How far is Smithtown, NY from New Windsor, NY?
The driving distance from Smithtown, NY to New Windsor, NY is about 100.8 miles (162.3 km), with a travel time of about 02h 18m by car.
- The straight-line flight distance is about 60.6 miles (97.5 km).
- For a round trip, plan for roughly 04h 37m 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 02h 18m.
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.
City in New York County, New York, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Sunny
Driving Route Map
The map below follows the saved road route between Smithtown and New Windsor.
Turn-by-Turn Driving Directions
Step-by-step road directions between Smithtown and New Windsor.
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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
-
20
Keep slight left to continue on Trans-Manhattan Expressway
1.1 km · 1 min · Trans-Manhattan Expressway
-
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 right to continue on Palisades Interstate Parkway
37.4 mi · 48 min · Palisades Interstate Parkway
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24
Enter the roundabout and take exit 3 toward the route
528 ft · 8 sec
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25
Exit the rotary
14.6 mi · 21 min
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26
Turn left onto Union Avenue
1922 ft · 57 sec · Union Avenue
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27
Arrive at your destination
0 m · 1 sec · Union Avenue
Car Route Details
A richer read on the saved driving route between Smithtown and New Windsor.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Palisades Interstate Parkway
Keep slight right to continue on Palisades Interstate Parkway
37.4 mi · 00h 48m
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 Smithtown and Sunny near New Windsor.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Smithtown to New Windsor?
The road trip is about 100.8 miles (162.3 km) and usually takes 02h 18m 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?
Inwood is a useful midpoint, sitting about 50.4 miles from Smithtown and 50.5 miles from New Windsor.
How much longer is the road route than the straight-line distance?
The direct path is about 60.6 miles (97.5 km), while the road route adds roughly 40.2 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 1:52 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $15.83 one way or $31.67 round trip. Estimated CO2 is about 31.6 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Smithtown and Sunny near New Windsor.
Stop Ideas Near Inwood
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
City Hall Parking Lot
The Yard: City Hall Park NYC
CITY HALL LOBBY
Diamond City Hall Photography
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Inwood.
Yonkers station
New Rochelle station
Pennsylvania Station
Pennsylvania Station
Flight Path Map
This map shows the direct air route between Smithtown and New Windsor. Straight-line distance: 60.6 mi (97.53 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 New Windsor
Town in Carroll County, Maryland, United States
| Population | 27,475 |
| Coordinates | 41.4767600, -74.0237500 |
| Altitude | 49 |
| Country | United States |
End: New Windsor (-74.02375, 41.47676)
Estimated Travel Time
Distance: 162 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 21m |
| 40 mph (64.37 km/h) | 02h 31m |
| 50 mph (80.47 km/h) | 02h 00m |
| 60 mph (96.56 km/h) | 01h 40m |
| 70 mph (112.65 km/h) | 01h 26m |
| 80 mph (129 km/h) | 01h 15m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.45 | $15.83 | $31.67 |
| Mid-grade | $4.98 | $17.74 | $35.47 |
| Premium | $5.38 | $19.16 | $38.32 |
| Diesel | $6.51 | $23.17 | $46.34 |
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