Origin
Milford, CT
Morning in Milford on Tuesday
Local time
7:30 AM
EDT
Current temp
43°F
Unavailable
Live forecast
Trip from Milford, CT to Winsted, CT
Pin this tripCompiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Apr 21, 2026 · Editorial standards
Drive Time
1h 14m
Distance
55.2 mi
89 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$9
one way
EV Charging
Fair
3 stations
Best Time to Leave
4 AM
1h 9m
★
6 AM
1h 15m
8 AM
1h 26m
10 AM
1h 19m
12 PM
1h 18m
3 PM
1h 19m
5 PM
1h 26m
8 PM
1h 11m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Milford, CT
Wikimedia Commons
Winsted, CT
Wikimedia Commons
Trip Overview
If you are looking to travel from Milford to Winsted, you are in for a 55.2-mile journey across Connecticut. Expect the drive to take approximately 1 hour and 14 minutes, making it an ideal candidate for a single-day trip. Since the entire route is comprised of local roads rather than interstates, you won’t need to worry about planning for overnight stays. Budget around $9 for fuel to complete the trip comfortably. Navigating through the Northeast, this route offers a straightforward connection between the two towns without the complexity of major highway systems.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| CT 8 | 45.4 mi | 56m |
| Grassy Hill Road | 3.7 mi | 6m |
| North Street | 2.3 mi | 4m |
| New Haven Avenue | 1.6 mi | 2m |
| Derby Turnpike | 0.5 mi | <1m |
| South Main Street | 0.3 mi | <1m |
| Park Place | 0.3 mi | <1m |
| Derby Avenue | 0.3 mi | <1m |
Longest stretch:
CT 8
— 45.4 mi, about 56m
Turn-by-Turn Driving Directions
Step-by-step road directions between Milford, CT and Winsted, CT.
1
Start on Factory Lane
53 ft
·
7 sec
·
Factory Lane
2
Turn right onto CT 162
137 ft
·
2 sec
·
New Haven Avenue
3
Keep slight left at fork onto Daniel Street
475 ft
·
10 sec
·
Daniel Street
4
Turn right onto River Street
0.2 mi
·
29 sec
·
River Street
5
Turn left onto West Main Street
57 ft
·
1 sec
·
West Main Street
6
Keep slight right at fork onto Plymouth Place
387 ft
·
7 sec
·
Plymouth Place
7
Turn slight right onto North Street
0.3 mi
·
30 sec
·
North Street
8
Keep slight left at fork onto North Street
2.0 mi
·
3 min
·
North Street
9
Continue on CT 121
3.7 mi
·
6 min
·
Grassy Hill Road
10
Turn left onto CT 34
0.5 mi
·
40 sec
·
Derby Turnpike
11
Continue on CT 34
1.6 mi
·
2 min
·
New Haven Avenue
12
Continue on CT 34
0.3 mi
·
33 sec
·
Derby Avenue
Use the straight lane.
13
Turn left onto CT 34
508 ft
·
8 sec
·
Main Street
Use the left lane.
14
Take the exit
0.3 mi
·
42 sec
Toward CT 8 North: Waterbury
Use the slight right lane.
15
Merge onto CT 8
17 mi
·
20 min
·
CT 8
Use the straight / slight right lanes.
16
Continue on CT 8
0.4 mi
·
1 min
·
CT 8
Exit 31
Toward I 84 East: Hartford
Use the straight / slight right lanes.
17
Continue on CT 8
28 mi
·
34 min
·
CT 8
Exit 33
Toward I 84 West: Danbury
Use the straight / slight left lanes.
18
At end of road, turn right onto US 44; CT 8; CT 183
0.3 mi
·
52 sec
·
South Main Street
19
Turn right onto CT 8
0.2 mi
·
24 sec
·
Park Place
20
Continue on CT 8
0.1 mi
·
27 sec
·
Park Place
21
Arrive at destination
CT 8
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Mid-route town
Meal stop
28 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 12 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 27.6 miles from Milford, 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 135 decision points cluster between mile 0 and 8.9 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
0 mi into trip
|
~0m in
|
CT 162 / New Haven Avenue
Turn right onto CT 162 / New Haven Avenue
Navigation decision point
5
0 mi into trip
|
~0m in
|
Daniel Street
Keep slight left at fork onto Daniel Street
Highway fork - watch signs carefully
5
0.4 mi into trip
|
~0m in
|
Plymouth Place
Keep slight right at fork onto Plymouth Place
Highway fork - watch signs carefully
6
8.8 mi into trip
|
~15m in
|
CT 34 / Main Street
Turn left onto CT 34 / Main Street
Lane positioning matters here
Use the left lane.
6
8.9 mi into trip
|
~15m in
Take the exit toward CT 8 North: Waterbury
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight right lane.
Toward CT 8 North: Waterbury
Fuel & Cost
Regular Gas
$8.89 one way
$17.77 round trip
$4.09/gal
25.4 MPG avg
19 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.50 | $9.78 | $19.55 |
| premium | $4.86 | $10.57 | $21.14 |
| diesel | $5.61 | $12.19 | $24.37 |
No toll roads detected on this route.
Drive Cost (one way)
Fuel
$9
Estimated CO2 emission: 19.3 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $6 in charging · 0 stops · 68% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 16.6 | 0 | $5.80 | $2.65 |
| Efficient EV | 13.8 | 0 | $4.83 | $2.21 |
| EV Truck/SUV | 22.1 | 0 | $7.73 | $3.53 |
Gas CO2
19 kg
EV CO2
6 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
Winsted, CT
Morning in Winsted on Tuesday
Local time
7:30 AM
EDT
Current temp
60°F
Unavailable
Live forecast
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
17 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 14m 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.
What kind of drive is this?
Prepare for a turn-heavy local drive that stays off the highways entirely. Because your highway share is 0%, your focus will remain on navigating local streets like New Haven Avenue, Daniel Street, and River Street. This is not a high-speed interstate cruise; instead, it is a technical drive that requires your full attention as you transition between local road segments. Since there are no long, uninterrupted stretches, the road keeps you engaged with its consistent, winding character from start to finish.
83% highway — fuel and pacing are the main things to plan.
21 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 45.4 mi on CT 8.
How Hard Is This Drive?
9/10
This is a straightforward highway drive that stays mostly on CT 8 and Grassy Hill Road. 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 162 / New Haven Avenue.
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 55.2 miles you will encounter 13 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 162 / New Haven Avenue): Navigation decision point; near the start (Daniel Street): Highway fork - watch signs carefully; at 0.4 miles (Plymouth Place): Highway fork - watch signs carefully.
About the Cities
Starting in Milford, CT
Full guide →Milford is a city in New Haven County, Connecticut. It is bordered to the south by Long Island sound, to the west by the Housatonic river, to the North by the town of Orange, and to the east by the town of West Haven. Milford is approximately 70 miles east of New York City. Milford is home of the Subway chain of restaurants and the Bic company.
City content from Wikivoyage (CC BY-SA 4.0) and Wikidata (CC0).
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 1h 14m. Total distance: 55.2 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 14m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (83%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 45.4 miles on CT 8. 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 Winsted, 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: near the start (CT 162 / New Haven Avenue): Navigation decision point; near the start (Daniel Street): Highway fork - watch signs carefully; at 0.4 miles (Plymouth Place): Highway fork - watch signs carefully.
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 Winsted, CT before heading back.
How this page is built
Compiled by the US Trip Planner 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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