Origin
Simsbury, CT
Afternoon in Simsbury on Thursday
Local time
4:47 PM
EDT
Current temp
53°F
Unavailable
Live forecast
Trip from Simsbury, CT to Milford, CT
Last recalculated Apr 16, 2026
Drive Time
1h 17m
Distance
52.1 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 12m
★
6 AM
1h 18m
8 AM
1h 30m
10 AM
1h 22m
12 PM
1h 21m
3 PM
1h 22m
5 PM
1h 29m
8 PM
1h 14m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Simsbury, CT
Wikimedia Commons
Milford, CT
Wikimedia Commons
Trip Overview
The drive from Simsbury, CT to Milford, CT covers 52.1 miles and takes about 1h 17m 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, Main Street, Waterville Road for much of the mileage, and the overall profile is turn-heavy local drive. The longest uninterrupted segment is about 10 miles on Wilbur Cross Parkway. At current regular gas prices, budget about $8.39 one way before food or hotel costs.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 1h 17m. Total distance: 52.1 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 17m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (19%). Some complex stretches to watch for.
Scenic Drive
Turn-heavy local drive route profile.
Drive Character
Expect a 1h 17m drive with frequent turns across 52.1 miles of local and secondary roads.
This route has more turning and local-road decision points than a simple highway run.
There are about 23 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 10 miles.
How Hard Is This Drive?
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. You will hit about 8 points where you need to pay attention to lane position or signs. The trickiest moment comes around 5.8 miles in near CT 10 / Waterville Road.
Driving Effort
5/10
Moderate - straightforward overall, but long enough or busy enough to require pacing
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 52.1 miles you will encounter 8 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: at 5.8 miles (CT 10 / Waterville Road): Navigation decision point; at 37 miles (CT 15 / Wilbur Cross Parkway): Merge point - match speed before joining. Lane positioning matters here; at 47 miles: Exit ramp - move to the correct lane early. Lane positioning matters here.
Critical Maneuvers
5 of 8 key pointsThese are the spots where you need to pay the most attention. Preview them before you drive.
4
5.8 mi into trip
|
~12m in
|
CT 10 / Waterville Road
Turn right onto CT 10 / Waterville Road
Navigation decision point
5
37 mi into trip
|
~55m in
|
CT 15 / Wilbur Cross Parkway
Merge onto CT 15 / Wilbur Cross Parkway
Merge point - match speed before joining. Lane positioning matters here
Use the straight / right lanes.
7
47 mi into trip
|
~1h 8m in
Take the exit toward CT 121: Orange
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the straight / right lanes.
Exit 41
Toward CT 121: Orange
4
47.1 mi into trip
|
~1h 8m in
Turn right
Navigation decision point
5
47.2 mi into trip
|
~1h 8m in
|
CT 121 / Grassy Hill Road
At end of road, turn right onto CT 121 / Grassy Hill Road
Navigation decision point
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Wilbur Cross Parkway | 10 mi | 12m |
| Main Street | 5.8 mi | 7m |
| Waterville Road | 5.6 mi | 10m |
| Whitney Avenue | 5.4 mi | 7m |
| Highland Avenue | 4.4 mi | 5m |
| Hopmeadow Street | 4.2 mi | 9m |
| Queen Street | 2.4 mi | 3m |
| North Street | 2.4 mi | 4m |
Longest stretch:
Wilbur Cross Parkway
— 10 mi, about 12m
Turn-by-Turn Driving Directions
Step-by-step road directions between Simsbury, CT and Milford, CT.
1
Start on US 202; CT 10
4.2 mi
·
9 min
·
Hopmeadow Street
2
Continue on US 202; CT 10
0.8 mi
·
1 min
·
Simsbury Road
3
Turn left onto US 44; CT 10
0.7 mi
·
1 min
·
West Main Street
4
Turn right onto CT 10
5.6 mi
·
10 min
·
Waterville Road
5
Continue on CT 10
2.7 mi
·
3 min
·
Main Street
6
Continue on CT 10
1.4 mi
·
1 min
·
Farmington Avenue
7
Continue on CT 10
1.7 mi
·
2 min
·
East Street
Use the straight lane.
8
Continue on CT 10
2.4 mi
·
3 min
·
Queen Street
Use the straight / right lanes.
9
Continue on CT 10
2.4 mi
·
3 min
·
North Main Street
Use the straight / right lanes.
10
Continue on CT 10
1.2 mi
·
1 min
·
South Main Street
Use the straight / right lanes.
11
Continue on CT 10
0.4 mi
·
27 sec
·
Norton Street
12
Turn straight onto CT 10
0.2 mi
·
15 sec
·
Cheshire Road
13
Continue on CT 10
4.4 mi
·
5 min
·
Highland Avenue
Use the straight / right lanes.
14
Continue on CT 10; CT 68; CT 70
3.1 mi
·
3 min
·
Main Street
Use the straight / right lanes.
15
Continue on CT 10
5.4 mi
·
7 min
·
Whitney Avenue
Use the straight / right lanes.
16
Take the ramp
0.2 mi
·
26 sec
17
Merge onto CT 15
10 mi
·
12 min
·
Wilbur Cross Parkway
Use the straight / right lanes.
18
Take the exit
258 ft
·
10 sec
Exit 41
Toward CT 121: Orange
Use the straight / right lanes.
19
Turn right
0.2 mi
·
22 sec
20
At end of road, turn right onto CT 121
2.2 mi
·
3 min
·
Grassy Hill Road
21
Continue on CT 121
2.4 mi
·
4 min
·
North Street
22
At end of road, turn right onto River Street
0.3 mi
·
29 sec
·
River Street
23
Arrive at destination
Factory Lane
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 26 mi from Simsbury, CT · 41m 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 Simsbury, CT, which is a good place for a longer meal and fuel stop.
Arriving in Milford, CT
The final approach into Milford, 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
$8.39 one way
$16.77 round trip
$4.09/gal
25.4 MPG avg
18 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.50 | $9.23 | $18.46 |
| premium | $4.86 | $9.98 | $19.95 |
| diesel | $5.61 | $11.50 | $23.01 |
No toll roads detected on this route.
Drive Cost (one way)
Fuel
$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 | $5.47 | $2.50 |
| Efficient EV | 13 | 0 | $4.56 | $2.08 |
| EV Truck/SUV | 20.8 | 0 | $7.29 | $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
Milford, CT
Afternoon in Milford on Thursday
Local time
4:47 PM
EDT
Current temp
43°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
10 degrees cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
1h 17m 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 Simsbury, CT to Milford, CT covers 52.1 miles and takes about 1h 17m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Wilbur Cross Parkway, Main Street, Waterville Road. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 26 miles from Simsbury, CT. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $8.39 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 52.1 miles you will encounter 8 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: at 5.8 miles (CT 10 / Waterville Road): Navigation decision point; at 37 miles (CT 15 / Wilbur Cross Parkway): Merge point - match speed before joining. Lane positioning matters here; at 47 miles: Exit ramp - move to the correct lane early. Lane positioning matters here.
The route from Simsbury, CT to Milford, CT does not surface many named destination signs beyond the main corridor.
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