How far is White Plains, NY from Southold, NY?
The driving distance from White Plains, NY to Southold, NY is about 103.6 miles (166.7 km), with a travel time of about 02h 34m by car.
- The straight-line flight distance is about 69.7 miles (112.1 km).
- For a round trip, plan for roughly 05h 08m 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 34m.
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.
Census-designated place in Suffolk County, New York
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 White Plains and Southold.
Turn-by-Turn Driving Directions
Step-by-step road directions between White Plains and Southold.
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1
Start on Main Street
22 m · 7 sec · Main Street
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2
Turn left onto North Broadway
142 m · 8 sec · North Broadway
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3
Turn slight left onto Hamilton Avenue
37 m · 5 sec · Hamilton Avenue
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4
Continue on North Broadway
2069 ft · 58 sec · North Broadway
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5
Turn left onto South Broadway
654 ft · 19 sec · South Broadway
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6
Turn right onto Maple Avenue
760 ft · 23 sec · Maple Avenue
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7
Turn left onto Mamaroneck Avenue
1216 ft · 30 sec · Mamaroneck Avenue
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8
Keep slight right to continue on Old Mamaroneck Road
1.8 mi · 3 min · Old Mamaroneck Road
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9
Continue on Secor Road
1540 ft · 31 sec · Secor Road
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10
Keep slight right to continue on New Rochelle, Mamaroneck, Larchmont
135 m · 9 sec
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11
Turn straight onto Heathcote Bypass
1 mi · 2 min · Heathcote Bypass
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12
Turn straight onto Weaver Street
2941 ft · 1 min · Weaver Street
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13
Turn right onto Stratton Road
1156 ft · 38 sec · Stratton Road
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14
Turn left onto Pinebrook Boulevard
159 m · 16 sec · Pinebrook Boulevard
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15
Take the ramp right toward Hutchinson Parkway South
1276 ft · 31 sec
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16
Merge slight left onto Hutchinson River Parkway
2.7 mi · 4 min · Hutchinson River Parkway
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17
Keep slight right to continue on Hutchinson River Parkway
5.9 mi · 9 min · Hutchinson River Parkway
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18
Take the exit slight right toward I 95 South: George Washington Bridge, Stillwell Avenue
43 m · 5 sec
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19
Keep slight right to continue on I 95 South: George Washington Bridge
1265 ft · 47 sec
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20
Merge slight left onto New England Thruway
1861 ft · 32 sec · New England Thruway
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21
Continue on Bruckner Expressway
1.3 mi · 2 min · Bruckner Expressway
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22
Keep slight left to continue on Throgs Neck Expressway
2.2 mi · 3 min · Throgs Neck Expressway
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23
Continue on Throgs Neck Bridge
2 mi · 3 min · Throgs Neck Bridge
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24
Continue on Clearview Expressway
3.2 mi · 3 min · Clearview Expressway
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25
Take the exit slight right toward I 495: Manhattan, Eastern Long Island
810 ft · 28 sec
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26
Keep slight left to continue on I 495 East: Long Island Expressway, Eastern Long Island
1448 ft · 39 sec
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27
Merge slight left onto Long Island Expressway
58.9 mi · 1 hr 20 min · Long Island Expressway
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28
Keep slight left to continue on CR 58 East: Old Country Road, Greenport, Orient
1.2 km · 1 min
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29
Keep slight left to continue on CR 58 east: Greenport, Orient
150 m · 14 sec
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30
Turn straight onto Old Country Road
2.3 mi · 5 min · Old Country Road
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31
Enter the roundabout and take exit 2 toward Old Country Road
33 m · 6 sec · Old Country Road
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32
Exit the roundabout onto Old Country Road
1.4 km · 2 min · Old Country Road
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33
Turn left onto Northville Turnpike
2.3 mi · 4 min · Northville Turnpike
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34
Turn right onto Sound Avenue
5.4 mi · 9 min · Sound Avenue
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35
Continue on Middle Road
8.8 mi · 13 min · Middle Road
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36
Take the exit right toward Southold
71 m · 13 sec
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37
Turn slight right onto Youngs Avenue
2820 ft · 1 min · Youngs Avenue
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38
Arrive at your destination
0 m · 1 sec · Youngs Avenue
Car Route Details
A richer read on the saved driving route between White Plains and Southold.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Long Island Expressway
Merge slight left onto Long Island Expressway
58.9 mi · 01h 20m
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 White Plains and Sunny near Southold.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from White Plains to Southold?
The road trip is about 103.6 miles (166.7 km) and usually takes 02h 34m 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?
Brentwood is a useful midpoint, sitting about 51.7 miles from White Plains and 51.9 miles from Southold.
How much longer is the road route than the straight-line distance?
The direct path is about 69.7 miles (112.1 km), while the road route adds roughly 33.9 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 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 1:22 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $16.24 one way or $32.47 round trip. Estimated CO2 is about 32.4 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around White Plains and Sunny near Southold.
Stop Ideas Near Brentwood
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Town of Babylon History Museum at Old Town Hall
Brookhaven Town Hall
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Brentwood.
Stamford Transportation Center
Bridgeport
New Rochelle station
Yonkers station
Flight Path Map
This map shows the direct air route between White Plains and Southold. Straight-line distance: 69.68 mi (112.14 km).
#1 White Plains
The most populous city in Westchester County, New York.
| Population | 58,286 |
| Coordinates | 41.0339900, -73.7629100 |
| Altitude | 65 |
| Country | United States |
#2 Southold
Town in New York
| Population | 22,282 |
| Coordinates | 41.0648200, -72.4262000 |
| Altitude | 7 |
| Country | United States |
End: Southold (-72.4262, 41.06482)
Estimated Travel Time
Distance: 167 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 27m |
| 40 mph (64.37 km/h) | 02h 35m |
| 50 mph (80.47 km/h) | 02h 04m |
| 60 mph (96.56 km/h) | 01h 43m |
| 70 mph (112.65 km/h) | 01h 28m |
| 80 mph (129 km/h) | 01h 17m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.45 | $16.24 | $32.47 |
| Mid-grade | $4.98 | $18.18 | $36.37 |
| Premium | $5.38 | $19.64 | $39.29 |
| Diesel | $6.51 | $23.76 | $47.52 |
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