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 NY 17, NJ 17, Northern Boulevard for much of the mileage,
and the overall profile is highway-focused drive.
The longest uninterrupted segment is about 27.1 miles on NY 17.
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 7m into the drive
.
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 (74%). Some complex stretches to watch for.
Drive Character
This is a 2h 4m highway drive covering 88.7 miles, with most of the trip on NY 17 and NJ 17. The longest continuous stretch is about 27.1 miles on NY 17.
Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 37 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
NY 17 is the longest continuous segment at about 27.1 miles.
How Hard Is This Drive?
This is a straightforward highway drive that stays mostly on NY 17 and NJ 17. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 17.6 miles in.
Driving Effort10/10
High effort - long or complex enough to need steady focus all day
Balances navigation complexity with total wheel time.
This is a demanding drive. With 22 significant decision points across 88.7 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 17.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 29.8 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 30.1 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Critical Maneuvers
5 of 22 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
8
17.6 mi into trip|~29m in
Take the exit toward I 295 North: Throgs Neck Bridge, Bronx, New England
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 33
Toward I 295 North: Throgs Neck Bridge, Bronx,...
8
29.8 mi into trip|~47m in
Take the exit toward I 95 South, NJTP South: Hackensack
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 95 South, NJTP South: Hackensack
9
30.1 mi into trip|~48m in
Keep slight right at fork toward NJ 4 West: Paramus
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / slight right lanes.
Exit 72A
Toward NJ 4 West: Paramus
8
37.1 mi into trip|~57m in
Keep slight right at fork toward NJ 17 North: Mahwah
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Toward NJ 17 North: Mahwah
8
66.5 mi into trip|~1h 33m in
Take the exit toward US 6, NY 17: Harriman
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 16
Toward US 6, NY 17: Harriman
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Oyster Bay, NY and Middletown, NY, road signs point toward Cross Island Parkway North, Bronx, New England, Upper Level, Njtp South: Hackensack and Gsp South - among others.
Cross Island Parkway North
15.1 mi in|~25m
Bronx
17.6 mi in|~29m
New England
17.6 mi in|~29m
Upper Level
27.3 mi in|~43m|via I 95; US 1
Njtp South: Hackensack
29.8 mi in|~47m
Gsp South
36.9 mi in|~57m
Gsp North
36.9 mi in|~57m
Newark
36.9 mi in|~57m
Mahwah
36.9 mi in|~57m
New York State Thruway North: Albany
52.2 mi in|~1h 17m|via NY 17
Port Jervis
81.2 mi in|~1h 52m|via US 6; NY 17M
Main Roads
Road
Distance
Duration
NY 17
27.1 mi
31m
NJ 17
14.7 mi
18m
Northern Boulevard
13.4 mi
22m
NJ 4
6.7 mi
9m
Cross Bronx Expressway
6.6 mi
8m
US 6
5.5 mi
8m
Cross Island Parkway
2.3 mi
3m
Throgs Neck Bridge
1.8 mi
3m
Longest stretch:
NY 17
— 27.1 mi, about 31m
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay, NY and Middletown, NY.
1
Start on Berry Hill Road
288 ft·21 sec·Berry Hill Road
2
Turn sharp left onto NY 106
429 ft·9 sec·South Street
3
Continue on NY 106
0.9 mi·1 min·Pine Hollow Road
4
Continue on NY 106
0.7 mi·1 min·Oyster Bay Road
5
Turn right onto NY 25A
13 mi·22 min·Northern Boulevard
Use the left lane.
6
Take the ramp
0.2 mi·28 sec
Toward Cross Island Parkway North, Whitestone BridgeUse the right lane.
7
Merge onto CI
2.3 mi·3 min·Cross Island Parkway
Use the straight / slight right lanes.
8
Take the exit
0.6 mi·1 min
Exit 33Toward I 295 North: Throgs Neck Bridge, Bronx, New EnglandUse the straight / slight right lanes.
9
Merge onto I 295
1.8 mi·3 min·Throgs Neck Bridge
10
Continue on I 295
0.7 mi·1 min·Throgs Neck Expressway
Use the straight / slight right lanes.
11
Keep slight left at fork onto I 295
6.6 mi·8 min·Cross Bronx Expressway
Use the straight / slight right lanes.
12
Keep slight left at fork onto I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
Toward Upper Level
13
Continue on I 95; US 1
0.6 mi·59 sec·George Washington Bridge (upper level)
14
Continue on I 95 EXPR; US 1 EXPR; US 9 EXPR
0.5 mi·48 sec·I 95 EXPR; US 1 EXPR; US 9 EXPR
15
Keep slight left at fork onto I 95 EXPR; US 1 EXPR; US 9 EXPR
0.6 mi·39 sec·I 95 EXPR; US 1 EXPR; US 9 EXPR
Use the straight / slight right lanes.
16
Keep slight left at fork onto I 95 EXPR; NJTP
0.1 mi·8 sec·I 95 EXPR; NJTP
17
Take the exit
0.2 mi·22 sec
Toward I 95 South, NJTP South: HackensackUse the straight / slight right lanes.
18
Keep slight right at fork
0.2 mi·23 sec
Exit 72AToward NJ 4 West: ParamusUse the slight left / slight right lanes.
19
Merge onto NJ 4
6.7 mi·9 min·NJ 4
Use the slight right lane.
20
Take the exit
0.2 mi·26 sec
Toward GSP South, NJ 17 South, GSP North, NJ 17 North: Grand State Plaza, Newark, MahwahUse the straight lane.
21
Keep slight right at fork
0.2 mi·36 sec
Toward NJ 17 North: MahwahUse the straight / slight right lanes.
22
Merge onto NJ 17
3.3 mi·4 min·NJ 17
Use the straight / slight right lanes.
23
Continue on NJ 17
7.3 mi·9 min·NJ 17
Use the straight / right lanes.
24
Continue on NJ 17
0.7 mi·50 sec·NJ 17
25
Continue on NJ 17
3.3 mi·4 min·NJ 17
26
Continue on I 287; NY 17
0.2 mi·10 sec·I 287; NY 17
27
Keep slight left at fork onto NY 17
14 mi·16 min·NY 17
Toward I 87 North, NY 17 North, New York State Thruway North: Albany
28
Take the exit
1.5 mi·3 min
Exit 16Toward US 6, NY 17: HarrimanUse the slight right lane.
29
Continue on this road
152 ft·3 sec·this road
Use the straight / slight right lanes.
30
Keep slight left at fork
0.4 mi·30 sec
Toward NY 17 West: BinghamtonUse the straight / slight right lanes.
31
Continue on NY 17
13 mi·14 min·NY 17
32
Take the exit onto US 6; NY 17M
5.5 mi·8 min·US 6; NY 17M
Exit 123Toward US 6, NY 17M: Middletown, Port Jervis
33
Continue on NY 17M
1.5 mi·2 min·NY 17M
Use the straight / right lanes.
34
Turn left onto NY 17M
0.4 mi·34 sec·Fulton Street
Use the left lane.
35
Turn slight right onto Harding Street
92 ft·5 sec·Harding Street
36
Turn right onto Mill Street
0.2 mi·37 sec·Mill Street
37
Arrive at destination
Mill Street
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 7m into the drive.
The longest continuous stretch on this route runs about 27.1 miles.
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 34m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 44.4 miles or 1h 7m 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.
The longest stretch is on NY 17 for about 27.1 miles.
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 7m into the drive
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.
National Parks Near This Route
Worth a detour if your schedule allows.
Hamilton Grange National Memorial
National Memorial
Merchant’s clerk, Revolutionary War soldier, first Secretary Treasury of the United States: Alexander Hamilton’s life is memorialized at The Grange, the home he built on a country estate in uptown Man...
The final resting place of President Ulysses S. Grant and his wife, Julia, is the largest mausoleum in North America. It testifies to a people’s gratitude for the man who ended the bloodiest conflict...
Before the 1960s, almost everything about living authentically as a lesbian, a bisexual person or a gay man was illegal. The Stonewall Uprising on June 28, 1969 is a milestone in the quest for civil r...
9 mi from route
~21 min detour
Free
near mile 27.5
The African Burial Ground stands as the oldest and largest known excavated burial site in North America for both free and enslaved Africans. It offers a profound testament to the enduring legacy of Af...
10 mi from route
~25 min detour
Free
near mile 27.5
Here at Federal Hall, George Washington took the oath of office as the first President of the United States, marking the beginning of the American constitutional republic. This historic site served as...
10 mi from route
~26 min detour
Free
near mile 27.5
Located at the southern tip of Manhattan, Castle Clinton marks the place where New York City began and reflects the growth of both the city and the nation. Built to defend the harbor during the War of...
11 mi from route
~27 min detour
Free
near mile 27.5
Park data from the National Park Service API. Alerts update every 2 hours.
Fuel & Cost
Regular Gas
$14.60 one way
$29.20 round trip
$4.18/gal25.4 MPG avg31 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: $22.55
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
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
$23
Meals
$25–$50
Total
$62–$87
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.
Forecast as of Apr 16, 2026
Origin
Oyster Bay, NY
Evening
in Oyster Bay on Friday
Local time
6:06 PM
EDT
Current temp
45°F
Unavailable
Live forecast
Destination
Middletown, NY
Evening
in Middletown on Friday
Local time
6:06 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 NY 17, NJ 17, Northern Boulevard. Most of the drive stays on highways, so watch for ramps and exits.
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.
This is a demanding drive. With 22 significant decision points across 88.7 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
The main spots that need attention: at 17.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 29.8 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 30.1 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Between Oyster Bay, NY and Middletown, NY, road signs point toward Cross Island Parkway North, Bronx, New England, Upper Level, Njtp South: Hackensack and Gsp South - among others.
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, EIA for fuel prices, and NPS for national parks. See our methodology for refresh cadence and limitations.
