Bridgeport, CT to South Windham, CT is 82.6 miles and takes about 1 hour 47 minutes via Wilbur Cross Parkway and I-91, with a fuel budget near $13 and enough daylight to finish in a day. This trip stays within Connecticut, moving from the Northeast region to another part of the Northeast. It's a straightforward drive, mostly on highways, making it a convenient option for getting from one point to another in the state. You'll find it’s a practical choice if you're looking for an efficient way to travel between these two locations without extensive planning.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
41.3 miles from Bridgeport, CT
A natural place for your longest stop of the day
, about 52m into the drive
.
Main Roads
Road
Distance
Duration
Wilbur Cross Parkway
27 mi
33m
I 91
13.6 mi
15m
CT 2
10.6 mi
12m
Middletown Road
6.8 mi
7m
CT 8
4.5 mi
5m
Merritt Parkway
3 mi
4m
West Main Street
3 mi
3m
Windham Road
2.8 mi
5m
Longest stretch:
Wilbur Cross Parkway
— 27 mi, about 33m
Turn-by-Turn Driving Directions
Step-by-step road directions between Bridgeport, CT and South Windham, CT.
1
Start on CT 130
0.3 mi·32 sec·Fairfield Avenue
2
Take the ramp
0.2 mi·29 sec
Toward CT 8, CT 25 North: Trumbull, Waterbury
3
Merge onto CT 8; CT 25
2.7 mi·2 min·CT 8; CT 25
Use the straight / right lanes.
4
Keep slight right at fork onto CT 8
1.8 mi·2 min·CT 8
Toward CT 8 North: Waterbury, New Haven
5
Take the exit
0.7 mi·1 min
Exit 6Toward CT 15 North: Merritt Parkway, New HavenUse the slight right lane.
6
Merge onto CT 15
3.0 mi·4 min·Merritt Parkway
Use the straight / slight right lanes.
7
Continue on CT 15
27 mi·33 min·Wilbur Cross Parkway
Use the straight / slight right lanes.
8
Take the exit
0.3 mi·38 sec
Exit 65AToward I 91 North, CT 66 East: Hartford, MiddletownUse the slight right lane.
9
Merge onto I 91
14 mi·15 min·I 91
Use the straight / slight right lanes.
10
Take the exit
0.2 mi·23 sec
Exit 25-26Toward CT 3 North: Glastonbury, Old WethersfieldUse the slight right lane.
11
Keep slight left at fork
0.3 mi·36 sec
Exit 25Toward CT 3 North: GlastonburyUse the straight / slight right lanes.
12
Merge onto CT 3
1.9 mi·2 min·CT 3
Use the straight / slight right lanes.
13
Keep slight right at fork
0.3 mi·34 sec
Exit 13 CToward CT 2 East: NorwichUse the slight right lane.
14
Merge onto CT 2
0.4 mi·33 sec·CT 2
15
Keep slight right at fork onto CT 2
10 mi·11 min·CT 2
Use the straight / slight right lanes.
16
Take the exit
0.2 mi·36 sec
Exit 15Toward CT 66: Willimantic, MiddletownUse the slight right lane.
17
Keep slight left at fork
178 ft·11 sec
Toward CT 66 East: Hebron, Willimantic
18
Turn left onto CT 66
520 ft·6 sec·East Hampton Road
19
Continue on CT 66
2.2 mi·2 min·Hebron Road
20
Continue on CT 66
3.0 mi·3 min·West Main Street
21
Continue on CT 66
1.4 mi·1 min·Main Street
22
Continue on CT 66
6.8 mi·7 min·Middletown Road
Use the straight / right lanes.
23
Take the exit
0.2 mi·41 sec
Exit 89Toward CT 32: Stafford Springs, Willimantic
24
Turn right onto CT 32
0.7 mi·1 min·Main Street
25
Turn left onto West Avenue
453 ft·12 sec·West Avenue
26
Turn right onto Valley Street
1.3 mi·3 min·Valley Street
27
Turn right onto Jackson Street
0.1 mi·16 sec·Jackson Street
28
Continue on South Street
0.1 mi·17 sec·South Street
29
Turn left onto CT 32
0.3 mi·37 sec·Pleasant Street
30
Continue on CT 32
2.8 mi·5 min·Windham Road
31
Turn right onto Main Street
311 ft·15 sec·Main Street
32
Turn right
50 ft·5 sec
33
Turn left
94 ft·6 sec
34
Arrive at destination
Trip Plan
Given the short 1 hour 47 minute duration, you have a lot of flexibility with this route. Leaving Bridgeport, CT anytime in the morning should get you to South Windham with plenty of daylight to spare. With a fuel cost estimated at $13, it's wise to ensure your tank is full before you depart, as there are no specified stops for rest or refueling. The longest continuous stretch on the Wilbur Cross Parkway is 27 miles, so plan your own breaks accordingly before or after that segment.
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 41.3 miles from Bridgeport, CT, or about 52m into the drive.
The longest continuous stretch on this route runs about 27 miles.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 18 miles or 23m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 41.3 miles or 52m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 27m
Traffic, exits, and arrival timing usually matter more near South Windham, CT than in the middle of the route.
Before You Leave
+
Open the route before leaving Bridgeport, CT so your first major turns are already loaded.
Day 1
Settle into the route from Bridgeport, CT
This is one driving day of about 82.6 miles and 1h 47m.
Your first comfortable stop window is around 18 miles from Bridgeport, CT.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on Wilbur Cross Parkway for about 27 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 25
5 decision points cluster between mile 5 and 52.1 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
8
5 mi into trip|~6m in
Take the exit toward CT 15 North: Merritt Parkway, New Haven
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 6
Toward CT 15 North: Merritt Parkway, New Haven
8
35.7 mi into trip|~45m in
Take the exit toward I 91 North, CT 66 East: Hartford, Middletown
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 65A
Toward I 91 North, CT 66 East: Hartford, Middle...
8
49.7 mi into trip|~1h 1m in
Take the exit toward CT 3 North: Glastonbury, Old Wethersfield
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 25-26
Toward CT 3 North: Glastonbury, Old Wethersfiel...
9
49.9 mi into trip|~1h 2m in
Keep slight left at fork toward CT 3 North: Glastonbury
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Exit 25
Toward CT 3 North: Glastonbury
8
52.1 mi into trip|~1h 5m in
Keep slight right at fork toward CT 2 East: Norwich
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Exit 13 C
Toward CT 2 East: Norwich
Fuel & Cost
Regular Gas
$13.30 one way
$26.59 round trip
$4.09/gal25.4 MPG avg29 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.50
$14.63
$29.26
premium
$4.86
$15.82
$31.64
diesel
$5.61
$18.24
$36.47
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$13
Meals
$25–$50
Total
$38–$63
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 28.9 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $9 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
24.8
0
$8.67
$3.96
Efficient EV
20.7
0
$7.23
$3.30
EV Truck/SUV
33
0
$11.56
$5.29
Gas CO2
29 kg
EV CO2
10 kg (66% less)
This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive.
Forecast as of Apr 16, 2026
Origin
Bridgeport, CT
Morning
in Bridgeport on Tuesday
Local time
7:00 AM
EDT
Current temp
44°F
Unavailable
Live forecast
Destination
South Windham, CT
Morning
in South Windham on Tuesday
Local time
7:00 AM
EDT
Current temp
56°F
Unavailable
Live forecast
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
12 degrees warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
1h 47m on the road
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
National Parks Near This Route
Worth a detour if your schedule allows.
Weir Farm National Historical Park
National Historical Park
Visit the home and studio of America's most beloved Impressionist, J. Alden Weir, and walk in the footsteps of generations of world-class artists. Set amidst more than 60 acres of painterly woods, fie...
14 mi from route
~36 min detour
Free
near mile 2.8
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This drive is predominantly highway, with 73% of the 82.6 miles covered on higher-speed roads like Wilbur Cross Parkway and I-91. You'll experience a longest stretch of 27 miles on the Wilbur Cross Parkway before transitioning to other routes. Expect a consistent flow of traffic with frequent exits as you make your way across Connecticut, typical for a route of this nature.
73% highway — fuel and pacing are the main things to plan.
34 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 27 mi on Wilbur Cross Parkway.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on Wilbur Cross Parkway and I 91. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 5 miles in.
Driving Effort10/10
Demanding - stay alert through the decision-heavy sections
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 82.6 miles you will encounter 25 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
Where does it get tricky?
The main spots that need attention: at 5 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 35.7 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 49.7 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Bridgeport, CT and South Windham, CT, road signs point toward New Haven, Middletown, Old Wethersfield and Willimantic.
New Haven
5 mi in|~6m
Middletown
35.7 mi in|~45m
Old Wethersfield
49.7 mi in|~1h 1m
Willimantic
63.2 mi in|~1h 19m
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 1h 47m. Total distance: 82.6 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 47m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (73%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 27 miles on Wilbur Cross Parkway. The full list of main roads is in the Roads section above.
Yes — we found about 4 rest areas or service plazas within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at South Windham, CT before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Yes. At under 2 hours behind the wheel, this works well for families — plan one quick stop if you have younger kids.
The main spots that need attention: at 5 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 35.7 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 49.7 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — Weir Farm National Historical Park. See the National Parks section for detour distances and tips on detours.
Yes. A round trip is manageable in a single day if you plan a break at South Windham, CT before heading back.
