How far is Cheshire, CT from Milford, CT?
The driving distance from Cheshire, CT to Milford, CT is about 26 miles (41.8 km), with a travel time of about 00h 40m by car.
- The straight-line flight distance is about 20.8 miles (33.4 km).
- For a round trip, plan for roughly 01h 20m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 7:00 AM to 7:00 PM EDT.
Reverse, save, or send this route
This is an easy same-day return drive. Copy the route link, send it to another device, or print a clean version before you head out.
This is an easy same-day return drive.
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 00h 40m.
This is a short drive, so your comfort window is wide. Traffic and current weather matter more than the clock.
This departure sits inside the recommended comfort window for the route.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Town in Connecticut
Route Weather Snapshot
Check the forecast at both ends before you head out.
Showers And Thunderstorms
Showers And Thunderstorms
Driving Route Map
The map below follows the saved road route between Cheshire and Milford.
Turn-by-Turn Driving Directions
Step-by-step road directions between Cheshire and Milford.
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1
Start on the route
157 m · 40 sec
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2
Turn right onto Woodbury Court
93 m · 15 sec · Woodbury Court
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3
Turn right onto Academy Road
610 ft · 18 sec · Academy Road
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4
At the end of the road, turn left onto South Main Street
3 mi · 4 min · South Main Street
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5
Continue on Whitney Avenue
5.4 mi · 7 min · Whitney Avenue
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6
Take the ramp slight right
1084 ft · 26 sec
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7
Merge slight left onto Wilbur Cross Parkway
10 mi · 13 min · Wilbur Cross Parkway
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8
Take the exit slight right toward CT 121: Orange
79 m · 10 sec
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9
Turn right
856 ft · 23 sec
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10
At the end of the road, turn right onto Grassy Hill Road
2.2 mi · 4 min · Grassy Hill Road
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11
Continue on North Street
2.4 mi · 5 min · North Street
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12
At the end of the road, turn right onto River Street
1324 ft · 30 sec · River Street
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13
Arrive at your destination
0 m · 1 sec · Factory Lane
Car Route Details
A richer read on the saved driving route between Cheshire and Milford.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
Wilbur Cross Parkway
Merge slight left onto Wilbur Cross Parkway
10 mi · 00h 13m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A short regional drive
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
Showers And Thunderstorms leaving Cheshire and Showers And Thunderstorms near Milford.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Cheshire to Milford?
The road trip is about 26 miles (41.8 km) and usually takes 00h 40m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
What is the halfway point on this route?
Woodbridge is a useful midpoint, sitting about 12 miles from Cheshire and 14 miles from Milford.
How much longer is the road route than the straight-line distance?
The direct path is about 20.8 miles (33.4 km), while the road route adds roughly 5.2 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 7:00 AM to 7:00 PM EDT. If you want a more comfortable same-day return, try to leave by 7:10 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $3.63 one way or $7.26 round trip. Estimated CO2 is about 8.2 kg one way.
What should you check before leaving?
Before you leave, expect Showers And Thunderstorms around Cheshire and Showers And Thunderstorms near Milford.
Stop Ideas Near Woodbridge
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 Woodbridge.
Union Station
Wallingford station
Bridgeport
Meriden Transit Center
Flight Path Map
This map shows the direct air route between Cheshire and Milford. Straight-line distance: 20.75 mi (33.4 km).
#1 Cheshire
Town in Connecticut
| Population | 28,806 |
| Coordinates | 41.4989900, -72.9006600 |
| Altitude | 78 |
| 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: 42 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 00h 51m |
| 40 mph (64.37 km/h) | 00h 38m |
| 50 mph (80.47 km/h) | 00h 31m |
| 60 mph (96.56 km/h) | 00h 25m |
| 70 mph (112.65 km/h) | 00h 22m |
| 80 mph (129 km/h) | 00h 19m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $3.63 | $7.26 |
| Mid-grade | $4.46 | $4.10 | $8.20 |
| Premium | $4.86 | $4.47 | $8.94 |
| Diesel | $6.00 | $5.52 | $11.03 |
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 · May 25, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.