Origin
Westport, CT
Night in Westport on Friday
Local time
9:22 PM
EDT
Current temp
43°F
Unavailable
Live forecast
Trip from Westport, CT to Middletown, CT
Pin this tripCompiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Sep 5, 2026 · Editorial standards
Drive Time
1h 10m
Distance
51.3 mi
82 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$9
one way
EV Charging
Unknown
Best Time to Leave
4 AM
1h 5m
★
6 AM
1h 10m
8 AM
1h 21m
10 AM
1h 14m
12 PM
1h 13m
3 PM
1h 15m
5 PM
1h 21m
8 PM
1h 7m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Westport, CT
MART PRODUCTION
Middletown, CT
David Kanigan
Trip Overview
Westport, CT to Middletown, CT is 51.3 miles and takes about 1 hour 10 minutes via Wilbur Cross Parkway and CT 66, with a fuel budget near $9 and enough daylight to finish in a day. This trip stays within Connecticut, traveling from the Northeast region to the Northeast region. Given its short length and predominantly highway profile, this route is well-suited for a same-day excursion. You'll spend most of your time on parkways, so plan for a smooth, albeit somewhat limited, driving experience. It's a straightforward connection between two points in the state.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Wilbur Cross Parkway | 26.4 mi | 32m |
| Merritt Parkway | 15.9 mi | 21m |
| CT 66 | 5.5 mi | 9m |
| Main Street | 1.1 mi | 2m |
| East Main Street | 1.1 mi | 1m |
| Myrtle Avenue | 0.4 mi | <1m |
| Weston Road | 0.1 mi | <1m |
| Post Road East | <0.1 mi | <1m |
Longest stretch:
Wilbur Cross Parkway
— 26.4 mi, about 32m
Turn-by-Turn Driving Directions
Step-by-step road directions between Westport, CT and Middletown, CT.
1
Start on US 1
44 ft
·
3 sec
·
Post Road East
2
Turn right onto Myrtle Avenue
0.1 mi
·
15 sec
·
Myrtle Avenue
3
Continue on Myrtle Avenue
0.2 mi
·
29 sec
·
Myrtle Avenue
4
Turn right onto Main Street
1.1 mi
·
2 min
·
Main Street
Use the straight lane.
5
Turn slight left onto CT 57
0.1 mi
·
17 sec
·
Weston Road
6
Take the ramp
0.2 mi
·
24 sec
7
Merge onto CT 15
16 mi
·
21 min
·
Merritt Parkway
Use the straight / slight right lanes.
8
Continue on CT 15
26 mi
·
32 min
·
Wilbur Cross Parkway
Use the straight / slight right lanes.
9
Take the exit
0.3 mi
·
30 sec
Exit 64B
Toward East Main Street
Use the straight / slight right lanes.
10
Keep slight right at fork
247 ft
·
7 sec
Toward Industrial Area, Wesleyan
11
Turn slight right onto East Main Street
1.1 mi
·
1 min
·
East Main Street
Use the straight / right lanes.
12
Take the ramp
0.1 mi
·
19 sec
13
Merge onto CT 66
5.5 mi
·
9 min
·
CT 66
Use the straight / right lanes.
14
Arrive at destination
Washington Street
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
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 25.6 miles from Westport, 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 85 decision points cluster between mile 0.4 and 45.7 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
6
0.4 mi into trip
|
~0m in
|
Main Street
Turn right onto Main Street
Lane positioning matters here
Use the straight lane.
5
1.8 mi into trip
|
~3m in
|
CT 15 / Merritt Parkway
Merge onto CT 15 / Merritt Parkway
Merge point - match speed before joining. Lane positioning matters here
Use the straight / slight right lanes.
7
44.1 mi into trip
|
~57m 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
44.4 mi into trip
|
~58m 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
5
45.7 mi into trip
|
~1h in
|
CT 66
Merge onto CT 66
Merge point - match speed before joining. Lane positioning matters here
Use the straight / right lanes.
Fuel & Cost
Regular Gas
$8.55 one way
$17.09 round trip
$4.23/gal
25.4 MPG avg
18 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.70 | $9.48 | $18.96 |
| premium | $5.07 | $10.23 | $20.46 |
| diesel | $5.60 | $11.31 | $22.62 |
No toll roads detected on this route.
Drive Cost (one way)
Fuel
$9
Estimated CO2 emission: 17.9 kg one way. Prices: EIA weekly data, 2026-08-31.
Driving Electric?
About $5 in charging · 0 stops · 67% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 15.4 | 0 | $5.39 | $2.46 |
| Efficient EV | 12.8 | 0 | $4.49 | $2.05 |
| EV Truck/SUV | 20.5 | 0 | $7.18 | $3.28 |
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
Middletown, CT
Night in Middletown on Friday
Local time
9:22 PM
EDT
Current temp
71°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
28 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 10m 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?
This route is 93% highway, meaning you'll be on limited-access roads for the vast majority of the trip. You'll encounter a longest stretch of 26.4 miles on the Wilbur Cross Parkway. Surface roads like CT 66 come into play toward the end. Expect a consistent driving pace with few interruptions until you transition off the parkway.
93% highway — fuel and pacing are the main things to plan.
14 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 26.4 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 Merritt Parkway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 0.4 miles in near Main Street.
Driving Effort
7/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 51.3 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 0.4 miles (Main Street): Lane positioning matters here; at 1.8 miles (CT 15 / Merritt Parkway): Merge point - match speed before joining. Lane positioning matters here; at 44.1 miles: Exit ramp - move to the correct lane early. Lane positioning matters here.
Elevation Profile
Mostly flat terrain
420 ft
18 ft
Total Climb
929 ft
Total Descent
897 ft
Highest Point
420 ft
~48.3 mi in
Elevation Range
402 ft
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 Westport, CT and Middletown, CT, road signs point toward Industrial Area and Wesleyan.
Industrial Area
44.4 mi in
|
~58m
Wesleyan
44.4 mi in
|
~58m
About the Cities
Starting in Westport, CT
Full guide →Westport is in Fairfield County, Connecticut.
Top landmarks
- • Compo–Owenoke Historic District — human settlement in United States of America
- • Saugatuck River Bridge — bridge in Westport, Connecticut
- • Westport Bank and Trust Company — historic place
Arriving in Middletown, CT
Full guide →Founded 1651
Middletown is a a moderately-sized college and business town, with a few interesting remnants of 19th-century churches, graveyards, and mills. It is in Connecticut on the Connecticut River, about 20 miles (32 km) south of Hartford.
Top landmarks
- • St. Sebastian Church — Roman Catholic church in Middletown, Connecticut, part of the Diocese of Norwich
- • Metro South Historic District — historic district in Middletown, Connecticut, United States
- • Samuel Wadsworth Russell House — historic house in Connecticut, United States
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 10m. Total distance: 51.3 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 10m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (93%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 26.4 miles on Wilbur Cross Parkway. The full list of main roads is in the Roads section above.
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 0.4 miles (Main Street): Lane positioning matters here; at 1.8 miles (CT 15 / Merritt Parkway): Merge point - match speed before joining. Lane positioning matters here; at 44.1 miles: Exit ramp - move to the correct lane early. 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, EIA for fuel prices, and USGS 3DEP for elevation. See our methodology for refresh cadence and limitations.
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