How far is Winsted, CT from Milford, CT?
The driving distance from Winsted, CT to Milford, CT is about 54.1 miles (87 km), with a travel time of about 01h 00m by car.
- The straight-line flight distance is about 48.3 miles (77.7 km).
- For a round trip, plan for roughly 02h 01m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 01h 00m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
This departure sits inside the recommended comfort window for the route.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
The second most populous city in Connecticut.
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Winsted and Milford.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winsted and Milford.
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1
Start on Park Place
31 m · 12 sec · Park Place
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2
Turn left onto South Main Street
2366 ft · 1 min · South Main Street
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3
Continue on CT 8 SOUTH: Torrington, Waterbury
45.6 mi · 55 min
-
4
Take the exit slight right toward CT 34: Derby, New Haven
708 ft · 33 sec
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5
Turn right onto Main Street
936 ft · 16 sec · Main Street
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6
Turn right onto Derby Avenue
1356 ft · 34 sec · Derby Avenue
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7
Continue on New Haven Avenue
1.6 mi · 2 min · New Haven Avenue
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8
Continue on Derby Turnpike
2613 ft · 38 sec · Derby Turnpike
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9
Turn right onto Grassy Hill Road
3.7 mi · 7 min · Grassy Hill Road
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10
Continue on North Street
2.4 mi · 5 min · North Street
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11
At the end of the road, turn right onto River Street
1324 ft · 30 sec · River Street
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12
Arrive at your destination
0 m · 1 sec · Factory Lane
Car Route Details
A richer read on the saved driving route between Winsted and Milford.
Straightforward drive
The saved road route has a manageable number of maneuvers and should be easy to follow with normal attention to signs.
CT 8 SOUTH
Continue on CT 8 SOUTH: Torrington, Waterbury
45.6 mi · 00h 55m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Mostly Sunny near Winsted.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winsted to Milford?
The road trip is about 54.1 miles (87 km) and usually takes 01h 00m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Waterbury is a useful midpoint, sitting about 27.6 miles from Winsted and 26.5 miles from Milford.
How much longer is the road route than the straight-line distance?
The direct path is about 48.3 miles (77.7 km), while the road route adds roughly 5.8 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 4:28 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $7.53 one way or $15.07 round trip. Estimated CO2 is about 17 kg one way.
What should you check before leaving?
Before leaving, the latest forecast around Winsted is Mostly Sunny.
Stop Ideas Near Waterbury
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Waterbury.
Meriden Transit Center
Wallingford station
Berlin
Union Station
Flight Path Map
This map shows the direct air route between Winsted and Milford. Straight-line distance: 48.29 mi (77.71 km).
#1 Winsted
City in Connecticut, United States
| Population | 7,712 |
| Coordinates | 41.9212100, -73.0601100 |
| Altitude | 216 |
| Country | United States |
#2 Milford
A city in New Haven County, Connecticut.
| Population | 53,259 |
| Coordinates | 41.2223200, -73.0565000 |
| Altitude | 8 |
| Country | United States |
End: Factory Lane (-73.056608, 41.222268)
Estimated Travel Time
Distance: 87 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 48m |
| 40 mph (64.37 km/h) | 01h 21m |
| 50 mph (80.47 km/h) | 01h 04m |
| 60 mph (96.56 km/h) | 00h 54m |
| 70 mph (112.65 km/h) | 00h 46m |
| 80 mph (129 km/h) | 00h 40m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $7.53 | $15.07 |
| Mid-grade | $4.46 | $8.51 | $17.03 |
| Premium | $4.86 | $9.28 | $18.56 |
| Diesel | $6.00 | $11.45 | $22.91 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in Connecticut · Apr 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.