This 89.3-mile drive from Middletown, NY, to Oyster Bay, NY, is designed for a single day, taking approximately 2 hours and 4 minutes. You'll navigate primarily on NY 17 and Northern Boulevard, with a segment on NJ 17, offering a mixed driving experience. With an estimated fuel cost of $15, this trip is quite economical for a day excursion within the Northeast region. The relatively short duration and manageable distance make it a convenient option for a quick getaway or a visit between these two New York locations.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
44.7 miles from Middletown, NY
A natural place for your longest stop of the day
, about 56m into the drive
.
Main Roads
Road
Distance
Duration
NY 17
18.5 mi
21m
Northern Boulevard
14.5 mi
24m
NJ 17
14.1 mi
18m
New York State Thruway
13.7 mi
15m
NJ 4
6.7 mi
9m
Cross Bronx Expressway
6.6 mi
8m
Clearview Expressway
2.1 mi
2m
Throgs Neck Bridge
2 mi
3m
Longest stretch:
NY 17
— 18.5 mi, about 21m
Turn-by-Turn Driving Directions
Step-by-step road directions between Middletown, NY and Oyster Bay, NY.
1
Start on Mill Street
81 ft·8 sec·Mill Street
2
Turn left onto West Main Street
0.1 mi·17 sec·West Main Street
3
Turn right onto Highland Avenue
0.1 mi·22 sec·Highland Avenue
4
Turn slight right onto NY 17M; NY 211
1.0 mi·1 min·Wickham Avenue
5
Continue on NY 211
1.3 mi·2 min·Route 211 East
Use the straight / right lanes.
6
Take the ramp
428 ft·11 sec
Toward NY 17 East: Goshen, New York CityUse the right lane.
7
Continue on this road
0.3 mi·33 sec·this road
Exit 121WToward I 84 West: ScrantonUse the right lane.
8
Merge onto NY 17
18 mi·20 min·NY 17
Use the straight / slight right lanes.
9
Keep slight left at fork
0.7 mi·59 sec
Toward I 87, NYST: Albany, New York CityUse the slight right lane.
10
Keep slight right at fork
0.9 mi·1 min
Toward I 87 Toll South: New York CityUse the slight right lane.
11
Merge onto I 87
14 mi·15 min·New York State Thruway
Use the straight / slight right lanes.
12
Keep slight right at fork onto NY 17
0.9 mi·59 sec·NY 17
Exit 15Toward I 287 South, NJ 17 South: New JerseyUse the slight right lane.
13
Continue on I 287; NJ 17
0.5 mi·39 sec·I 287; NJ 17
14
Keep slight left at fork onto NJ 17
14 mi·18 min·NJ 17
Exit 66Toward NJ 17 South: MahwahUse the slight left / straight lanes.
15
Take the exit
0.1 mi·19 sec
Toward NJ 4, GSP South: Paterson, Fort Lee, New York
16
Keep slight left at fork
0.5 mi·1 min
Toward NJ 4 East: Fort Lee, New York
17
Merge onto NJ 4
0.3 mi·24 sec·NJ 4
Use the right lane.
18
Continue on NJ 4
6.4 mi·8 min·NJ 4
Use the straight / slight right lanes.
19
Take the exit
0.2 mi·18 sec
Toward I 95 North: George Washington BridgeUse the straight / slight left lanes.
20
Merge onto I 95 EXPR
0.7 mi·54 sec·I 95 EXPR
Use the straight / slight right lanes.
21
Keep slight left at fork onto I 95 EXPR
0.8 mi·1 min·I 95 EXPR
22
Continue on I 95; US 1; US 9
0.6 mi·1 min·George Washington Bridge (upper level)
Use the straight / slight right lanes.
23
Continue on I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
24
Continue on I 95; US 1
4.7 mi·6 min·Cross Bronx Expressway
Use the straight / slight right lanes.
25
Keep slight right at fork onto I 295
2.0 mi·2 min·Cross Bronx Expressway
Exit 6BToward I 295 South: Throgs Neck BridgeUse the straight / slight left lanes.
26
Merge onto I 295
0.6 mi·58 sec·Throgs Neck Expressway
27
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
Use the straight / slight right lanes.
28
Continue on I 295
2.0 mi·2 min·Clearview Expressway
Use the straight / slight right lanes.
29
Take the exit
0.2 mi·32 sec
Exit 5Toward NY 25A: Northern BoulevardUse the straight / slight right lanes.
30
Continue on Clearview Expressway
457 ft·17 sec·Clearview Expressway
31
Turn left onto NY 25A
15 mi·24 min·Northern Boulevard
Use the left lane.
32
Turn left onto NY 106
0.3 mi·29 sec·Jericho Oyster Bay Road
33
Turn straight onto NY 106
0.5 mi·46 sec·Oyster Bay Road
34
Keep slight left at fork onto NY 106
260 ft·4 sec·Oyster Bay Road
35
Continue on NY 106
0.9 mi·1 min·Pine Hollow Road
Use the left lane.
36
Continue on NY 106
105 ft·5 sec·South Street
37
Turn right onto Berry Hill Road
112 ft·9 sec·Berry Hill Road
38
Continue on Berry Hill Road
64 ft·2 sec·Berry Hill Road
39
Arrive at destination
Berry Hill Road
Trip Plan
Given the 2-hour duration, this route is comfortably completed in one day. Consider departing Middletown, NY, in the morning to allow for a full day at your destination in Oyster Bay, NY. With a fuel cost of around $15, you won't need frequent, costly stops, but keep an eye on your fuel gauge, especially before heading into potentially less developed stretches. The longest stretch of 18.5 miles on NY 17 means you can cover a significant portion of the distance without a major break, but plan for a brief stop if needed before the final leg.
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 44.7 miles from Middletown, NY, or about 56m into the drive.
The longest continuous stretch on this route runs about 18.5 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 25m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 44.7 miles or 56m 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 41m
Traffic, exits, and arrival timing usually matter more near Oyster Bay, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Middletown, 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 Middletown, NY
This is one driving day of about 89.3 miles and 2h 4m.
Your first comfortable stop window is around 20 miles from Middletown, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on NY 17 for about 18.5 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 23
5 decision points cluster between mile 20.5 and 66.2 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
8
20.5 mi into trip|~26m in
Keep slight left at fork toward I 87, NYST: Albany, New York City
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Toward I 87, NYST: Albany, New York City
7
21.1 mi into trip|~27m in
Keep slight right at fork toward I 87 Toll South: New York City
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Toward I 87 Toll South: New York City
9
35.7 mi into trip|~44m in|NY 17
Keep slight right at fork onto NY 17 toward I 287 South, NJ 17 South: New Jersey
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 15
Toward I 287 South, NJ 17 South: New Jersey
8
37.1 mi into trip|~46m in|NJ 17
Keep slight left at fork onto NJ 17 toward NJ 17 South: Mahwah
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / straight lanes.
Exit 66
Toward NJ 17 South: Mahwah
8
66.2 mi into trip|~1h 26m in|I 295 / Cross Bronx Expressway
Keep slight right at fork onto I 295 / Cross Bronx Expressway toward I 295 South: Throgs Neck Bridge
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight left lanes.
Exit 6B
Toward I 295 South: Throgs Neck Bridge
Fuel & Cost
Regular Gas
$14.70 one way
$29.40 round trip
$4.18/gal25.4 MPG avg31 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$15.89
$31.79
premium
$4.92
$17.31
$34.62
diesel
$5.61
$19.72
$39.43
Estimated Tolls: $23.23
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
New York State Thruway
(13.7 mi)$0.68
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
$63–$88
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 31.2 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
26.8
0
$9.38
$4.29
Efficient EV
22.3
0
$7.81
$3.57
EV Truck/SUV
35.7
0
$12.50
$5.72
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 15, 2026
Origin
Middletown, NY
Morning
in Middletown on Sunday
Local time
6:06 AM
EDT
Current temp
41°F
Unavailable
Live forecast
Destination
Oyster Bay, NY
Morning
in Oyster Bay on Sunday
Local time
6:06 AM
EDT
Current temp
45°F
Unavailable
Live forecast
49°F
Ramapo, NY
45 mi in
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 warmer 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.
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
~22 min detour
Free
near mile 65.5
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 65.5
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 65.5
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 65.5
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a mixed drive on this 89.3-mile journey, with 59% of it on highways. The longest uninterrupted stretch you'll encounter is 18.5 miles along NY 17, providing a good opportunity for steady progress. As you transition from NY 17 to Northern Boulevard and NJ 17, the character of the road will likely shift, blending faster-paced sections with potentially more local or suburban road conditions. This variability keeps the drive engaging without being overly demanding.
59% highway, the rest on surface roads — varied driving throughout.
39 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 18.5 mi on NY 17.
How Hard Is This Drive?
10/10
This route mixes highway mileage with some local-road sections near the start or finish. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 20.5 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 23 significant decision points across 89.3 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 20.5 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 21.1 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 35.7 miles (NY 17): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Middletown, NY and Oyster Bay, NY, road signs point toward Nyst: Albany, New York City, Gsp South: Paterson, Fort Lee and New York.
Oyster Bay is one of three towns in Nassau County, on Long Island, New York.
The town of Oyster Bay comprises a large portion of eastern Nassau County and includes a slew of villages and other communities. This article covers North Oyster Bay – the area closest to Oyster Bay itself (in other words, everything that is north of the Long Island Expressway). See South Oyster Bay for the southern half of the town (in other words, the area south of the expressway). See the article for Glen Cove for communities in the northwest part of the town that are closest to that city.
Top landmarks
•Christ Church — historic Episcopal parish in Oyster Bay, New York, USA
Doable as a same-day drive at 2h 4m. Total distance: 89.3 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 (59%). Some complex stretches to watch for.
Scenic Drive
Mixed highway & surface route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 18.5 miles on NY 17. The full list of main roads is in the Roads section above.
Expect about $23.23 in tolls one way, starting with George Washington Bridge. 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 Oyster Bay, NY before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 20.5 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 21.1 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 35.7 miles (NY 17): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — Hamilton Grange National Memorial, General Grant National Memorial and Stonewall National Monument (6 total within detour distance). See the National Parks section for detour distances and tips on detours.
Yes. A round trip is manageable in a single day if you plan a break at Oyster Bay, NY before heading back.
