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Trip from North 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 15m

Distance

102.9 mi

166 km

Drive Score

9/10

Great drive

Same Day?

Yes, doable

Fuel Cost

$17

one way

EV Charging

Unknown

Best Time to Leave

Save up to 29 min
4 AM
2h 6m ★
6 AM
2h 16m
8 AM
2h 35m
10 AM
2h 22m
12 PM
2h 20m
3 PM
2h 23m
5 PM
2h 34m
8 PM
2h 10m

Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.

Best Time Drive vs Fly
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city in Fairfield County, Connecticut, United States

North Stamford, CT

David Kanigan

Trip Overview

The drive from North Stamford, CT to South Windham, CT covers 102.9 miles and takes about 2h 15m 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, Merritt Parkway, I 91 for much of the mileage, and the overall profile is highway-focused drive. The longest uninterrupted segment is about 27 miles on Wilbur Cross Parkway. At current regular gas prices, budget about $16.57 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

51.4 miles from North Stamford, CT

A natural place for your longest stop of the day , about 1h 8m into the drive .

Main Roads

Road Distance Duration
Wilbur Cross Parkway 27 mi 33m
Merritt Parkway 26.7 mi 35m
I 91 13.6 mi 15m
CT 2 10.6 mi 12m
Middletown Road 6.8 mi 7m
West Main Street 3 mi 3m
Windham Road 2.8 mi 5m
Hebron Road 2.2 mi 2m
Longest stretch: Wilbur Cross Parkway — 27 mi, about 33m

Turn-by-Turn Driving Directions

Step-by-step road directions between North Stamford, CT and South Windham, CT.

1

Start on Cascade Road

139 ft · 6 sec · Cascade Road
2

Turn straight onto North Stamford Road

475 ft · 18 sec · North Stamford Road
3

Continue on North Stamford Road

0.2 mi · 50 sec · North Stamford Road
4

Turn left onto CT 137

1.7 mi · 3 min · High Ridge Road
5

Take the ramp

0.3 mi · 41 sec
6

Merge onto CT 15

27 mi · 35 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 65A Toward I 91 North, CT 66 East: Hartford, Middletown Use 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 25-26 Toward CT 3 North: Glastonbury, Old Wethersfield Use the slight right lane.
11

Keep slight left at fork

0.3 mi · 36 sec
Exit 25 Toward CT 3 North: Glastonbury Use 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 C Toward CT 2 East: Norwich Use 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 15 Toward CT 66: Willimantic, Middletown Use 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 89 Toward 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

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 51.4 miles from North Stamford, CT, or about 1h 8m 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 51.4 miles or 1h 8m 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 48m

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 North 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 North Stamford, CT

This is one driving day of about 102.9 miles and 2h 15m.

Your first comfortable stop window is around 23 miles from North 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.

town in Hartford County, Connecticut, USA

Mid-route town

Meal stop

Glastonbury, CT

51 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

New Haven, CT

Fuel and coffee

A short stop after about 23 miles helps settle the day before fatigue starts building.

Meriden, CT

Meal break

The midpoint is around 51.4 miles from North 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.

Nearby Places

Restaurants, cafes, gas stations and more along your route.

Top Restaurant

Bob's Coffee Shop

4.6 ★ ★ ★ ★ ★

Rocky Hill, Connecticut

Around the midpoint, right off the route

0.7 mi from route ~2 min detour $10 to $20 mile 66.1

Hours: 6:30 am–2 pm

+18605292540

Visit website

Glastonbury Coffee Shop

4.4 ★ ★ ★ ★ ☆

Glastonbury, Connecticut

0.5 mi

Christo's Restaurant & Bar

4.5 ★ ★ ★ ★ ★

Wallingford, Connecticut

0.8 mi

Bob's Coffee Shop

4.6 ★ ★ ★ ★ ★

Around the midpoint, right off the route

0.7 mi from route ~2 min detour $10 to $20 mile 66.1

Rocky Hill, Connecticut

Hours: 6:30 am–2 pm

+18605292540

Visit website

Glastonbury Coffee Shop

4.4 ★ ★ ★ ★ ☆

Later in the drive, right off the route

0.5 mi from route ~1 min detour $10 to $20 mile 73.5

Glastonbury, Connecticut

Hours: 6 am–1 pm

+18606590182

Visit website

Christo's Restaurant & Bar

4.5 ★ ★ ★ ★ ★

Around the midpoint, right off the route

0.8 mi from route ~2 min detour $20 to $30 mile 51.4

Wallingford, Connecticut

Hours: 11 am–11 pm

+12032944626

Visit website

99 Restaurants

4.3 ★ ★ ★ ★ ☆

Around the midpoint, right off the route

0.7 mi from route ~2 min detour Moderately mile 51.4

Wallingford, Connecticut

Hours: 11:30 am–10:30 pm

+12032849989

Visit website

The Flour Girl Cafe

4.6 ★ ★ ★ ★ ★

Near the end, right off the route

0.8 mi from route ~2 min detour $10 to $20 mile 88.2

Hebron, Connecticut

Hours: 6:30 am–4 pm

+18605301536

Visit website

Thunderbird Cafe

4.6 ★ ★ ★ ★ ★

Near the end, right off the route

0.5 mi from route ~1 min detour $1 to $10 mile 95.5

Columbia, Connecticut

Hours: 7:30 am–2 pm

+18602282886

Visit website

Old Towne Restaurant

4.3 ★ ★ ★ ★ ☆

Early in the drive, short detour

1.6 mi from route ~4 min detour $20 to $30 mile 22

Trumbull, Connecticut

Hours: 9 am–9 pm

+12032619436

Visit website

Giulia's Pizza Restaurant

4.8 ★ ★ ★ ★ ★

Around the midpoint, short detour

1.9 mi from route ~5 min detour $10 to $20 mile 66.1

Cromwell, Connecticut

Hours: 12–8 pm

+18607882200

Visit website

The Taste Garden Cafe and Catering

4.9 ★ ★ ★ ★ ★

Early in the drive, ~9 min detour

3.6 mi from route ~9 min detour $10 to $20 mile 29.4

Trumbull, Connecticut

Hours: 7:30 am–3 pm

+12035028355

Visit website

TheSpot Cafe'

4.8 ★ ★ ★ ★ ★

Later in the drive, ~11 min detour

4.5 mi from route ~11 min detour $10 to $20 mile 73.5

East Hartford, Connecticut

Hours: 6 am–2 pm

+18603102283

Kickstart Cafe

4.8 ★ ★ ★ ★ ★

Early in the drive, ~12 min detour

4.8 mi from route ~12 min detour $1 to $10 mile 29.4

Shelton, Connecticut

Hours: 6 am–3 pm

+12035132106

Visit website

Sacred Heart University Discovery Science Center and Planetarium

4.0 ★ ★ ★ ★ ☆

Early in the drive, short detour

1.4 mi from route ~4 min detour mile 22

Bridgeport, Connecticut

Hours: 10 am–5 pm

+12034163521

Visit website

Milford Green

4.6 ★ ★ ★ ★ ★

Early in the drive, short detour

2.2 mi from route ~5 min detour mile 29.4

Milford, Connecticut

Hours: Open 24 hours

Visit website

Connecticut's Beardsley Zoo

4.4 ★ ★ ★ ★ ☆

Early in the drive, short detour

2.5 mi from route ~6 min detour mile 22

Bridgeport, Connecticut

Hours: 9 am–4 pm

+12033946565

Visit website

Stepping Stones Museum for Children

4.3 ★ ★ ★ ★ ☆

Near the start, short detour

2.7 mi from route ~7 min detour mile 7.3

Norwalk, Connecticut

Hours: 10 am–5 pm

+12038990606

Visit website

Yale University Art Gallery

4.8 ★ ★ ★ ★ ★

Around the midpoint, ~9 min detour

3.5 mi from route ~9 min detour mile 36.7

New Haven, Connecticut

Hours: 10 am–8 pm

+12034320600

Visit website

The Mead Visitor Center

4.6 ★ ★ ★ ★ ★

Around the midpoint, ~9 min detour

3.7 mi from route ~9 min detour mile 36.7

New Haven, Connecticut

Hours: 9 am–4 pm

+12034322300

Visit website

Blessed Michael McGivney Pilgrimage Center (formerly Knights of Columbus Museum)

4.7 ★ ★ ★ ★ ★

Around the midpoint, ~10 min detour

3.9 mi from route ~10 min detour mile 36.7

New Haven, Connecticut

Hours: 10 am–4 pm

+12038650400

Visit website

Salmon River State Forest

4.7 ★ ★ ★ ★ ★

Later in the drive, ~12 min detour

4.7 mi from route ~12 min detour mile 80.8

Colchester, Connecticut

Hours: 8 am–5 pm

+18604243000

Visit website

Place data sourced from public business listings. Hours and availability may vary.

Heads-up: tricky spots

5 of 24

5 decision points cluster between mile 56 and 83.2 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.

8
56 mi into trip | ~1h 13m 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
69.9 mi into trip | ~1h 30m 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
70.1 mi into trip | ~1h 30m 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
72.3 mi into trip | ~1h 34m 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
8
83.2 mi into trip | ~1h 47m in

Take the exit toward CT 66: Willimantic, 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 15 Toward CT 66: Willimantic, Middletown

Fuel & Cost

Regular Gas

$16.57 one way

$33.13 round trip

$4.09/gal 25.4 MPG avg 36 kg CO2
Fuel Type $/gal One Way Round Trip
midgrade $4.50 $18.23 $36.45
premium $4.86 $19.70 $39.41
diesel $5.61 $22.72 $45.44

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 kg one way. Prices: EIA weekly data, 2026-04-13.

Driving Electric?

About $11 in charging · 0 stops · 67% less CO2

Vehicle Type kWh Stops DC Fast Home Charge
Average EV 30.9 0 $10.80 $4.94
Efficient EV 25.7 0 $9.00 $4.12
EV Truck/SUV 41.2 0 $14.41 $6.59

Gas CO2

36 kg

EV CO2

12 kg (67% 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 15, 2026

Origin

North Stamford, CT

Afternoon in North Stamford on Saturday

Local time

3:24 PM

EDT

Current temp

44°F

Unavailable

Live forecast

Destination

South Windham, CT

Afternoon in South Windham on Saturday

Local time

3:24 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 15m 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

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...

8 mi from route ~19 min detour Free near mile 10.6
View on nps.gov

Park data from the National Park Service API. Alerts update every 2 hours.

What kind of drive is this?

This is a 2h 15m highway drive covering 102.9 miles, with most of the trip on Wilbur Cross Parkway and Merritt Parkway. The longest continuous stretch is about 27 miles on Wilbur Cross Parkway.

Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 34 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Wilbur Cross Parkway is the longest continuous segment at about 27 miles.

How Hard Is This Drive?

10/10

This is a straightforward highway drive that stays mostly on Wilbur Cross Parkway and Merritt Parkway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 56 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 24 significant decision points across 102.9 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 56 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 69.9 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 70.1 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.

Between North Stamford, CT and South Windham, CT, road signs point toward Middletown, Old Wethersfield and Willimantic.

Middletown

56 mi in | ~1h 13m

Old Wethersfield

69.9 mi in | ~1h 30m

Willimantic

83.5 mi in | ~1h 47m

Who Is This Route For?

Weekend Trip

Doable as a same-day drive at 2h 15m. Total distance: 102.9 miles.

Family Friendly

Moderate complexity with 0 natural rest stops along the way.

Solo Traveler

2h 15m drive, comfortable solo distance.

First-Time Driver

Mostly highway driving (78%). Some complex stretches to watch for.

Frequently Asked Questions

The drive from North Stamford, CT to South Windham, CT covers 102.9 miles and takes about 2h 15m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.

The main roads are Wilbur Cross Parkway, Merritt Parkway, I 91. Most of the drive stays on highways, so watch for ramps and exits.

This is a comfortable same-day trip.

The midpoint is about 51.4 miles from North Stamford, CT. Look for rest areas, gas stations, or food options near the halfway mark.

At current regular gas prices, expect to spend about $16.57 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.

Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.

This is a demanding drive. With 24 significant decision points across 102.9 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.

The main spots that need attention: at 56 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 69.9 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 70.1 miles: Highway fork - watch signs carefully. Lane positioning matters here.

Between North Stamford, CT and South Windham, CT, road signs point toward Middletown, Old Wethersfield and Willimantic.

Yes. Nearby national parks include Weir Farm National Historical Park.

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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