Origin
Shelton, CT
Afternoon in Shelton on Friday
Local time
2:44 PM
EDT
Current temp
42°F
Unavailable
Live forecast
Trip from Shelton, CT to Windsor, CT
Compiled and reviewed by the Trip.ovh planning team at COD Solutions Oy · Last reviewed Apr 17, 2026 · Editorial standards
Drive Time
1h 8m
Distance
52 mi
84 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$8
one way
EV Charging
Unknown
Best Time to Leave
4 AM
1h 3m
★
6 AM
1h 8m
8 AM
1h 19m
10 AM
1h 12m
12 PM
1h 11m
3 PM
1h 12m
5 PM
1h 18m
8 PM
1h 5m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Shelton, CT
Wikimedia Commons
Windsor, CT
Wikimedia Commons
Trip Overview
The drive from Shelton, CT to Windsor, CT covers 52 miles and takes about 1h 8m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on I 91, Wilbur Cross Parkway, New Haven Avenue for much of the mileage, and the overall profile is highway-focused drive. The longest uninterrupted segment is about 24.4 miles on I 91. At current regular gas prices, budget about $8.37 one way before food or hotel costs.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 1h 8m. Total distance: 52 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 8m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (91%). Some complex stretches to watch for.
Drive Character
This is a 1h 8m highway drive covering 52 miles, with most of the trip on I 91 and Wilbur Cross Parkway. The longest continuous stretch is about 24.4 miles on I 91.
Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 18 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
I 91 is the longest continuous segment at about 24.4 miles.
How Hard Is This Drive?
This is a straightforward highway drive that stays mostly on I 91 and Wilbur Cross Parkway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes early in the drive near CT 108 / Center Street.
Driving Effort
9/10
Demanding - stay alert through the decision-heavy sections
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 52 miles you will encounter 14 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: near the start (CT 108 / Center Street): Navigation decision point; at 25.9 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 44 miles (I 91): Highway fork - watch signs carefully. Lane positioning matters here.
Critical Maneuvers
5 of 14 key pointsThese are the spots where you need to pay the most attention. Preview them before you drive.
5
0 mi into trip
|
~0m in
|
CT 108 / Center Street
Turn right onto CT 108 / Center Street
Navigation decision point
8
25.9 mi into trip
|
~33m 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...
6
44 mi into trip
|
~55m in
|
I 91
Keep slight right at fork onto I 91
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
8
50.7 mi into trip
|
~1h 4m in
Take the exit toward CT 305: Bloomfield Avenue, Windsor Center
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 37
Toward CT 305: Bloomfield Avenue, Windsor Cente...
7
51.9 mi into trip
|
~1h 7m in
|
CT 75 / Poquonock Avenue
At end of road, turn right onto CT 75 / Poquonock Avenue
Lane positioning matters here
Use the left / right lanes.
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 Shelton, CT to Windsor, CT, road signs begin pointing toward Middletown along the way.
Middletown
25.9 mi in
|
~33m
Main Roads
| Road | Distance | Duration |
|---|---|---|
| I 91 | 24.4 mi | 30m |
| Wilbur Cross Parkway | 21.8 mi | 26m |
| New Haven Avenue | 1.6 mi | 2m |
| Derby Turnpike | 1.3 mi | 1m |
| Bloomfield Avenue | 1 mi | 2m |
| Main Street | 0.5 mi | 1m |
| Derby Avenue | 0.3 mi | <1m |
| Bridge Street | 0.2 mi | <1m |
Longest stretch:
I 91
— 24.4 mi, about 30m
Turn-by-Turn Driving Directions
Step-by-step road directions between Shelton, CT and Windsor, CT.
1
Start on this road
62 ft
·
6 sec
·
this road
2
Turn right onto CT 108
181 ft
·
10 sec
·
Center Street
3
Turn left onto CT 110
283 ft
·
8 sec
·
Howe Avenue
4
Turn right onto Bridge Street
0.2 mi
·
29 sec
·
Bridge Street
5
Turn right onto CT 34
0.5 mi
·
1 min
·
Main Street
6
Turn right onto Derby Avenue
0.3 mi
·
33 sec
·
Derby Avenue
Use the left / right lanes.
7
Continue on CT 34
1.6 mi
·
2 min
·
New Haven Avenue
8
Continue on CT 34
1.3 mi
·
1 min
·
Derby Turnpike
9
Take the exit
0.1 mi
·
26 sec
Toward CT 15 North: New Haven
10
Merge onto CT 15
22 mi
·
26 min
·
Wilbur Cross Parkway
Use the straight / right lanes.
11
Take the exit
0.3 mi
·
38 sec
Exit 65A
Toward I 91 North, CT 66 East: Hartford, Middletown
Use the slight right lane.
12
Merge onto I 91
18 mi
·
21 min
·
I 91
Use the straight / slight right lanes.
13
Keep slight right at fork onto I 91
6.7 mi
·
8 min
·
I 91
Use the straight / slight right lanes.
14
Take the exit
0.2 mi
·
32 sec
Exit 37
Toward CT 305: Bloomfield Avenue, Windsor Center
Use the straight / slight right lanes.
15
Turn right onto CT 305
1.0 mi
·
2 min
·
Bloomfield Avenue
Use the right lane.
16
At end of road, turn right onto CT 75
394 ft
·
15 sec
·
Poquonock Avenue
Use the left / right lanes.
17
Continue on Broad Street
56 ft
·
2 sec
·
Broad Street
Use the straight / left lanes.
18
Arrive at destination
Broad Street
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 26 mi from Shelton, CT · 33m into the drive
Mid-route town
Meal stop
26 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 11 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 26 miles from Shelton, CT, which is a good place for a longer meal and fuel stop.
Arriving in Windsor, CT
The final approach into Windsor, CT usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Fuel & Cost
Regular Gas
$8.37 one way
$16.74 round trip
$4.09/gal
25.4 MPG avg
18 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.50 | $9.21 | $18.42 |
| premium | $4.86 | $9.96 | $19.92 |
| diesel | $5.61 | $11.48 | $22.96 |
Estimated Tolls: $0.09
Derby Turnpike
(1.3 mi)
$0.09
Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.
Drive Cost (one way)
Fuel
$8
Tolls
$0
Total
$8
Estimated CO2 emission: 18.2 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $5 in charging · 0 stops · 67% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 15.6 | 0 | $5.46 | $2.50 |
| Efficient EV | 13 | 0 | $4.55 | $2.08 |
| EV Truck/SUV | 20.8 | 0 | $7.28 | $3.33 |
Gas CO2
18 kg
EV CO2
6 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.
Destination
Windsor, CT
Afternoon in Windsor on Friday
Local time
2:44 PM
EDT
Current temp
42°F
Unavailable
Live forecast
42°F
Middletown, CT
26 mi in
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
Very similar conditions
Both ends of the route are sitting at about the same temperature right now.
Road read
1h 8m 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.
Frequently Asked Questions
The drive from Shelton, CT to Windsor, CT covers 52 miles and takes about 1h 8m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are I 91, Wilbur Cross Parkway, New Haven Avenue. Most of the drive stays on highways, so watch for ramps and exits.
This is a comfortable same-day trip.
The midpoint is about 26 miles from Shelton, CT. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $8.37 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 drive requires moderate attention. Across 52 miles you will encounter 14 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
The main spots that need attention: near the start (CT 108 / Center Street): Navigation decision point; at 25.9 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 44 miles (I 91): Highway fork - watch signs carefully. Lane positioning matters here.
On the drive from Shelton, CT to Windsor, CT, road signs begin pointing toward Middletown along the way.
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, and EIA for fuel prices. See our methodology for refresh cadence and limitations.
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