How far is Smithtown, NY from Pleasantville, NY?
The driving distance from Smithtown, NY to Pleasantville, NY is about 430.6 miles (693 km), with a travel time of about 09h 13m by car.
- The straight-line flight distance is about 336.2 miles (541.1 km).
- For a round trip, plan for roughly 18h 27m 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 09h 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.
Partly Sunny
Driving Route Map
The map below follows the saved road route between Smithtown and Pleasantville.
Turn-by-Turn Driving Directions
Step-by-step road directions between Smithtown and Pleasantville.
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1
Start on West Main Street
2964 ft · 52 sec · West Main Street
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2
Keep slight left to continue on West Main Street
55 m · 5 sec · West Main Street
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3
Continue on Jericho Turnpike
4 mi · 6 min · Jericho Turnpike
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4
Take the ramp slight right toward SM South: Bay Shore
1110 ft · 27 sec
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5
Merge slight left onto Sunken Meadow State Parkway
1.9 mi · 2 min · Sunken Meadow State Parkway
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6
Continue on Sagtikos State Parkway
1.2 km · 50 sec · Sagtikos State Parkway
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7
Take the exit slight right toward I 495 West: New York
688 ft · 17 sec
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8
Keep slight left to continue on I 495 West: New York
955 ft · 23 sec
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9
Turn straight onto LIE North Service Road
1987 ft · 34 sec · LIE North Service Road
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10
Turn straight onto North Service Road
770 ft · 14 sec · North Service Road
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11
Take the ramp slight left toward I 495 West: New York
879 ft · 22 sec
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12
Merge slight left onto Long Island Expressway
24.8 mi · 34 min · Long Island Expressway
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13
Take the exit slight right toward Cross Island Parkway, Whitestone Bridge, Kennedy Airport
1267 ft · 27 sec
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14
Keep slight right to continue on Cross Island Parkway North, Whitestone Bridge
1604 ft · 38 sec
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15
Merge slight left onto Cross Island Parkway
3.1 mi · 5 min · Cross Island Parkway
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16
Take the exit slight right toward I 295 North: Throgs Neck Bridge, Bronx, New England
2905 ft · 1 min
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17
Merge slight left onto Throgs Neck Bridge
1.8 mi · 3 min · Throgs Neck Bridge
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18
Continue on Throgs Neck Expressway
1.1 km · 1 min · Throgs Neck Expressway
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19
Keep slight left to continue on Cross Bronx Expressway
6.6 mi · 9 min · Cross Bronx Expressway
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20
Keep slight left to continue on Trans-Manhattan Expressway
1.1 km · 1 min · Trans-Manhattan Expressway
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21
Continue on George Washington Bridge (upper level)
3167 ft · 60 sec · George Washington Bridge (upper level)
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22
Continue straight
2659 ft · 48 sec
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23
Keep slight left
3214 ft · 39 sec
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24
Keep slight left
559 ft · 9 sec
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25
Take the exit slight right toward I 95 South, NJTP South: Hackensack
1270 ft · 23 sec
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26
Keep slight left to continue on I 95 South, NJTP South: Hackensack
1884 ft · 29 sec
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27
Merge slight left onto New Jersey Turnpike
2 mi · 3 min · New Jersey Turnpike
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28
Take the exit slight right toward I 80 West: Paterson, Hackensack
1.3 km · 1 min
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29
Continue on Christopher Columbus Highway
68.2 mi · 1 hr 21 min · Christopher Columbus Highway
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30
Keep slight left to continue on Keystone Shortway
5.5 mi · 8 min · Keystone Shortway
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31
Keep slight left to continue on Keystone Shortway
194.5 mi · 3 hr 36 min · Keystone Shortway
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32
Take the exit slight right toward PA 153: Clearfield, Penfield
2880 ft · 1 min
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33
Keep slight right
1315 ft · 32 sec
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34
Turn straight onto State Park Road
7.5 mi · 13 min · State Park Road
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35
Continue on Hoovertown Road
5 mi · 9 min · Hoovertown Road
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36
Continue on Penfield Road
3.7 mi · 6 min · Penfield Road
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37
At the end of the road, turn right
12.3 mi · 19 min
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38
Turn right onto Montmorenci Avenue
1.6 km · 2 min · Montmorenci Avenue
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39
Continue on Montmorenci Road
8.8 mi · 13 min · Montmorenci Road
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40
Continue on Highland Road
5.4 mi · 8 min · Highland Road
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41
At the end of the road, turn left onto Kane-Russell City Road
2.7 mi · 4 min · Kane-Russell City Road
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42
Take the exit slight right
8.6 mi · 12 min
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43
Continue straight
2.3 mi · 5 min
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44
At the end of the road, turn left onto West Main Street
1.2 mi · 2 min · West Main Street
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45
Continue on Grand Army of the Republic Highway
4.5 mi · 6 min · Grand Army of the Republic Highway
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46
Continue on South Main Street
1.4 mi · 3 min · South Main Street
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47
Continue on Grand Army of the Republic Highway
2.9 mi · 5 min · Grand Army of the Republic Highway
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48
Continue on Main Street
1169 ft · 35 sec · Main Street
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49
Continue on Crescent Park
1.8 mi · 4 min · Crescent Park
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50
Continue on Crescent Park
2270 ft · 1 min · Crescent Park
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51
Turn right onto Hickory Bridge
746 ft · 17 sec · Hickory Bridge
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52
Continue on Hickory Street
956 ft · 25 sec · Hickory Street
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53
Turn right onto West 4th Avenue
1071 ft · 23 sec · West 4th Avenue
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54
Turn left onto Market Street
15.6 mi · 19 min · Market Street
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55
At the end of the road, turn left onto Foote Avenue
978 ft · 16 sec · Foote Avenue
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56
Turn right onto Martin Road
2.1 mi · 4 min · Martin Road
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57
Turn right onto Glenview Avenue
779 ft · 23 sec · Glenview Avenue
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58
Turn left onto West Virginia Boulevard
1869 ft · 53 sec · West Virginia Boulevard
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59
Continue on Maple Street
2016 ft · 51 sec · Maple Street
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60
Continue on Allen Street
1075 ft · 29 sec · Allen Street
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61
Turn left onto Winsor Street
49 m · 5 sec · Winsor Street
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62
Continue straight
730 ft · 23 sec
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63
Continue on Winsor Street Bridge
1.4 km · 2 min · Winsor Street Bridge
-
64
At the end of the road, turn left onto Newton Avenue
22 m · 6 sec · Newton Avenue
-
65
Turn right onto Lakeview Avenue
1.2 km · 2 min · Lakeview Avenue
-
66
Turn left onto Marvin Parkway
1092 ft · 29 sec · Marvin Parkway
-
67
Turn right onto North Main Street
86 m · 6 sec · North Main Street
-
68
Keep slight left to continue on North Main Street
1075 ft · 22 sec · North Main Street
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69
Keep slight right to continue on North Main Street
2444 ft · 57 sec · North Main Street
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70
Merge slight left onto Southern Tier Expressway
7.1 mi · 8 min · Southern Tier Expressway
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71
Take the exit slight right toward Bemus Point
1.3 mi · 2 min
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72
Turn slight right onto Bemus Point, Ellery Center
1031 ft · 23 sec
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73
Turn right onto Bemus-Ellery Road
142 m · 18 sec · Bemus-Ellery Road
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74
Turn left onto Bayview Road
5.1 mi · 8 min · Bayview Road
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75
Keep slight right to continue on Bayview Road
1.6 mi · 3 min · Bayview Road
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76
Turn left onto Centralia-Hartfield Road
1.7 mi · 4 min · Centralia-Hartfield Road
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77
Arrive at your destination
0 m · 1 sec · Centralia-Hartfield Road
Car Route Details
A richer read on the saved driving route between Smithtown and Pleasantville.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
Keystone Shortway
Keep slight left to continue on Keystone Shortway
195 mi · 03h 36m
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.
Sunny leaving Smithtown and Partly Sunny near Pleasantville.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Smithtown to Pleasantville?
The road trip is about 430.6 miles (693 km) and usually takes 09h 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?
Chemung is a useful midpoint, sitting about 213.9 miles from Smithtown and 216.6 miles from Pleasantville.
How much longer is the road route than the straight-line distance?
The direct path is about 336.2 miles (541.1 km), while the road route adds roughly 94.4 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 $67.61 one way or $135.22 round trip. Estimated CO2 is about 135.1 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Smithtown and Partly Sunny near Pleasantville.
Stop Ideas Near Chemung
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 Chemung.
Scranton, PA
Wilkes-Barre, PA
Flight Path Map
This map shows the direct air route between Smithtown and Pleasantville. Straight-line distance: 336.2 mi (541.06 km).
#1 Smithtown
Census-designated place in Suffolk County, New York
| Population | 110,876 |
| Coordinates | 40.8559300, -73.2006700 |
| Altitude | 18 |
| Country | United States |
#2 Pleasantville
Village in Westchester County, New York, United States
| Population | 7,227 |
| Coordinates | 42.2608900, -79.4283800 |
| Altitude | 429 |
| Country | United States |
End: Pleasantville (-79.42838, 42.26089)
Estimated Travel Time
Distance: 693 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 14h 20m |
| 40 mph (64.37 km/h) | 10h 45m |
| 50 mph (80.47 km/h) | 08h 36m |
| 60 mph (96.56 km/h) | 07h 10m |
| 70 mph (112.65 km/h) | 06h 09m |
| 80 mph (129 km/h) | 05h 22m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.45 | $67.61 | $135.22 |
| Mid-grade | $4.98 | $75.73 | $151.45 |
| Premium | $5.38 | $81.81 | $163.61 |
| Diesel | $6.51 | $98.94 | $197.87 |
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