Origin
Monroe, CT
Late night in Monroe on Sunday
Local time
3:54 AM
EDT
Current temp
55°F
Unavailable
Live forecast
Trip from Monroe, CT to Middletown, CT
Compiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Apr 19, 2026 · Editorial standards
Drive Time
57m
Distance
39.5 mi
64 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$6
one way
EV Charging
Unknown
Best Time to Leave
4 AM
0h 53m
★
6 AM
0h 58m
8 AM
1h 7m
10 AM
1h 1m
12 PM
1h 0m
3 PM
1h 1m
5 PM
1h 7m
8 PM
0h 55m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Monroe, CT
Wikimedia Commons
Middletown, CT
David Kanigan
Trip Overview
If you are looking to travel from Monroe to Middletown, you are in for a straightforward 39.9-mile journey across Connecticut. Expect to spend about 54 minutes behind the wheel, making this an ideal day trip that requires no overnight stops. With a modest fuel budget of approximately $6, this route is as economical as it is direct. You will navigate entirely via local roads rather than major interstates, keeping your travel within the Northeast region. It is a practical commute that provides a consistent, manageable pace for any driver.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Wilbur Cross Parkway | 21.2 mi | 25m |
| CT 66 | 5.5 mi | 9m |
| Leavenworth Road | 3.4 mi | 5m |
| Howe Avenue | 1.7 mi | 3m |
| Shelton Road | 1.6 mi | 2m |
| New Haven Avenue | 1.6 mi | 2m |
| Derby Turnpike | 1.3 mi | 1m |
| East Main Street | 1.1 mi | 1m |
Longest stretch:
Wilbur Cross Parkway
— 21.2 mi, about 25m
Turn-by-Turn Driving Directions
Step-by-step road directions between Monroe, CT and Middletown, CT.
1
Start on Fan Hill Road
382 ft
·
11 sec
·
Fan Hill Road
2
At end of road, turn right onto CT 111
0.2 mi
·
25 sec
·
Monroe Turnpike
3
Enter roundabout onto CT 110
218 ft
·
4 sec
·
Shelton Road
4
Continue on CT 110
1.6 mi
·
2 min
·
Shelton Road
5
Continue on CT 110
3.4 mi
·
5 min
·
Leavenworth Road
6
Continue on CT 110
1.7 mi
·
3 min
·
Howe Avenue
7
Turn left onto Bridge Street
0.2 mi
·
29 sec
·
Bridge Street
8
Turn right onto CT 34
0.5 mi
·
1 min
·
Main Street
9
Turn right onto Derby Avenue
0.3 mi
·
33 sec
·
Derby Avenue
Use the left / right lanes.
10
Continue on CT 34
1.6 mi
·
2 min
·
New Haven Avenue
11
Continue on CT 34
1.3 mi
·
1 min
·
Derby Turnpike
12
Take the exit
0.1 mi
·
26 sec
Toward CT 15 North: New Haven
13
Merge onto CT 15
21 mi
·
25 min
·
Wilbur Cross Parkway
Use the straight / right lanes.
14
Take the exit
0.3 mi
·
30 sec
Exit 64B
Toward East Main Street
Use the straight / slight right lanes.
15
Keep slight right at fork
247 ft
·
7 sec
Toward Industrial Area, Wesleyan
16
Turn slight right onto East Main Street
1.1 mi
·
1 min
·
East Main Street
Use the straight / right lanes.
17
Take the ramp
0.1 mi
·
19 sec
18
Merge onto CT 66
5.5 mi
·
9 min
·
CT 66
Use the straight / right lanes.
19
Arrive at destination
Washington Street
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Mid-route town
Meal stop
20 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 39.5 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 19.7 miles from Monroe, 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 115 decision points cluster between mile 0.1 and 32.6 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
0.1 mi into trip
|
~0m in
|
CT 111 / Monroe Turnpike
At end of road, turn right onto CT 111 / Monroe Turnpike
Navigation decision point
5
0.3 mi into trip
|
~0m in
|
CT 110 / Shelton Road
Enter roundabout onto CT 110 / Shelton Road
Roundabout - know your exit number before entering
5
11.1 mi into trip
|
~19m 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
32.3 mi into trip
|
~45m in
Take the exit toward East Main Street
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the straight / slight right lanes.
Exit 64B
Toward East Main Street
7
32.6 mi into trip
|
~45m in
Keep slight right at fork toward Industrial Area, Wesleyan
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Toward Industrial Area, Wesleyan
Fuel & Cost
Regular Gas
$6.36 one way
$12.72 round trip
$4.09/gal
25.4 MPG avg
14 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.50 | $7.00 | $13.99 |
| premium | $4.86 | $7.56 | $15.13 |
| diesel | $5.61 | $8.72 | $17.44 |
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
$6
Tolls
$0
Total
$6
Estimated CO2 emission: 13.8 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $4 in charging · 0 stops · 64% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 11.9 | 0 | $4.15 | $1.90 |
| Efficient EV | 9.9 | 0 | $3.46 | $1.58 |
| EV Truck/SUV | 15.8 | 0 | $5.53 | $2.53 |
Gas CO2
14 kg
EV CO2
5 kg (64% 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
Middletown, CT
Late night in Middletown on Sunday
Local time
3:54 AM
EDT
Current temp
42°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
13 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
57m 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 keeps you engaged from start to finish. You will primarily navigate via Monroe Turnpike, Shelton Road, and Leavenworth Road, meaning you won't encounter any highway driving during the entire 39.9-mile stretch. Because the route relies exclusively on local roads, you should anticipate a consistent rhythm rather than high-speed interstate cruising. This technical, winding path provides a distinct contrast to the monotonous, straight-line experience of major highway travel.
72% highway — fuel and pacing are the main things to plan.
19 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 21.2 mi on Wilbur Cross Parkway.
How Hard Is This Drive?
7/10
This is a straightforward highway drive that stays mostly on Wilbur Cross Parkway and CT 66. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 0.1 miles in near CT 111 / Monroe Turnpike.
Driving Effort
7/10
Focused - busy navigation packed into a short drive
Balances navigation complexity with total wheel time.
This is a short but busy drive. With 11 decision points packed into just 39.5 miles, you will need to pay attention to lane changes and exits — but the whole thing is over in 57m.
Where does it get tricky?
The main spots that need attention: at 0.1 miles (CT 111 / Monroe Turnpike): Navigation decision point; at 0.3 miles (CT 110 / Shelton Road): Roundabout - know your exit number before entering; at 11.1 miles (CT 15 / Wilbur Cross Parkway): Merge point - match speed before joining. Lane positioning matters here.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Monroe, CT and Middletown, CT, road signs point toward Industrial Area and Wesleyan.
Industrial Area
32.6 mi in
|
~45m
Wesleyan
32.6 mi in
|
~45m
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 57m. Total distance: 39.5 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
57m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (72%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 21.2 miles on Wilbur Cross Parkway. The full list of main roads is in the Roads section above.
Expect about $0.09 in tolls one way, starting with Derby Turnpike. Most Northeast and Midwest toll agencies accept E-ZPass; in the West and Texas, transponders like TxTag or FasTrak apply. If you do not have a transponder, cashless tolling plates will mail a bill to the vehicle's registered address — usually with a surcharge, so a rental-car toll pass is often cheaper than paying by mail.
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 Middletown, 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: at 0.1 miles (CT 111 / Monroe Turnpike): Navigation decision point; at 0.3 miles (CT 110 / Shelton Road): Roundabout - know your exit number before entering; at 11.1 miles (CT 15 / Wilbur Cross Parkway): Merge point - match speed before joining. Lane positioning matters here.
Yes. A round trip is manageable in a single day if you plan a break at Middletown, 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, and EIA for fuel prices. See our methodology for refresh cadence and limitations.
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