How far is Oyster Bay, NY from Middletown, NY?
The driving distance from Oyster Bay, NY to Middletown, NY is about 88.7 miles (142.8 km), with a travel time of about 02h 04m by car.
- The straight-line flight distance is about 61.3 miles (98.6 km).
- For a round trip, plan for roughly 04h 08m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 02h 04m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
This departure sits inside the recommended comfort window for the route.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Census-designated place in Rockland County, New York
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny then Slight Chance Showers And Thunderstorms
Partly Sunny then Slight Chance Showers And Thunderstorms
Driving Route Map
The map below follows the saved road route between Oyster Bay and Middletown.
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay and Middletown.
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1
Start on Berry Hill Road
88 m · 21 sec · Berry Hill Road
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2
Turn sharp left onto South Street
131 m · 9 sec · South Street
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3
Continue on Pine Hollow Road
1.4 km · 1 min · Pine Hollow Road
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4
Continue on Oyster Bay Road
1.2 km · 1 min · Oyster Bay Road
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5
Turn right onto Northern Boulevard
13.4 mi · 23 min · Northern Boulevard
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6
Take the ramp right toward Cross Island Parkway North, Whitestone Bridge
1178 ft · 29 sec
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7
Merge slight left onto Cross Island Parkway
2.3 mi · 3 min · Cross Island Parkway
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8
Take the exit slight right toward I 295 North: Throgs Neck Bridge, Bronx, New England
2905 ft · 1 min
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9
Merge slight left onto Throgs Neck Bridge
1.8 mi · 3 min · Throgs Neck Bridge
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10
Continue on Throgs Neck Expressway
1.1 km · 1 min · Throgs Neck Expressway
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11
Keep slight left to continue on Cross Bronx Expressway
6.6 mi · 9 min · Cross Bronx Expressway
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12
Keep slight left to continue on Trans-Manhattan Expressway
1.1 km · 1 min · Trans-Manhattan Expressway
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13
Continue on George Washington Bridge (upper level)
3167 ft · 60 sec · George Washington Bridge (upper level)
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14
Continue straight
2659 ft · 48 sec
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15
Keep slight left
3214 ft · 39 sec
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16
Keep slight left
559 ft · 9 sec
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17
Take the exit slight right toward I 95 South, NJTP South: Hackensack
1270 ft · 23 sec
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18
Keep slight right to continue on NJ 4 West: Paramus
970 ft · 24 sec
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19
Merge slight right
6.7 mi · 9 min
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20
Take the exit straight toward GSP South, NJ 17 South, GSP North, NJ 17 North: Grand State Plaza, Newark, Mahwah
951 ft · 26 sec
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21
Keep slight right to continue on NJ 17 North: Mahwah
1302 ft · 37 sec
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22
Merge slight left
3.3 mi · 4 min
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23
Continue straight
7.3 mi · 10 min
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24
Continue straight
1.2 km · 50 sec
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25
Continue straight
3.3 mi · 4 min
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26
Continue straight
877 ft · 11 sec
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27
Keep slight left to continue on I 87 North, NY 17 North, New York State Thruway North: Albany
14.3 mi · 16 min
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28
Take the exit slight right toward US 6, NY 17: Harriman
1.5 mi · 3 min
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29
Continue straight
46 m · 4 sec
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30
Keep slight left to continue on NY 17 West: Binghamton
2294 ft · 30 sec
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31
Continue straight
12.8 mi · 15 min
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32
Take the exit slight right toward US 6, NY 17M: Middletown, Port Jervis
5.5 mi · 8 min
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33
Continue straight
1.5 mi · 2 min
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34
Turn left onto Fulton Street
2053 ft · 35 sec · Fulton Street
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35
Turn slight right onto Harding Street
28 m · 6 sec · Harding Street
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36
Turn right onto Mill Street
863 ft · 38 sec · Mill Street
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37
Arrive at your destination
0 m · 1 sec · Mill Street
Car Route Details
A richer read on the saved driving route between Oyster Bay and Middletown.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
I 87 North
Keep slight left to continue on I 87 North, NY 17 North, New York State Thruway North: Albany
14.3 mi · 00h 16m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Mostly Sunny then Slight Chance Showers And Thunderstorms leaving Oyster Bay and Partly Sunny then Slight Chance Showers And Thunderstorms near Middletown.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Oyster Bay to Middletown?
The road trip is about 88.7 miles (142.8 km) and usually takes 02h 04m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Pearl River is a useful midpoint, sitting about 44.3 miles from Oyster Bay and 44.4 miles from Middletown.
How much longer is the road route than the straight-line distance?
The direct path is about 61.3 miles (98.6 km), while the road route adds roughly 27.4 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 2:22 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $12.55 one way or $25.10 round trip. Estimated CO2 is about 27.8 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny then Slight Chance Showers And Thunderstorms around Oyster Bay and Partly Sunny then Slight Chance Showers And Thunderstorms near Middletown.
Stop Ideas Near Pearl River
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Pearl River.
Yonkers station
Croton–Harmon station
New Rochelle station
Pennsylvania Station
Flight Path Map
This map shows the direct air route between Oyster Bay and Middletown. Straight-line distance: 61.28 mi (98.62 km).
#1 Oyster Bay
Town on Long Island, New York, United States
| Population | 296,592 |
| Coordinates | 40.8656500, -73.5320700 |
| Altitude | 14 |
| Country | United States |
#2 Middletown
City in Orange County, New York, United States
| Population | 28,023 |
| Coordinates | 41.4459300, -74.4229300 |
| Altitude | 170 |
| Country | United States |
End: Middletown (-74.42293, 41.44593)
Estimated Travel Time
Distance: 143 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 57m |
| 40 mph (64.37 km/h) | 02h 13m |
| 50 mph (80.47 km/h) | 01h 46m |
| 60 mph (96.56 km/h) | 01h 28m |
| 70 mph (112.65 km/h) | 01h 16m |
| 80 mph (129 km/h) | 01h 06m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.01 | $12.55 | $25.10 |
| Mid-grade | $4.48 | $14.03 | $28.05 |
| Premium | $4.86 | $15.21 | $30.43 |
| Diesel | $4.69 | $14.69 | $29.38 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in New York · Apr 15, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.