Origin
Oyster Bay, NY
Afternoon in Oyster Bay on Friday
Local time
2:11 PM
EDT
Current temp
45°F
Unavailable
Live forecast
Trip from Oyster Bay, NY to Middletown, NY
Compiled and reviewed by the Trip.ovh planning team at COD Solutions Oy · Last reviewed Apr 17, 2026 · Editorial standards
Drive Time
2h 4m
Distance
88.7 mi
143 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$15
one way
EV Charging
Unknown
Best Time to Leave
4 AM
1h 56m
★
6 AM
2h 4m
8 AM
2h 22m
10 AM
2h 11m
12 PM
2h 9m
3 PM
2h 11m
5 PM
2h 21m
8 PM
1h 59m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Oyster Bay, NY
Wikimedia Commons
Middletown, NY
Wikimedia Commons
Trip Overview
The drive from Oyster Bay, NY to Middletown, NY covers 88.7 miles and takes about 2h 4m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on South Street, Pine Hollow Road, Oyster Bay Road for much of the mileage, and the overall profile is turn-heavy local drive. At current regular gas prices, budget about $14.60 one way before food or hotel costs.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
44.4 miles from Oyster Bay, NY
A natural place for your longest stop of the day , about 1h 2m into the drive .
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 2h 4m. Total distance: 88.7 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
2h 4m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (0%). Straightforward navigation.
Scenic Drive
Turn-heavy local drive route profile.
Drive Character
Expect a 2h 4m drive with frequent turns across 88.7 miles of local and secondary roads.
This route has more turning and local-road decision points than a simple highway run.
There are about 37 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
South Street is one of the defining roads on this drive.
How Hard Is This Drive?
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. Navigation is very simple - set it and forget it for most of the drive.
Driving Effort
1/10
Very easy - short and simple to drive
Balances navigation complexity with total wheel time.
The drive from Oyster Bay, NY to Middletown, NY is easy. At 2h 4m with 0% highway, most drivers will find it relaxed and low-stress.
Where does it get tricky?
This route does not have any notably tricky sections. Most of the drive from Oyster Bay, NY to Middletown, NY is straightforward, with well-signed roads and simple exits.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| South Street | — | — |
| Pine Hollow Road | — | — |
| Oyster Bay Road | — | — |
| Northern Boulevard | — | — |
| Cross Island Parkway North | — | — |
| Cross Island Parkway | — | — |
| I 295 North | — | — |
| Throgs Neck Bridge | — | — |
Some road-level metrics are being recalculated.
Longest stretch:
South Street
— detailed segment metrics are refreshing.
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay, NY and Middletown, NY.
1
Start on Berry Hill Road
289 ft
·
21 sec
·
Berry Hill Road
2
Turn sharp left onto South Street
430 ft
·
9 sec
·
South Street
3
Continue on Pine Hollow Road
0.9 mi
·
1 min
·
Pine Hollow Road
4
Continue on Oyster Bay Road
0.7 mi
·
1 min
·
Oyster Bay Road
5
Turn right onto Northern Boulevard
13 mi
·
22 min
·
Northern Boulevard
6
Take the ramp right toward Cross Island Parkway North, Whitestone Bridge
0.2 mi
·
29 sec
·
Cross Island Parkway North, Whitestone Bridge
7
Merge slight left onto Cross Island Parkway
2.3 mi
·
3 min
·
Cross Island Parkway
8
Take the exit slight right toward I 295 North: Throgs Neck Bridge, Bronx, New England
0.6 mi
·
1 min
·
I 295 North: Throgs Neck Bridge, Bronx, New England
9
Merge slight left onto Throgs Neck Bridge
1.8 mi
·
3 min
·
Throgs Neck Bridge
10
Continue on Throgs Neck Expressway
0.7 mi
·
1 min
·
Throgs Neck Expressway
11
Keep slight left to continue on Cross Bronx Expressway
6.6 mi
·
8 min
·
Cross Bronx Expressway
12
Keep slight left to continue on Trans-Manhattan Expressway
0.7 mi
·
1 min
·
Trans-Manhattan Expressway
13
Continue on George Washington Bridge (upper level)
0.6 mi
·
1 min
·
George Washington Bridge (upper level)
14
Continue straight
0.5 mi
·
48 sec
15
Keep slight left
0.6 mi
·
39 sec
16
Keep slight left
0.1 mi
·
9 sec
17
Take the exit slight right toward I 95 South, NJTP South: Hackensack
0.2 mi
·
23 sec
·
I 95 South, NJTP South: Hackensack
18
Keep slight right to continue on NJ 4 West: Paramus
0.2 mi
·
24 sec
·
NJ 4 West: Paramus
19
Merge slight right
6.7 mi
·
9 min
20
Take the exit straight toward GSP South, NJ 17 South, GSP North, NJ 17 North: Grand State Plaza, Newark, Mahwah
0.2 mi
·
26 sec
·
GSP South, NJ 17 South, GSP North, NJ 17 North: Grand State Plaza, Newark, Mahwah
21
Keep slight right to continue on NJ 17 North: Mahwah
0.2 mi
·
37 sec
·
NJ 17 North: Mahwah
22
Merge slight left
3.3 mi
·
4 min
23
Continue straight
7.3 mi
·
9 min
24
Continue straight
0.7 mi
·
50 sec
25
Continue straight
3.3 mi
·
4 min
26
Continue straight
0.2 mi
·
11 sec
27
Keep slight left to continue on I 87 North, NY 17 North, New York State Thruway North: Albany
14 mi
·
16 min
·
I 87 North, NY 17 North, New York State Thruway North: Albany
28
Take the exit slight right toward US 6, NY 17: Harriman
1.5 mi
·
3 min
·
US 6, NY 17: Harriman
29
Continue straight
151 ft
·
4 sec
30
Keep slight left to continue on NY 17 West: Binghamton
0.4 mi
·
30 sec
·
NY 17 West: Binghamton
31
Continue straight
13 mi
·
14 min
32
Take the exit slight right toward US 6, NY 17M: Middletown, Port Jervis
5.5 mi
·
8 min
·
US 6, NY 17M: Middletown, Port Jervis
33
Continue straight
1.5 mi
·
2 min
34
Turn left onto Fulton Street
0.4 mi
·
35 sec
·
Fulton Street
35
Turn slight right onto Harding Street
92 ft
·
6 sec
·
Harding Street
36
Turn right onto Mill Street
0.2 mi
·
38 sec
·
Mill Street
37
Arrive at your destination
Trip Plan
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 44.4 miles from Oyster Bay, NY, or about 1h 2m into the drive.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 20 miles or 28m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 44.4 miles or 1h 2m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 45m
Traffic, exits, and arrival timing usually matter more near Middletown, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Oyster Bay, NY so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Oyster Bay, NY
This is one driving day of about 88.7 miles and 2h 4m.
Your first comfortable stop window is around 20 miles from Oyster Bay, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 44.4 mi from Oyster Bay, NY · 1h 2m into the drive
Mid-route town
Meal stop
44 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 20 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 44.4 miles from Oyster Bay, NY, which is a good place for a longer meal and fuel stop.
Arriving in Middletown, NY
The final approach into Middletown, NY usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Middletown, NY.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Fuel & Cost
Regular Gas
$14.60 one way
$29.20 round trip
$4.18/gal
25.4 MPG avg
31 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.52 | $15.79 | $31.58 |
| premium | $4.92 | $17.19 | $34.38 |
| diesel | $5.61 | $19.58 | $39.17 |
Estimated Tolls: $29.10
George Washington Bridge
$16.00
Whitestone Bridge
$6.55
Throgs Neck Bridge
$6.55
New York State Thruway
$0.00
Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.
Estimated Trip Cost (one way, 1 person)
Fuel
$15
Tolls
$29
Meals
$25–$50
Total
$69–$94
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 31 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $9 in charging · 0 stops · 68% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 26.6 | 0 | $9.31 | $4.26 |
| Efficient EV | 22.2 | 0 | $7.76 | $3.55 |
| EV Truck/SUV | 35.5 | 0 | $12.42 | $5.68 |
Gas CO2
31 kg
EV CO2
10 kg (68% 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, NY
Afternoon in Middletown on Friday
Local time
2:11 PM
EDT
Current temp
41°F
Unavailable
Live forecast
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
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
4 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
2h 4m 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 Oyster Bay, NY to Middletown, NY covers 88.7 miles and takes about 2h 4m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are South Street, Pine Hollow Road, Oyster Bay Road. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 44.4 miles from Oyster Bay, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $14.60 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.
The drive from Oyster Bay, NY to Middletown, NY is easy. At 2h 4m with 0% highway, most drivers will find it relaxed and low-stress.
This route does not have any notably tricky sections. Most of the drive from Oyster Bay, NY to Middletown, NY is straightforward, with well-signed roads and simple exits.
The route from Oyster Bay, NY to Middletown, NY does not surface many named destination signs beyond the main corridor.
How this page is built
Compiled by the Trip.ovh 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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