How far is Oyster Bay, NY from Ossining, NY?
The driving distance from Oyster Bay, NY to Ossining, NY is about 49.5 miles (79.7 km), with a travel time of about 01h 21m by car.
- The straight-line flight distance is about 26.8 miles (43.1 km).
- For a round trip, plan for roughly 02h 42m 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 01h 21m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
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.
Town in Westchester County, New York, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Chance Rain Showers
Slight Chance Rain Showers then Mostly Cloudy
Driving Route Map
The map below follows the saved road route between Oyster Bay and Ossining.
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay and Ossining.
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1
Start on Berry Hill Road
88 m · 20 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 right to continue on Throgs Neck Expressway
1.8 mi · 3 min · Throgs Neck Expressway
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12
Merge slight right onto Bruckner Expressway
1 mi · 2 min · Bruckner Expressway
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13
Continue on New England Thruway
1074 ft · 18 sec · New England Thruway
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14
Take the exit slight right toward Hutchinson Parkway North
131 m · 15 sec
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15
Keep slight left to continue on Hutchinson River Parkway North
912 ft · 31 sec
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16
Merge slight left onto Hutchinson River Parkway
3.8 mi · 6 min · Hutchinson River Parkway
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17
Take the exit slight right
618 ft · 24 sec
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18
Turn left onto Lincoln Avenue
1.2 km · 1 min · Lincoln Avenue
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19
Turn right onto North Columbus Avenue
2040 ft · 43 sec · North Columbus Avenue
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20
Take the ramp left toward Cross County Parkway West
1512 ft · 37 sec
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21
Merge slight left onto Cross County Parkway
3011 ft · 54 sec · Cross County Parkway
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22
Take the exit slight right toward Bronx Parkway, Sprain Parkway
653 ft · 19 sec
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23
Keep slight right to continue on Bronx Parkway North, Sprain Parkway
1980 ft · 1 min
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24
Merge slight left onto Bronx River Parkway
1714 ft · 33 sec · Bronx River Parkway
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25
Keep slight left to continue on Sprain Brook Parkway
12.6 mi · 17 min · Sprain Brook Parkway
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26
Continue on Taconic State Parkway
1.8 mi · 2 min · Taconic State Parkway
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27
Take the exit slight right toward NY 9A, NY 100 North
2593 ft · 1 min
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28
Continue straight
2.4 mi · 4 min
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29
Turn left onto Chappaqua Road
144 m · 15 sec · Chappaqua Road
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30
Turn straight onto Pleasantville Road
1.3 km · 2 min · Pleasantville Road
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31
At the end of the road, turn left onto Croton Avenue
1702 ft · 51 sec · Croton Avenue
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32
Continue on Upper Croton Avenue
2158 ft · 1 min · Upper Croton Avenue
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33
Arrive at your destination
0 m · 1 sec · Upper Croton Avenue
Car Route Details
A richer read on the saved driving route between Oyster Bay and Ossining.
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.
Northern Boulevard
Turn right onto Northern Boulevard
13.4 mi · 00h 23m
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.
Chance Rain Showers leaving Oyster Bay and Slight Chance Rain Showers then Mostly Cloudy near Ossining.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Oyster Bay to Ossining?
The road trip is about 49.5 miles (79.7 km) and usually takes 01h 21m 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?
Eastchester is a useful midpoint, sitting about 24.8 miles from Oyster Bay and 24.8 miles from Ossining.
How much longer is the road route than the straight-line distance?
The direct path is about 26.8 miles (43.1 km), while the road route adds roughly 22.7 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 3:48 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $7.02 one way or $14.03 round trip. Estimated CO2 is about 15.6 kg one way.
What should you check before leaving?
Before you leave, expect Chance Rain Showers around Oyster Bay and Slight Chance Rain Showers then Mostly Cloudy near Ossining.
Stop Ideas Near Eastchester
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Radio City Music Hall
#Artlook New York City Hall Wedding Photographer
CITY HALL LOBBY
Town Hall
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Eastchester.
Flight Path Map
This map shows the direct air route between Oyster Bay and Ossining. Straight-line distance: 26.77 mi (43.08 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 Ossining
Town in Westchester County, New York, United States
| Population | 37,551 |
| Coordinates | 41.1628700, -73.8615200 |
| Altitude | 49 |
| Country | United States |
End: Ossining (-73.86152, 41.16287)
Estimated Travel Time
Distance: 80 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 39m |
| 40 mph (64.37 km/h) | 01h 14m |
| 50 mph (80.47 km/h) | 00h 59m |
| 60 mph (96.56 km/h) | 00h 49m |
| 70 mph (112.65 km/h) | 00h 42m |
| 80 mph (129 km/h) | 00h 37m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.01 | $7.02 | $14.03 |
| Mid-grade | $4.48 | $7.84 | $15.68 |
| Premium | $4.86 | $8.51 | $17.01 |
| Diesel | $4.69 | $8.21 | $16.43 |
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 22, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.