2 is about 25.9 kg one way.
What should you check before leaving?
Before you leave, expect Partly Sunny around Bridgeport and Mostly Cloudy near South Windham.
Stop Ideas Near Berlin
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 Berlin.
Berlin
Meriden Transit Center
Hartford Union Station
Wallingford station
Flight Path Map
This map shows the direct air route between Bridgeport and South Windham. Straight-line distance: 63.1 mi (101.55 km).
#1 Bridgeport
The second most populous city in Connecticut.
| Population | 143,525 |
| Coordinates | 41.1792300, -73.1894500 |
| Altitude | 1 |
| Country | United States |
#2 South Windham
Village in the United States
| Population | 1,421 |
| Coordinates | 41.6795400, -72.1703600 |
| Altitude | 50 |
| Country | United States |
End: South Windham (-72.17036, 41.67954)
Estimated Travel Time
Distance: 133 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 45m |
| 40 mph (64.37 km/h) | 02h 03m |
| 50 mph (80.47 km/h) | 01h 39m |
| 60 mph (96.56 km/h) | 01h 22m |
| 70 mph (112.65 km/h) | 01h 10m |
| 80 mph (129 km/h) | 01h 01m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $11.48 | $22.96 |
| Mid-grade | $4.46 | $12.97 | $25.94 |
| Premium | $4.86 | $14.14 | $28.27 |
| Diesel | $6.00 | $17.45 | $34.90 |
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 18, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.