How far is Southold, NY from Smithtown, NY?
The driving distance from Southold, NY to Smithtown, NY is about 53.2 miles (85.6 km), with a travel time of about 01h 10m by car.
- The straight-line flight distance is about 42.9 miles (69.1 km).
- For a round trip, plan for roughly 02h 20m 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 10m.
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
Driving Route Map
The map below follows the saved road route between Southold and Smithtown.
Turn-by-Turn Driving Directions
Step-by-step road directions between Southold and Smithtown.
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1
Start on Youngs Avenue
2961 ft · 1 min · Youngs Avenue
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2
Turn left onto Middle Road
8.9 mi · 13 min · Middle Road
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3
Continue on Sound Avenue
14.9 mi · 25 min · Sound Avenue
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4
At the end of the road, turn right onto NY-25A
1.3 mi · 2 min · NY-25A
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5
Continue on Route 25A
1.5 mi · 3 min · Route 25A
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6
Continue on Main Street
1.5 mi · 3 min · Main Street
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7
Turn straight onto Rocky Point Bypass
1.5 mi · 2 min · Rocky Point Bypass
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8
Continue on Main Street
5.3 mi · 9 min · Main Street
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9
Turn straight onto Nesconset Highway
6.9 mi · 10 min · Nesconset Highway
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10
Continue on Smithtown Bypass
3194 ft · 52 sec · Smithtown Bypass
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11
Take the exit slight right toward Route 25, Middle Country Road WEST, Smithtown
648 ft · 10 sec
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12
Turn slight right onto Middle Country Road
1.9 mi · 3 min · Middle Country Road
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13
Continue on East Main Street
1.3 mi · 2 min · East Main Street
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14
Arrive at your destination
0 m · 1 sec · West Main Street
Car Route Details
A richer read on the saved driving route between Southold and Smithtown.
Straightforward drive
The saved road route has a manageable number of maneuvers and should be easy to follow with normal attention to signs.
Sound Avenue
Continue on Sound Avenue
14.9 mi · 00h 25m
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 Southold and Sunny near Smithtown.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Southold to Smithtown?
The road trip is about 53.2 miles (85.6 km) and usually takes 01h 10m 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?
Wading River is a useful midpoint, sitting about 23.1 miles from Southold and 30.1 miles from Smithtown.
How much longer is the road route than the straight-line distance?
The direct path is about 42.9 miles (69.1 km), while the road route adds roughly 10.3 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 4:10 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $8.36 one way or $16.72 round trip. Estimated CO2 is about 16.7 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Southold and Sunny near Smithtown.
Stop Ideas Near Wading River
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 Wading River.
Bridgeport
Union Station
Old Saybrook station
Wallingford station
Flight Path Map
This map shows the direct air route between Southold and Smithtown. Straight-line distance: 42.91 mi (69.06 km).
#1 Southold
Town in New York
| Population | 22,282 |
| Coordinates | 41.0648200, -72.4262000 |
| Altitude | 7 |
| Country | United States |
#2 Smithtown
Census-designated place in Suffolk County, New York
| Population | 110,876 |
| Coordinates | 40.8559300, -73.2006700 |
| Altitude | 18 |
| Country | United States |
End: West Main Street (-73.200729, 40.855811)
Estimated Travel Time
Distance: 86 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 46m |
| 40 mph (64.37 km/h) | 01h 19m |
| 50 mph (80.47 km/h) | 01h 03m |
| 60 mph (96.56 km/h) | 00h 53m |
| 70 mph (112.65 km/h) | 00h 45m |
| 80 mph (129 km/h) | 00h 39m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.45 | $8.36 | $16.72 |
| Mid-grade | $4.98 | $9.37 | $18.73 |
| Premium | $5.38 | $10.12 | $20.24 |
| Diesel | $6.51 | $12.24 | $24.47 |
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