If you are looking to travel from Windham to Stamford, expect a journey covering 107 miles of Connecticut's local landscape. This trip typically takes about 1 hour and 53 minutes to complete, making it a manageable day trip that does not require an overnight stay. You should budget approximately $17 for fuel to cover the distance. Because the route relies entirely on local roads rather than major interstates, you will experience a slower, more deliberate pace. It is a straightforward trek across the Northeast region, ideal for those who prefer avoiding highway congestion.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
53.2 miles from Windham, CT
A natural place for your longest stop of the day
, about 1h 9m into the drive
.
Main Roads
Road
Distance
Duration
CT 15
29.8 mi
37m
I 95
20.6 mi
28m
I 91
13.3 mi
15m
CT 2
11 mi
12m
US 6
5 mi
6m
Middletown Road
5 mi
5m
CT 8
4.5 mi
5m
West Main Street
3 mi
3m
Longest stretch:
CT 15
— 29.8 mi, about 37m
Turn-by-Turn Driving Directions
Step-by-step road directions between Windham, CT and Stamford, CT.
1
Start on CT 14
200 ft·6 sec·Scotland Road
2
Turn right onto CT 14; CT 203
0.8 mi·1 min·North Road
3
Continue on CT 14
0.1 mi·15 sec·Bricktop Road
4
Turn right onto Tuckie Road
1.9 mi·4 min·Tuckie Road
5
At end of road, turn right onto CT 66
290 ft·5 sec·Boston Post Road
6
Take the ramp
0.6 mi·1 min
7
Merge onto US 6
5.0 mi·6 min·US 6
8
Keep slight left at fork onto CT 66
5.0 mi·5 min·Middletown Road
Use the straight / right lanes.
9
Continue on CT 66
1.4 mi·1 min·Main Street
Use the straight / right lanes.
10
Continue on CT 66
3.0 mi·3 min·West Main Street
Use the left / straight / right lanes.
11
Continue on CT 66
2.2 mi·2 min·Hebron Road
12
Take the exit
0.2 mi·24 sec
Toward CT 2 West: Hartford
13
Merge onto CT 2
11 mi·12 min·CT 2
Use the straight / slight right lanes.
14
Take the exit
0.6 mi·1 min
Exit 4Toward CT 3 South: WethersfieldUse the slight right lane.
15
Continue on this road
0.2 mi·29 sec·this road
Exit 5DToward CT 3 South: Wethersfield
16
Continue on CT 3
2.2 mi·3 min·CT 3
Use the straight / slight right lanes.
17
Take the exit
0.7 mi·1 min
Toward I 91 South: New HavenUse the straight / slight left lanes.
18
Merge onto I 91
13 mi·15 min·I 91
Use the straight / slight right lanes.
19
Take the exit
0.3 mi·34 sec
Exit 17Toward CT 15 SouthUse the slight right lane.
20
Keep slight left at fork
437 ft·8 sec
Toward CT 15 SouthUse the straight / slight right lanes.
21
Merge onto CT 15
30 mi·37 min·CT 15
Use the straight / slight right lanes.
22
Take the exit
0.2 mi·23 sec
Exit 34Toward CT 8, CT 108: Bridgeport, WaterburyUse the straight / slight right lanes.
23
Keep slight left at fork
0.4 mi·48 sec
Toward CT 8 South, CT 108 South: Bridgeport
24
Keep slight left at fork
0.8 mi·1 min
Toward CT 8 South: BridgeportUse the slight left lane.
25
Merge onto CT 8
4.5 mi·5 min·CT 8
26
Keep slight right at fork
0.3 mi·42 sec
Toward I 95 South: New York CityUse the slight right lane.
27
Merge onto I 95
21 mi·28 min·I 95
Use the straight / slight right lanes.
28
Take the exit
0.2 mi·31 sec
Exit 7Toward CT 137 North: Atlantic StreetUse the slight right lane.
29
Turn straight onto North State Street
0.3 mi·47 sec·North State Street
30
Turn right onto Atlantic Street
0.3 mi·38 sec·Atlantic Street
31
Arrive at destination
Atlantic Street
Trip Plan
Since this is a sub-two-hour drive, you have significant flexibility in your departure timing to avoid peak local traffic. Given the absence of planned stops in the data, ensure your vehicle is fueled up before you head out, as the $17 estimate assumes a steady run without frequent idling. Keep a close eye on your GPS, as the reliance on secondary roads like Tuckie Road means there are plenty of intersections to navigate. If you find the constant turns fatiguing, plan for a quick pull-off to stretch your legs, as there are no official transit breaks built into this 107-mile path. Staying alert at every turn is your best strategy for a smooth arrival in Stamford.
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 53.2 miles from Windham, CT, or about 1h 9m into the drive.
The longest continuous stretch on this route runs about 29.8 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 31m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 53.2 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 52m
Traffic, exits, and arrival timing usually matter more near Stamford, CT than in the middle of the route.
Before You Leave
+
Open the route before leaving Windham, 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 Windham, CT
This is one driving day of about 106.3 miles and 2h 19m.
Your first comfortable stop window is around 23 miles from Windham, CT.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on CT 15 for about 29.8 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 21
5 decision points cluster between mile 31.4 and 79.3 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
7
31.4 mi into trip|~41m in
Take the exit toward CT 3 South: Wethersfield
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight right lane.
Exit 4
Toward CT 3 South: Wethersfield
7
48.4 mi into trip|~1h 3m in
Take the exit toward CT 15 South
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight right lane.
Exit 17
Toward CT 15 South
7
48.7 mi into trip|~1h 3m in
Keep slight left at fork toward CT 15 South
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Toward CT 15 South
8
78.6 mi into trip|~1h 41m in
Take the exit toward CT 8, CT 108: Bridgeport, Waterbury
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 34
Toward CT 8, CT 108: Bridgeport, Waterbury
7
79.3 mi into trip|~1h 42m in
Keep slight left at fork toward CT 8 South: Bridgeport
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left lane.
Toward CT 8 South: Bridgeport
Fuel & Cost
Regular Gas
$17.11 one way
$34.23 round trip
$4.09/gal25.4 MPG avg37 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.50
$18.83
$37.66
premium
$4.86
$20.36
$40.71
diesel
$5.61
$23.47
$46.94
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: 37.2 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
31.9
0
$11.16
$5.10
Efficient EV
26.6
0
$9.30
$4.25
EV Truck/SUV
42.5
0
$14.88
$6.80
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.
Forecast as of Apr 17, 2026
Origin
Windham, CT
Night
in Windham on Saturday
Local time
9:26 PM
EDT
Current temp
82°F
Unavailable
Live forecast
Destination
Stamford, CT
Night
in Stamford on Saturday
Local time
9:26 PM
EDT
Current temp
76°F
Scattered Showers And Thunderstorms
NE 9 mph54% chanceLive 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
6 degrees cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
2h 19m on the road
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
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 95.3
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Prepare for a turn-heavy local drive that keeps you engaged behind the wheel. Unlike a monotonous interstate grind, this 107-mile route features a 0% highway share, meaning you will navigate through local thoroughfares like North Road, Bricktop Road, and Tuckie Road for the duration of the trip. The character of the drive is defined by its technical nature, requiring constant attention as you transition between these smaller roads. Expect a consistent, winding experience rather than long, uninterrupted stretches of straight pavement. This route is best suited for drivers who enjoy the nuances of local navigation over the high-speed transit of major highways.
81% highway — fuel and pacing are the main things to plan.
31 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 29.8 mi on CT 15.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on CT 15 and I 95. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 31.4 miles in.
Driving Effort10/10
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 21 significant decision points across 106.3 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 31.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here; at 48.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here; at 48.7 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
On the drive from Windham, CT to Stamford, CT, road signs begin pointing toward Waterbury along the way.
Waterbury
78.6 mi in|~1h 41m
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 2h 19m. Total distance: 106.3 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
2h 19m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (81%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 29.8 miles on CT 15. 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 Stamford, 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 31.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here; at 48.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here; at 48.7 miles: Highway fork - watch signs carefully. Lane positioning matters here.
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 Stamford, CT before heading back.
