How far is Pleasantville, NY from Oyster Bay, NY?
The driving distance from Pleasantville, NY to Oyster Bay, NY is about 445.5 miles (717 km), with a travel time of about 07h 13m by car.
- The straight-line flight distance is about 319.6 miles (514.4 km).
- For a round trip, plan for roughly 14h 26m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 7:30 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 07h 13m.
Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
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.
Human settlement in Chemung County, New York, United States of America
Route Weather Snapshot
Check the forecast at both ends before you head out.
Chance Rain Showers then Chance Rain And Snow Showers
Rain Showers Likely
Driving Route Map
The map below follows the saved road route between Pleasantville and Oyster Bay.
Turn-by-Turn Driving Directions
Step-by-step road directions between Pleasantville and Oyster Bay.
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1
Start on Centralia-Hartfield Road
1.7 mi · 4 min · Centralia-Hartfield Road
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2
Turn right onto Bayview Road
6.7 mi · 11 min · Bayview Road
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3
At the end of the road, turn right onto Bemus-Ellery Road
142 m · 13 sec · Bemus-Ellery Road
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4
Continue on Center Street
545 ft · 16 sec · Center Street
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5
Turn left
1.3 km · 2 min
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6
Take the ramp straight toward Jamestown
2771 ft · 56 sec
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7
Merge slight right onto Southern Tier Expressway
7 mi · 8 min · Southern Tier Expressway
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8
Take the exit slight right toward NY 60: Jamestown
1241 ft · 30 sec
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9
Turn right onto North Main Street
732 ft · 20 sec · North Main Street
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10
Turn left onto Marvin Parkway
1121 ft · 30 sec · Marvin Parkway
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11
Turn right onto Lakeview Avenue
1.2 km · 2 min · Lakeview Avenue
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12
Turn left onto Newton Avenue
22 m · 2 sec · Newton Avenue
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13
Turn right onto Winsor Street
1.4 km · 2 min · Winsor Street
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14
Continue straight
902 ft · 28 sec
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15
Turn slight right onto Allen Street
1017 ft · 27 sec · Allen Street
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16
Continue on Maple Street
2016 ft · 49 sec · Maple Street
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17
Continue on West Virginia Boulevard
1869 ft · 53 sec · West Virginia Boulevard
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18
Turn right onto Glenview Avenue
779 ft · 27 sec · Glenview Avenue
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19
Turn left onto Martin Road
2.1 mi · 4 min · Martin Road
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20
At the end of the road, turn left onto Foote Avenue
978 ft · 18 sec · Foote Avenue
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21
Turn right
15.6 mi · 19 min
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22
Turn right onto West 4th Avenue
1071 ft · 23 sec · West 4th Avenue
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23
Turn left onto Hickory Street
956 ft · 23 sec · Hickory Street
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24
Continue on Hickory Bridge
746 ft · 24 sec · Hickory Bridge
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25
Turn left onto Crescent Park
2270 ft · 58 sec · Crescent Park
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26
Turn left onto Crescent Park
1.8 mi · 4 min · Crescent Park
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27
Continue on Main Street
1169 ft · 35 sec · Main Street
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28
Continue on Grand Army of the Republic Highway
2.9 mi · 5 min · Grand Army of the Republic Highway
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29
Continue on North Main Street
1.4 mi · 3 min · North Main Street
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30
Continue on Grand Army of the Republic Highway
4.5 mi · 6 min · Grand Army of the Republic Highway
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31
Continue on West Main Street
1.1 mi · 2 min · West Main Street
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32
Take the exit slight right toward PA 666 West
81 m · 9 sec
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33
Merge slight left onto South Main Street
2.3 mi · 4 min · South Main Street
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34
Continue straight
8.5 mi · 12 min
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35
At the end of the road, turn left
2.9 mi · 4 min
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36
Turn right
15.2 mi · 23 min
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37
Turn left onto West Main Street
1 mi · 3 min · West Main Street
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38
Continue on Boot Jack Road
11.2 mi · 16 min · Boot Jack Road
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39
Turn left onto Penfield Road
3.7 mi · 6 min · Penfield Road
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40
Continue on Hoovertown Road
5 mi · 9 min · Hoovertown Road
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41
Continue on State Park Road
8.1 mi · 14 min · State Park Road
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42
Turn left
1681 ft · 41 sec
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43
Merge slight left onto Keystone Shortway
262.7 mi · 4 hr 58 min · Keystone Shortway
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44
Keep slight right to continue on Christopher Columbus Highway
5.5 mi · 6 min · Christopher Columbus Highway
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45
Keep slight left to continue on I 95 North: George Washington Bridge, New York City
1503 ft · 23 sec
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46
Keep slight right to continue on Leonia, Teaneck
2128 ft · 38 sec
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47
Turn right onto Leonia
1032 ft · 35 sec
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48
Turn straight onto Degraw Avenue
138 m · 9 sec · Degraw Avenue
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49
Continue on Fort Lee Road
1.1 mi · 2 min · Fort Lee Road
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50
Continue on Main Street
143 m · 13 sec · Main Street
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51
Take the ramp left toward George Washington Bridge
144 m · 13 sec
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52
Merge slight left onto Bergen Boulevard
1552 ft · 29 sec · Bergen Boulevard
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53
Take the exit slight left toward George Washington Bridge Upper Level
95 m · 5 sec
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54
Merge slight left
1649 ft · 20 sec
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55
Keep slight left
1.3 km · 1 min
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56
Continue on George Washington Bridge (upper level)
3174 ft · 1 min · George Washington Bridge (upper level)
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57
Continue on Trans-Manhattan Expressway
1.2 km · 1 min · Trans-Manhattan Expressway
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58
Continue on Cross Bronx Expressway
4.7 mi · 6 min · Cross Bronx Expressway
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59
Keep slight right to continue on Cross Bronx Expressway
2 mi · 3 min · Cross Bronx Expressway
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60
Merge slight left onto Throgs Neck Expressway
3271 ft · 58 sec · Throgs Neck Expressway
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61
Continue on Throgs Neck Bridge
2 mi · 3 min · Throgs Neck Bridge
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62
Continue on Clearview Expressway
2 mi · 2 min · Clearview Expressway
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63
Take the exit slight right toward NY 25A: Northern Boulevard
1133 ft · 32 sec
-
64
Continue on Clearview Expressway
139 m · 18 sec · Clearview Expressway
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65
Turn left onto Northern Boulevard
14.5 mi · 25 min · Northern Boulevard
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66
Turn left onto Jericho Oyster Bay Road
1358 ft · 30 sec · Jericho Oyster Bay Road
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67
Turn straight onto Oyster Bay Road
2534 ft · 47 sec · Oyster Bay Road
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68
Keep slight left to continue on Oyster Bay Road
79 m · 4 sec · Oyster Bay Road
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69
Continue on Pine Hollow Road
1.4 km · 1 min · Pine Hollow Road
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70
Continue on South Street
32 m · 6 sec · South Street
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71
Turn right onto Berry Hill Road
34 m · 9 sec · Berry Hill Road
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72
Continue on Berry Hill Road
19 m · 3 sec · Berry Hill Road
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73
Arrive at your destination
0 m · 1 sec · Berry Hill Road
Car Route Details
A richer read on the saved driving route between Pleasantville and Oyster Bay.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
Keystone Shortway
Merge slight left onto Keystone Shortway
263 mi · 04h 58m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
Better with a longer stop
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
Chance Rain Showers then Chance Rain And Snow Showers leaving Pleasantville and Rain Showers Likely near Oyster Bay.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Pleasantville to Oyster Bay?
The road trip is about 445.5 miles (717 km) and usually takes 07h 13m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
What is the halfway point on this route?
Wellsburg is a useful midpoint, sitting about 205.1 miles from Pleasantville and 240.5 miles from Oyster Bay.
How much longer is the road route than the straight-line distance?
The direct path is about 319.6 miles (514.4 km), while the road route adds roughly 125.9 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 7:30 AM EDT. Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $63.02 one way or $126.04 round trip. Estimated CO2 is about 139.7 kg one way.
What should you check before leaving?
Before you leave, expect Chance Rain Showers then Chance Rain And Snow Showers around Pleasantville and Rain Showers Likely near Oyster Bay.
Stop Ideas Near Wellsburg
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 Wellsburg.
Scranton, PA
Wilkes-Barre, PA
Flight Path Map
This map shows the direct air route between Pleasantville and Oyster Bay. Straight-line distance: 319.62 mi (514.38 km).
#1 Pleasantville
Village in Westchester County, New York, United States
| Population | 7,227 |
| Coordinates | 42.2608900, -79.4283800 |
| Altitude | 429 |
| 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: 717 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 14h 50m |
| 40 mph (64.37 km/h) | 11h 08m |
| 50 mph (80.47 km/h) | 08h 54m |
| 60 mph (96.56 km/h) | 07h 25m |
| 70 mph (112.65 km/h) | 06h 21m |
| 80 mph (129 km/h) | 05h 33m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.01 | $63.02 | $126.04 |
| Mid-grade | $4.48 | $70.44 | $140.88 |
| Premium | $4.86 | $76.41 | $152.83 |
| Diesel | $4.69 | $73.79 | $147.58 |
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 19, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.