The drive from Southampton, NY to Oyster Bay, NY covers 67.1 miles and takes about 1h 37m behind the wheel.
This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Long Island Expressway, Sunrise Highway, County Road 39 for much of the mileage,
and the overall profile is mixed drive.
The longest uninterrupted segment is about 27.6 miles on Long Island Expressway.
At current regular gas prices, budget about $11.05 one way before food or hotel costs.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
33.6 miles from Southampton, NY
A natural place for your longest stop of the day
, about 49m into the drive
.
Oyster Bay is one of three towns in Nassau County, on Long Island, New York.
The town of Oyster Bay comprises a large portion of eastern Nassau County and includes a slew of villages and other communities. This article covers North Oyster Bay – the area closest to Oyster Bay itself (in other words, everything that is north of the Long Island Expressway). See South Oyster Bay for the southern half of the town (in other words, the area south of the expressway). See the article for Glen Cove for communities in the northwest part of the town that are closest to that city.
Doable as a same-day drive at 1h 37m. Total distance: 67.1 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 37m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (41%). Some complex stretches to watch for.
Drive Character
The drive from Southampton, NY to Oyster Bay, NY covers 67.1 miles and takes about 1h 37m, using a mix of highways and local roads.
Expect a mix of faster highway mileage and slower local approaches near the beginning or end.
There are about 19 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Long Island Expressway is the longest continuous segment at about 27.6 miles.
Elevation Profile
Mostly flat terrain
192 ft16 ft
Total Climb
273 ft
Total Descent
254 ft
Highest Point
192 ft
~62.3 mi in
Elevation Range
176 ft
How Hard Is This Drive?
This route mixes highway mileage with some local-road sections near the start or finish. You will hit about 10 points where you need to pay attention to lane position or signs. The trickiest moment comes around 1 miles in near NY 27; CR 39 / County Road 39.
Driving Effort5/10
Moderate - straightforward overall, but long enough or busy enough to require pacing
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 67.1 miles you will encounter 10 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
Where does it get tricky?
The main spots that need attention: at 1 miles (NY 27; CR 39 / County Road 39): Lane positioning matters here; at 29.2 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 29.5 miles (CR 16 / Horseblock Road): Lane positioning matters here.
Critical Maneuvers
5 of 10 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
5
1 mi into trip|~2m in|NY 27; CR 39 / County Road 39
Turn left onto NY 27; CR 39 / County Road 39
Lane positioning matters here
Use the left lane.
8
29.2 mi into trip|~42m in
Take the exit toward CR 16 West: Yaphank, Horseblock Road
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the right lane.
Exit 57N
Toward CR 16 West: Yaphank, Horseblock Road
5
29.5 mi into trip|~43m in|CR 16 / Horseblock Road
Turn right onto CR 16 / Horseblock Road
Lane positioning matters here
Use the left lane.
8
61.3 mi into trip|~1h 26m in
Take the exit toward South Oyster Bay Road, Bethpage, Syosset
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 43
Toward South Oyster Bay Road, Bethpage, Syosset
6
61.6 mi into trip|~1h 26m in|South Oyster Bay Road
Turn right onto South Oyster Bay Road
Lane positioning matters here
Use the left lane.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Southampton, NY and Oyster Bay, NY, road signs point toward Cr 16 West: Yaphank, Bethpage and Syosset.
Cr 16 West: Yaphank
29.2 mi in|~42m
Bethpage
61.3 mi in|~1h 26m
Syosset
61.3 mi in|~1h 26m
Main Roads
Road
Distance
Duration
Long Island Expressway
27.6 mi
36m
Sunrise Highway
24.2 mi
31m
County Road 39
4 mi
8m
Horseblock Road
3.9 mi
5m
Berry Hill Road
3.7 mi
6m
Jackson Avenue
1 mi
2m
South Oyster Bay Road
0.8 mi
1m
North Sea Road
0.7 mi
1m
Longest stretch:
Long Island Expressway
— 27.6 mi, about 36m
Turn-by-Turn Driving Directions
Step-by-step road directions between Southampton, NY and Oyster Bay, NY.
1
Start on Main Street
0.3 mi·1 min·Main Street
Use the straight lane.
2
Continue on North Sea Road
0.7 mi·1 min·North Sea Road
Use the straight / left lanes.
3
Turn left onto NY 27; CR 39
4.0 mi·8 min·County Road 39
Use the left lane.
4
Continue on NY 27
24 mi·31 min·Sunrise Highway
5
Take the exit
0.1 mi·23 sec
Exit 57NToward CR 16 West: Yaphank, Horseblock RoadUse the right lane.
6
Turn left onto CR 56
0.2 mi·21 sec·Victory Avenue
7
Turn right onto CR 16
3.9 mi·5 min·Horseblock Road
Use the left lane.
8
Turn left onto Express Drive North
0.2 mi·14 sec·Express Drive North
Use the left lane.
9
Take the ramp
0.2 mi·21 sec
Toward I 495 WEST: New York
10
Merge onto I 495
28 mi·36 min·Long Island Expressway
Use the straight / slight right lanes.
11
Take the exit
0.2 mi·32 sec
Exit 43Toward South Oyster Bay Road, Bethpage, SyossetUse the slight right lane.
12
Turn straight onto North Service Road
239 ft·11 sec·North Service Road
13
Turn right onto South Oyster Bay Road
0.8 mi·1 min·South Oyster Bay Road
Use the left lane.
14
Continue on Jackson Avenue
1.0 mi·2 min·Jackson Avenue
15
Turn slight left onto Berry Hill Road
283 ft·7 sec·Berry Hill Road
Use the left lane.
16
Continue on Berry Hill Road
2.4 mi·4 min·Berry Hill Road
17
Continue on Berry Hill Road
1.2 mi·2 min·Berry Hill Road
18
Continue on Berry Hill Road
64 ft·2 sec·Berry Hill Road
19
Arrive at destination
Berry Hill Road
Trip Plan
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 33.6 miles from Southampton, NY, or about 49m into the drive.
The longest continuous stretch on this route runs about 27.6 miles.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 67.1 miles or 1h 37m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 33.6 miles or 49m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 20m
Traffic, exits, and arrival timing usually matter more near Oyster Bay, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Southampton, NY so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Southampton, NY
This is one driving day of about 67.1 miles and 1h 37m.
Your first comfortable stop window is around 80 miles from Southampton, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
You may only need one short stretch stop if conditions stay smooth.
The longest stretch is on Long Island Expressway for about 27.6 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 33.6 mi from Southampton, NY
· 49m into the drive
The midpoint is around 33.6 miles from Southampton, NY, which is a good place for a longer meal and fuel stop.
Arriving in Oyster Bay, NY
The final approach into Oyster Bay, NY usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Oyster Bay, NY.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
National Parks Near This Route
Worth a detour if your schedule allows.
Fire Island National Seashore
National Seashore
Immerse yourself in an enchanting collage of coastal life and history. Rhythmic waves, high dunes, ancient maritime forests, historic landmarks and glimpses of wildlife, Fire Island has been a special...
8 mi from route
~21 min detour
Free
near mile 30.1
Park Closure: Pet Restrictions, Beach Driving Closures in Effect March 15 through Labor Day
Caution: Avian Influenza (HPAI) Suspected in Dead Birds in Seashore Areas
Merchant’s clerk, Revolutionary War soldier, first Secretary Treasury of the United States: Alexander Hamilton’s life is memorialized at The Grange, the home he built on a country estate in uptown Man...
22 mi from route
~55 min detour
Free
near mile 67.1
The final resting place of President Ulysses S. Grant and his wife, Julia, is the largest mausoleum in North America. It testifies to a people’s gratitude for the man who ended the bloodiest conflict...
23 mi from route
~57 min detour
Free
near mile 67.1
Before the 1960s, almost everything about living authentically as a lesbian, a bisexual person or a gay man was illegal. The Stonewall Uprising on June 28, 1969 is a milestone in the quest for civil r...
26 mi from route
~65 min detour
Free
near mile 67.1
The African Burial Ground stands as the oldest and largest known excavated burial site in North America for both free and enslaved Africans. It offers a profound testament to the enduring legacy of Af...
27 mi from route
~67 min detour
Free
near mile 67.1
Here at Federal Hall, George Washington took the oath of office as the first President of the United States, marking the beginning of the American constitutional republic. This historic site served as...
27 mi from route
~68 min detour
Free
near mile 67.1
Park data from the National Park Service API. Alerts update every 2 hours.
Fuel & Cost
Regular Gas
$11.05 one way
$22.09 round trip
$4.18/gal25.4 MPG avg24 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$11.94
$23.89
premium
$4.92
$13.01
$26.01
diesel
$5.61
$14.81
$29.63
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$11
Meals
$25–$50
Total
$36–$61
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 23.5 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $7 in charging
· 0 stops
· 65% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
20.1
0
$7.05
$3.22
Efficient EV
16.8
0
$5.87
$2.68
EV Truck/SUV
26.8
0
$9.39
$4.29
Gas CO2
23 kg
EV CO2
8 kg (65% less)
This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive.
Forecast as of Apr 15, 2026
Origin
Southampton, NY
Morning
in Southampton on Saturday
Local time
10:45 AM
EDT
Current temp
42°F
Unavailable
Live forecast
Destination
Oyster Bay, NY
Morning
in Oyster Bay on Saturday
Local time
10:45 AM
EDT
Current temp
45°F
Unavailable
Live forecast
43°F
Brookhaven, NY
34 mi in
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
3 degrees warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
1h 37m on the road
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
Frequently Asked Questions
The drive from Southampton, NY to Oyster Bay, NY covers 67.1 miles and takes about 1h 37m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Long Island Expressway, Sunrise Highway, County Road 39. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 33.6 miles from Southampton, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $11.05 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.
This drive requires moderate attention. Across 67.1 miles you will encounter 10 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
The main spots that need attention: at 1 miles (NY 27; CR 39 / County Road 39): Lane positioning matters here; at 29.2 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 29.5 miles (CR 16 / Horseblock Road): Lane positioning matters here.
Between Southampton, NY and Oyster Bay, NY, road signs point toward Cr 16 West: Yaphank, Bethpage and Syosset.
