The drive from Oyster Bay, NY to Southampton, NY covers 67.3 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, Captain Daniel Roe Highway for much of the mileage,
and the overall profile is mixed drive.
The longest uninterrupted segment is about 37.1 miles on Long Island Expressway.
At current regular gas prices, budget about $11.08 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
33.7 miles from Oyster Bay, NY
A natural place for your longest stop of the day
, about 48m 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: 67.3 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 (57%). Some complex stretches to watch for.
Scenic Drive
Mixed drive route profile with national parks nearby.
Drive Character
The drive from Oyster Bay, NY to Southampton, NY covers 67.3 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 20 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 37.1 miles.
Elevation Profile
Mostly flat terrain
194 ft15 ft
Total Climb
246 ft
Total Descent
265 ft
Highest Point
194 ft
~4.8 mi in
Elevation Range
179 ft
How Hard Is This Drive?
This route mixes highway mileage with some local-road sections near the start or finish. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 0.1 miles in near NY 106 / South Street.
Driving Effort7/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 67.3 miles you will encounter 12 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 0.1 miles (NY 106 / South Street): Sharp turn - reduce speed on approach; at 4.8 miles (NY 25 / Jericho Turnpike): Lane positioning matters here; at 5.6 miles (NY 135 / Seaford-Oyster Bay Expressway): Merge point - match speed before joining. Lane positioning matters here.
Critical Maneuvers
5 of 12 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
6
0.1 mi into trip|~0m in|NY 106 / South Street
Turn sharp left onto NY 106 / South Street
Sharp turn - reduce speed on approach
6
4.8 mi into trip|~9m in|NY 25 / Jericho Turnpike
Turn left onto NY 25 / Jericho Turnpike
Lane positioning matters here
Use the left lane.
5
5.6 mi into trip|~10m in|NY 135 / Seaford-Oyster Bay Expressway
Merge onto NY 135 / Seaford-Oyster Bay Expressway
Merge point - match speed before joining. Lane positioning matters here
Use the straight / slight right lanes.
7
6.2 mi into trip|~11m in
Take the exit toward I 495 East: Riverhead
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the right lane.
Exit 13E
Toward I 495 East: Riverhead
8
43.6 mi into trip|~1h 1m in
Take the exit toward CR 111: Manorville, Eastport
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 70
Toward CR 111: Manorville, Eastport
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Oyster Bay, NY and Southampton, NY, road signs point toward Cr 111: Manorville and Eastport.
Cr 111: Manorville
43.6 mi in|~1h 1m
Eastport
43.6 mi in|~1h 1m
Main Roads
Road
Distance
Duration
Long Island Expressway
37.1 mi
50m
Sunrise Highway
13.2 mi
15m
Captain Daniel Roe Highway
4.6 mi
7m
County Road 39
4 mi
8m
Split Rock Road
1.8 mi
3m
Jackson Avenue
1 mi
2m
Sugar Toms Lane
0.9 mi
1m
Pine Hollow Road
0.9 mi
1m
Longest stretch:
Long Island Expressway
— 37.1 mi, about 50m
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay, NY and Southampton, NY.
1
Start on Berry Hill Road
288 ft·21 sec·Berry Hill Road
2
Turn sharp left onto NY 106
429 ft·9 sec·South Street
3
Continue on NY 106
0.9 mi·1 min·Pine Hollow Road
4
Turn left onto Sugar Toms Lane
0.9 mi·1 min·Sugar Toms Lane
5
Continue on Split Rock Road
1.8 mi·3 min·Split Rock Road
6
Turn slight right onto Berry Hill Road
283 ft·7 sec·Berry Hill Road
7
Turn straight onto Jackson Avenue
1.0 mi·2 min·Jackson Avenue
8
Turn left onto NY 25
0.4 mi·36 sec·Jericho Turnpike
Use the left lane.
9
Take the ramp
0.3 mi·43 sec
Toward NY 135 South: Seaford
10
Merge onto NY 135
0.6 mi·37 sec·Seaford-Oyster Bay Expressway
Use the straight / slight right lanes.
11
Take the exit
0.3 mi·39 sec
Exit 13EToward I 495 East: RiverheadUse the right lane.
12
Merge onto I 495
37 mi·50 min·Long Island Expressway
Use the straight / right lanes.
13
Take the exit
0.3 mi·36 sec
Exit 70Toward CR 111: Manorville, EastportUse the straight / slight right lanes.
14
Turn right onto CR 111
4.6 mi·7 min·Captain Daniel Roe Highway
Use the right lane.
15
Take the exit
0.6 mi·49 sec
Toward NY 27 East: Montauk
16
Merge onto NY 27
13 mi·15 min·Sunrise Highway
17
Continue on NY 27; CR 39
4.0 mi·8 min·County Road 39
18
Turn right onto North Sea Road
0.7 mi·1 min·North Sea Road
Use the right lane.
19
Continue on Main Street
0.3 mi·1 min·Main Street
Use the straight / left / right lanes.
20
Arrive at destination
Main Street
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 33.7 miles from Oyster Bay, NY, or about 48m into the drive.
The longest continuous stretch on this route runs about 37.1 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 15 miles or 23m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 33.7 miles or 48m 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 19m
Traffic, exits, and arrival timing usually matter more near Southampton, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Oyster Bay, NY so your first major turns are already loaded.
Day 1
Settle into the route from Oyster Bay, NY
This is one driving day of about 67.3 miles and 1h 37m.
Your first comfortable stop window is around 15 miles from Oyster Bay, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on Long Island Expressway for about 37.1 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 33.7 mi from Oyster Bay, NY
· 48m into the drive
The midpoint is around 33.7 miles from Oyster Bay, NY, which is a good place for a longer meal and fuel stop.
Arriving in Southampton, NY
The final approach into Southampton, NY usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
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...
9 mi from route
~22 min detour
Free
near mile 32.5
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...
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...
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...
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...
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...
Park data from the National Park Service API. Alerts update every 2 hours.
Fuel & Cost
Regular Gas
$11.08 one way
$22.16 round trip
$4.18/gal25.4 MPG avg24 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$11.98
$23.96
premium
$4.92
$13.04
$26.09
diesel
$5.61
$14.86
$29.72
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
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
20.2
0
$7.07
$3.23
Efficient EV
16.8
0
$5.89
$2.69
EV Truck/SUV
26.9
0
$9.42
$4.31
Gas CO2
24 kg
EV CO2
8 kg (67% 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 16, 2026
Origin
Oyster Bay, NY
Morning
in Oyster Bay on Saturday
Local time
11:49 AM
EDT
Current temp
45°F
Unavailable
Live forecast
Destination
Southampton, NY
Morning
in Southampton on Saturday
Local time
11:49 AM
EDT
Current temp
42°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 cooler 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 Oyster Bay, NY to Southampton, NY covers 67.3 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, Captain Daniel Roe Highway. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 33.7 miles from Oyster Bay, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $11.08 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 67.3 miles you will encounter 12 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 0.1 miles (NY 106 / South Street): Sharp turn - reduce speed on approach; at 4.8 miles (NY 25 / Jericho Turnpike): Lane positioning matters here; at 5.6 miles (NY 135 / Seaford-Oyster Bay Expressway): Merge point - match speed before joining. Lane positioning matters here.
Between Oyster Bay, NY and Southampton, NY, road signs point toward Cr 111: Manorville and Eastport.
Mostly flat terrain. The route ranges from 15 ft to 194 ft elevation with about 246 ft of total climbing.
Yes. Nearby national parks include Fire Island National Seashore, Hamilton Grange National Memorial and General Grant National Memorial. There are 6 parks within detour distance of this route.
