How far is Sheepshead Bay, NY from Ossining, NY?
The driving distance from Sheepshead Bay, NY to Ossining, NY is about 49 miles (78.9 km), with a travel time of about 01h 21m by car.
- The straight-line flight distance is about 39.7 miles (63.9 km).
- For a round trip, plan for roughly 02h 43m 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.
Sunny
Sunny
Driving Route Map
The map below follows the saved road route between Sheepshead Bay and Ossining.
Turn-by-Turn Driving Directions
Step-by-step road directions between Sheepshead Bay and Ossining.
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1
Start on Avenue Y
1203 ft · 1 min · Avenue Y
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2
Turn left onto Nostrand Avenue
1.7 mi · 4 min · Nostrand Avenue
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3
Turn right onto Kings Highway
1886 ft · 42 sec · Kings Highway
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4
Continue on Kings Highway
3.2 mi · 6 min · Kings Highway
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5
Continue on Tapscott Street
1109 ft · 23 sec · Tapscott Street
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6
Continue on Howard Avenue
1654 ft · 35 sec · Howard Avenue
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7
Turn right onto Eastern Parkway
1.1 km · 1 min · Eastern Parkway
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8
Turn right onto Dean Street
914 ft · 35 sec · Dean Street
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9
Turn slight left onto East New York Avenue
1808 ft · 46 sec · East New York Avenue
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10
Continue on Jamaica Avenue
854 ft · 19 sec · Jamaica Avenue
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11
Turn left onto Jackie Robinson Parkway
4.8 mi · 9 min · Jackie Robinson Parkway
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12
Take the exit slight right toward I 678 North: Van Wyck Expressway, Bronx
2351 ft · 1 min
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13
Merge slight left onto Van Wyck Expressway
3.8 mi · 6 min · Van Wyck Expressway
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14
Merge slight left onto Whitestone Expressway
2 mi · 3 min · Whitestone Expressway
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15
Continue on Bronx-Whitestone Bridge
1.3 mi · 2 min · Bronx-Whitestone Bridge
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16
Continue on Hutchinson River Expressway
1.2 mi · 2 min · Hutchinson River Expressway
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17
Continue on Hutchinson River Parkway
6.3 mi · 9 min · Hutchinson River Parkway
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18
Take the exit slight right
618 ft · 24 sec
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19
Turn left onto Lincoln Avenue
1.2 km · 1 min · Lincoln Avenue
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20
Turn right onto North Columbus Avenue
2040 ft · 43 sec · North Columbus Avenue
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21
Take the ramp left toward Cross County Parkway West
1512 ft · 38 sec
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22
Merge slight left onto Cross County Parkway
3011 ft · 54 sec · Cross County Parkway
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23
Take the exit slight right toward Bronx Parkway, Sprain Parkway
653 ft · 19 sec
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24
Keep slight right to continue on Bronx Parkway North, Sprain Parkway
1980 ft · 1 min
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25
Merge slight left onto Bronx River Parkway
1714 ft · 33 sec · Bronx River Parkway
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26
Keep slight left to continue on Sprain Brook Parkway
12.6 mi · 17 min · Sprain Brook Parkway
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27
Continue on Taconic State Parkway
1.8 mi · 2 min · Taconic State Parkway
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28
Take the exit slight right toward NY 9A, NY 100 North
2593 ft · 1 min
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29
Continue straight
2.4 mi · 4 min
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30
Turn left onto Chappaqua Road
144 m · 17 sec · Chappaqua Road
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31
Turn straight onto Pleasantville Road
1.3 km · 2 min · Pleasantville Road
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32
At the end of the road, turn left onto Croton Avenue
1702 ft · 51 sec · Croton Avenue
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33
Continue on Upper Croton Avenue
2158 ft · 1 min · Upper Croton Avenue
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34
Arrive at your destination
0 m · 1 sec · Upper Croton Avenue
Car Route Details
A richer read on the saved driving route between Sheepshead Bay and Ossining.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Sprain Brook Parkway
Keep slight left to continue on Sprain Brook Parkway
12.6 mi · 00h 17m
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.
Sunny leaving Sheepshead Bay and Sunny near Ossining.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Sheepshead Bay to Ossining?
The road trip is about 49 miles (78.9 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 24.5 miles from Sheepshead Bay and 24.5 miles from Ossining.
How much longer is the road route than the straight-line distance?
The direct path is about 39.7 miles (63.9 km), while the road route adds roughly 9.3 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 3:46 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $7.70 one way or $15.39 round trip. Estimated CO2 is about 15.4 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Sheepshead Bay and Sunny near Ossining.
Stop Ideas Near Eastchester
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Radio City Music Hall
City Hall Barber Shop
Orangetown Town Hall
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 Sheepshead Bay and Ossining. Straight-line distance: 39.74 mi (63.95 km).
#1 Sheepshead Bay
Sheepshead Bay is a place in New York, United States.
| Population | 0 |
| Coordinates | 40.5912200, -73.9445800 |
| Altitude | 3 |
| 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: 79 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 38m |
| 40 mph (64.37 km/h) | 01h 13m |
| 50 mph (80.47 km/h) | 00h 58m |
| 60 mph (96.56 km/h) | 00h 49m |
| 70 mph (112.65 km/h) | 00h 42m |
| 80 mph (129 km/h) | 00h 36m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.45 | $7.70 | $15.39 |
| Mid-grade | $4.98 | $8.62 | $17.24 |
| Premium | $5.38 | $9.31 | $18.62 |
| Diesel | $6.51 | $11.26 | $22.52 |
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 · Oct 15, 2026