How far is Ossining, NY from Sheepshead Bay, NY?
The driving distance from Ossining, NY to Sheepshead Bay, NY is about 51.8 miles (83.4 km), with a travel time of about 01h 27m by car.
- The straight-line flight distance is about 39.7 miles (63.9 km).
- For a round trip, plan for roughly 02h 54m 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 27m.
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.
Showers And Thunderstorms
Rain Showers
Driving Route Map
The map below follows the saved road route between Ossining and Sheepshead Bay.
Turn-by-Turn Driving Directions
Step-by-step road directions between Ossining and Sheepshead Bay.
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1
Start on Upper Croton Avenue
1558 ft · 50 sec · Upper Croton Avenue
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2
Continue on Upper Croton Avenue
600 ft · 17 sec · Upper Croton Avenue
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3
Continue on Croton Avenue
1702 ft · 53 sec · Croton Avenue
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4
Turn right onto Pleasantville Road
1.3 km · 2 min · Pleasantville Road
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5
Turn straight onto Chappaqua Road
133 m · 17 sec · Chappaqua Road
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6
Turn right
2.3 mi · 4 min
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7
Take the exit straight toward New York City
2442 ft · 59 sec
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8
Merge slight left onto Taconic State Parkway
1.9 mi · 3 min · Taconic State Parkway
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9
Keep slight left to continue on Sprain Brook Parkway
12.8 mi · 17 min · Sprain Brook Parkway
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10
Continue on Bronx River Parkway
2330 ft · 44 sec · Bronx River Parkway
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11
Take the exit slight right toward Cross County Parkway East, Mount Vernon
2217 ft · 1 min
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12
Merge slight left onto Cross County Parkway (local lanes)
1.2 mi · 2 min · Cross County Parkway (local lanes)
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13
Take the exit slight right toward Hutchinson Parkway South, Whitestone Bridge
3095 ft · 1 min
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14
Merge slight left onto Hutchinson River Parkway
6.6 mi · 10 min · Hutchinson River Parkway
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15
Continue on Hutchinson River Expressway
1.2 mi · 2 min · Hutchinson River Expressway
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16
Continue on Bronx-Whitestone Bridge
1.3 mi · 2 min · Bronx-Whitestone Bridge
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17
Continue on Whitestone Expressway
2.3 mi · 3 min · Whitestone Expressway
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18
Keep slight left to continue on Van Wyck Expressway
7.1 mi · 10 min · Van Wyck Expressway
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19
Take the exit slight right toward Belt Parkway West
859 ft · 21 sec
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20
Keep slight right to continue on Belt Parkway West, Verrazano Bridge
2610 ft · 1 min
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21
Merge slight left onto Belt Parkway
9.5 mi · 14 min · Belt Parkway
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22
Take the exit slight right toward Knapp Street, Sheepshead Bay
1053 ft · 26 sec
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23
Continue on Shore Parkway
1.3 km · 2 min · Shore Parkway
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24
Turn right onto Bedford Avenue
2159 ft · 1 min · Bedford Avenue
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25
Turn right onto Avenue Y
34 m · 5 sec · Avenue Y
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26
Arrive at your destination
0 m · 1 sec · Avenue Y
Car Route Details
A richer read on the saved driving route between Ossining and Sheepshead Bay.
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
12.8 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.
Showers And Thunderstorms leaving Ossining and Rain Showers near Sheepshead Bay.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Ossining to Sheepshead Bay?
The road trip is about 51.8 miles (83.4 km) and usually takes 01h 27m 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 25.8 miles from Ossining and 26 miles from Sheepshead Bay.
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 12.1 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 3:36 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $8.14 one way or $16.28 round trip. Estimated CO2 is about 16.3 kg one way.
What should you check before leaving?
Before you leave, expect Showers And Thunderstorms around Ossining and Rain Showers near Sheepshead Bay.
Stop Ideas Near Eastchester
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Radio City Music Hall
The Yard: City Hall Park NYC
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 Ossining and Sheepshead Bay. Straight-line distance: 39.74 mi (63.95 km).
#1 Ossining
Town in Westchester County, New York, United States
| Population | 37,551 |
| Coordinates | 41.1628700, -73.8615200 |
| Altitude | 49 |
| Country | United States |
#2 Sheepshead Bay
Sheepshead Bay is a place in New York, United States.
| Population | 0 |
| Coordinates | 40.5912200, -73.9445800 |
| Altitude | 3 |
| Country | United States |
End: Avenue Y (-73.944577, 40.591203)
Estimated Travel Time
Distance: 83 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 43m |
| 40 mph (64.37 km/h) | 01h 17m |
| 50 mph (80.47 km/h) | 01h 02m |
| 60 mph (96.56 km/h) | 00h 51m |
| 70 mph (112.65 km/h) | 00h 44m |
| 80 mph (129 km/h) | 00h 38m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.45 | $8.14 | $16.28 |
| Mid-grade | $4.98 | $9.12 | $18.23 |
| Premium | $5.38 | $9.85 | $19.70 |
| Diesel | $6.51 | $11.91 | $23.82 |
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