Origin
Stamford, CT
Afternoon in Stamford on Saturday
Local time
3:01 PM
EDT
Current temp
44°F
Unavailable
Live forecast
Trip from Stamford, CT to South Windham, CT
Compiled and reviewed by the Trip.ovh planning team at COD Solutions Oy · Last reviewed Apr 18, 2026 · Editorial standards
Drive Time
2h 18m
Distance
104.6 mi
168 km
Drive Score
9/10
Great drive
Same Day?
Yes, doable
Fuel Cost
$17
one way
EV Charging
Unknown
Best Time to Leave
4 AM
2h 9m
★
6 AM
2h 18m
8 AM
2h 37m
10 AM
2h 25m
12 PM
2h 23m
3 PM
2h 26m
5 PM
2h 36m
8 PM
2h 12m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Stamford, CT
Wikimedia Commons
Trip Overview
The drive from Stamford, CT to South Windham, CT covers 104.6 miles and takes about 2h 18m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Wilbur Cross Parkway, I 95, I 91 for much of the mileage, and the overall profile is mostly highway. The longest uninterrupted segment is about 27 miles on Wilbur Cross Parkway. At current regular gas prices, budget about $16.84 one way before food or hotel costs.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
52.3 miles from Stamford, CT
A natural place for your longest stop of the day , about 1h 9m into the drive .
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Wilbur Cross Parkway | 27 mi | 33m |
| I 95 | 20.3 mi | 27m |
| I 91 | 13.6 mi | 15m |
| CT 2 | 10.6 mi | 12m |
| Middletown Road | 6.8 mi | 7m |
| CT 8 | 5 mi | 5m |
| Merritt Parkway | 3 mi | 4m |
| West Main Street | 3 mi | 3m |
Longest stretch:
Wilbur Cross Parkway
— 27 mi, about 33m
Turn-by-Turn Driving Directions
Step-by-step road directions between Stamford, CT and South Windham, CT.
1
Start on Atlantic Street
0.1 mi
·
18 sec
·
Atlantic Street
2
Turn right onto Broad Street
0.3 mi
·
57 sec
·
Broad Street
Use the straight / right lanes.
3
Turn right onto Grove Street
0.3 mi
·
48 sec
·
Grove Street
4
Take the ramp
0.3 mi
·
41 sec
Toward I 95 North: New Haven
5
Merge onto I 95
20 mi
·
27 min
·
I 95
Use the straight / slight right lanes.
6
Take the exit
0.6 mi
·
1 min
Exit 27A
Toward CT 25, CT 8: Trumbull, Waterbury
Use the right lane.
7
Continue on CT 8; CT 25
3.2 mi
·
3 min
·
CT 8; CT 25
Use the straight / right lanes.
8
Keep slight right at fork onto CT 8
1.8 mi
·
2 min
·
CT 8
Toward CT 8 North: Waterbury, New Haven
9
Take the exit
0.7 mi
·
1 min
Exit 6
Toward CT 15 North: Merritt Parkway, New Haven
Use the slight right lane.
10
Merge onto CT 15
3.0 mi
·
4 min
·
Merritt Parkway
Use the straight / slight right lanes.
11
Continue on CT 15
27 mi
·
33 min
·
Wilbur Cross Parkway
Use the straight / slight right lanes.
12
Take the exit
0.3 mi
·
38 sec
Exit 65A
Toward I 91 North, CT 66 East: Hartford, Middletown
Use the slight right lane.
13
Merge onto I 91
14 mi
·
15 min
·
I 91
Use the straight / slight right lanes.
14
Take the exit
0.2 mi
·
23 sec
Exit 25-26
Toward CT 3 North: Glastonbury, Old Wethersfield
Use the slight right lane.
15
Keep slight left at fork
0.3 mi
·
36 sec
Exit 25
Toward CT 3 North: Glastonbury
Use the straight / slight right lanes.
16
Merge onto CT 3
1.9 mi
·
2 min
·
CT 3
Use the straight / slight right lanes.
17
Keep slight right at fork
0.3 mi
·
34 sec
Exit 13 C
Toward CT 2 East: Norwich
Use the slight right lane.
18
Merge onto CT 2
0.4 mi
·
33 sec
·
CT 2
19
Keep slight right at fork onto CT 2
10 mi
·
11 min
·
CT 2
Use the straight / slight right lanes.
20
Take the exit
0.2 mi
·
36 sec
Exit 15
Toward CT 66: Willimantic, Middletown
Use the slight right lane.
21
Keep slight left at fork
178 ft
·
11 sec
Toward CT 66 East: Hebron, Willimantic
22
Turn left onto CT 66
520 ft
·
6 sec
·
East Hampton Road
23
Continue on CT 66
2.2 mi
·
2 min
·
Hebron Road
24
Continue on CT 66
3.0 mi
·
3 min
·
West Main Street
25
Continue on CT 66
1.4 mi
·
1 min
·
Main Street
26
Continue on CT 66
6.8 mi
·
7 min
·
Middletown Road
Use the straight / right lanes.
27
Take the exit
0.2 mi
·
41 sec
Exit 89
Toward CT 32: Stafford Springs, Willimantic
28
Turn right onto CT 32
0.7 mi
·
1 min
·
Main Street
29
Turn left onto West Avenue
453 ft
·
12 sec
·
West Avenue
30
Turn right onto Valley Street
1.3 mi
·
3 min
·
Valley Street
31
Turn right onto Jackson Street
0.1 mi
·
16 sec
·
Jackson Street
32
Continue on South Street
0.1 mi
·
17 sec
·
South Street
33
Turn left onto CT 32
0.3 mi
·
37 sec
·
Pleasant Street
34
Continue on CT 32
2.8 mi
·
5 min
·
Windham Road
35
Turn right onto Main Street
311 ft
·
15 sec
·
Main Street
36
Turn right
50 ft
·
5 sec
37
Turn left
94 ft
·
6 sec
38
Arrive at destination
Trip Plan
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 52.3 miles from Stamford, CT, or about 1h 9m 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 23 miles or 32m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 52.3 miles or 1h 9m 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 51m
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 Stamford, CT so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Stamford, CT
This is one driving day of about 104.6 miles and 2h 18m.
Your first comfortable stop window is around 23 miles from Stamford, 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.
Mid-route town
Meal stop
52 mi into the route
Best for: Lunch, fuel, and a longer reset
This sits close to the middle of the route, so it works well for the longest stop of the day.
Pacing Suggestions
Fuel and coffee
A short stop after about 23 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 52.3 miles from Stamford, CT, which is a good place for a longer meal and fuel stop.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Heads-up: tricky spots
5 of 285 decision points cluster between mile 21.4 and 71.9 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
8
21.4 mi into trip
|
~30m in
Take the exit toward CT 25, CT 8: Trumbull, Waterbury
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the right lane.
Exit 27A
Toward CT 25, CT 8: Trumbull, Waterbury
8
27 mi into trip
|
~37m 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
57.7 mi into trip
|
~1h 16m 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
71.7 mi into trip
|
~1h 32m 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
71.9 mi into trip
|
~1h 33m 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
Fuel & Cost
Regular Gas
$16.84 one way
$33.68 round trip
$4.09/gal
25.4 MPG avg
37 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.50 | $18.53 | $37.05 |
| premium | $4.86 | $20.03 | $40.06 |
| diesel | $5.61 | $23.09 | $46.19 |
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$17
Meals
$25–$50
Total
$42–$67
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 36.6 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $11 in charging · 0 stops · 68% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 31.4 | 0 | $10.98 | $5.02 |
| Efficient EV | 26.2 | 0 | $9.15 | $4.18 |
| EV Truck/SUV | 41.8 | 0 | $14.64 | $6.69 |
Gas CO2
37 kg
EV CO2
12 kg (68% 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.
Destination
South Windham, CT
Afternoon in South Windham on Saturday
Local time
3:01 PM
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
2h 18m 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...
11 mi from route
~26 min detour
Free
near mile 10.8
View on nps.gov
Park data from the National Park Service API. Alerts update every 2 hours.
What kind of drive is this?
104.6 mi in 2h 18m, mostly highway — 27 mi of that is on Wilbur Cross Parkway.
78% highway — fuel and pacing are the main things to plan.
38 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 95. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 21.4 miles in.
Driving Effort
10/10
High effort - long or complex enough to need steady focus all day
Balances navigation complexity with total wheel time.
This is a demanding drive. With 28 significant decision points across 104.6 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 21.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 27 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 57.7 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.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Stamford, CT and South Windham, CT, road signs point toward Waterbury, New Haven, Middletown, Old Wethersfield and Willimantic.
Waterbury
21.4 mi in
|
~30m
New Haven
25.2 mi in
|
~34m
|
via CT 8
Middletown
57.7 mi in
|
~1h 16m
Old Wethersfield
71.7 mi in
|
~1h 32m
Willimantic
85.2 mi in
|
~1h 50m
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 2h 18m. Total distance: 104.6 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
2h 18m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (78%). 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.
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.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 21.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 27 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 57.7 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.
How this page is built
Compiled by the Trip.ovh planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, EIA for fuel prices, and NPS for national parks. See our methodology for refresh cadence and limitations.
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