How far is Windham, NY from Oyster Bay, NY?
The driving distance from Windham, NY to Oyster Bay, NY is about 165.8 miles (266.8 km), with a travel time of about 03h 05m by car.
- The straight-line flight distance is about 106.3 miles (171.1 km).
- For a round trip, plan for roughly 06h 10m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 AM EDT.
Reverse, save, or send this route
This drive is better planned with a longer stop or an overnight stay. Copy the route link, send it to another device, or print a clean version before you head out.
This drive is better planned with a longer stop or an overnight stay.
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 03h 05m.
An early departure helps you fit a real stop into the day without turning the return into a late-night drive.
You are leaving earlier than the recommended window, which gives you extra margin for breaks and traffic.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
City in New Windsor, New York, United States of America
Route Weather Snapshot
Check the forecast at both ends before you head out.
Widespread Frost then Sunny
Sunny
Driving Route Map
The map below follows the saved road route between Windham and Oyster Bay.
Turn-by-Turn Driving Directions
Step-by-step road directions between Windham and Oyster Bay.
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1
Start on State Highway 23
16.5 mi · 24 min · State Highway 23
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2
Turn right onto State Highway 32
9.2 mi · 14 min · State Highway 32
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3
Continue on King's Highway
6.8 mi · 9 min · King's Highway
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4
Take the ramp left
1369 ft · 34 sec
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5
Merge slight left onto New York State Thruway
70.5 mi · 1 hr 21 min · New York State Thruway
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6
Keep slight right to continue on I 287 South, NJ 17 South: New Jersey
1.5 km · 60 sec
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7
Continue straight
2496 ft · 39 sec
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8
Keep slight left to continue on NJ 17 South: Mahwah
14.1 mi · 19 min
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9
Take the exit slight right toward NJ 4, GSP South: Paterson, Fort Lee, New York
566 ft · 19 sec
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10
Keep slight left to continue on NJ 4 East: Fort Lee, New York
2455 ft · 1 min
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11
Merge slight left
1417 ft · 24 sec
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12
Continue straight
6.4 mi · 9 min
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13
Take the exit slight left toward I 95 North: George Washington Bridge
1124 ft · 18 sec
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14
Merge slight left
1.2 km · 55 sec
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15
Keep slight left
1.3 km · 1 min
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16
Continue on George Washington Bridge (upper level)
3174 ft · 1 min · George Washington Bridge (upper level)
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17
Continue on Trans-Manhattan Expressway
1.2 km · 1 min · Trans-Manhattan Expressway
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18
Continue on Cross Bronx Expressway
4.7 mi · 6 min · Cross Bronx Expressway
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19
Keep slight right to continue on Cross Bronx Expressway
2 mi · 3 min · Cross Bronx Expressway
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20
Merge slight left onto Throgs Neck Expressway
3271 ft · 58 sec · Throgs Neck Expressway
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21
Continue on Throgs Neck Bridge
2 mi · 3 min · Throgs Neck Bridge
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22
Continue on Clearview Expressway
2 mi · 2 min · Clearview Expressway
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23
Take the exit slight right toward NY 25A: Northern Boulevard
1133 ft · 32 sec
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24
Continue on Clearview Expressway
139 m · 18 sec · Clearview Expressway
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25
Turn left onto Northern Boulevard
14.5 mi · 25 min · Northern Boulevard
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26
Turn left onto Jericho Oyster Bay Road
1358 ft · 30 sec · Jericho Oyster Bay Road
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27
Turn straight onto Oyster Bay Road
2534 ft · 47 sec · Oyster Bay Road
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28
Keep slight left to continue on Oyster Bay Road
79 m · 4 sec · Oyster Bay Road
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29
Continue on Pine Hollow Road
1.4 km · 1 min · Pine Hollow Road
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30
Continue on South Street
32 m · 6 sec · South Street
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31
Turn right onto Berry Hill Road
34 m · 9 sec · Berry Hill Road
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32
Continue on Berry Hill Road
19 m · 3 sec · Berry Hill Road
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33
Arrive at your destination
0 m · 1 sec · Berry Hill Road
Car Route Details
A richer read on the saved driving route between Windham and Oyster Bay.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
New York State Thruway
Merge slight left onto New York State Thruway
70.5 mi · 01h 21m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A longer out-and-back drive
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
Widespread Frost then Sunny leaving Windham and Sunny near Oyster Bay.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Windham to Oyster Bay?
The road trip is about 165.8 miles (266.8 km) and usually takes 03h 05m in normal driving conditions.
Is this a same-day trip or an overnight route?
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
What is the halfway point on this route?
Vails Gate is a useful midpoint, sitting about 78.4 miles from Windham and 87.3 miles from Oyster Bay.
How much longer is the road route than the straight-line distance?
The direct path is about 106.3 miles (171.1 km), while the road route adds roughly 59.5 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 6:00 AM to 8:00 AM EDT. If you want a more comfortable same-day return, try to leave by 10:50 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $23.45 one way or $46.91 round trip. Estimated CO2 is about 52 kg one way.
What should you check before leaving?
Before you leave, expect Widespread Frost then Sunny around Windham and Sunny near Oyster Bay.
Stop Ideas Near Vails Gate
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 Vails Gate.
Poughkeepsie station
Croton–Harmon station
Rhinecliff–Kingston station
Yonkers station
Flight Path Map
This map shows the direct air route between Windham and Oyster Bay. Straight-line distance: 106.33 mi (171.12 km).
#1 Windham
Census-designated place in Greene County, New York, United States
| Population | 1,683 |
| Coordinates | 42.3073100, -74.2520900 |
| Altitude | 462 |
| Country | United States |
#2 Oyster Bay
Town on Long Island, New York, United States
| Population | 296,592 |
| Coordinates | 40.8656500, -73.5320700 |
| Altitude | 14 |
| Country | United States |
End: Berry Hill Road (-73.531924, 40.865647)
Estimated Travel Time
Distance: 267 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 05h 31m |
| 40 mph (64.37 km/h) | 04h 08m |
| 50 mph (80.47 km/h) | 03h 18m |
| 60 mph (96.56 km/h) | 02h 45m |
| 70 mph (112.65 km/h) | 02h 22m |
| 80 mph (129 km/h) | 02h 04m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.01 | $23.45 | $46.91 |
| Mid-grade | $4.48 | $26.21 | $52.43 |
| Premium | $4.86 | $28.44 | $56.87 |
| Diesel | $4.69 | $27.46 | $54.92 |
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 · May 12, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.