Spanning 263.8 miles, your journey from Oyster Bay to Southport takes approximately 5 hours and 29 minutes of active driving time. Because this route relies on local roads rather than major interstates, it functions best as a single-day trip if you are comfortable with a steady pace behind the wheel. Expect to budget around $43 for fuel to cover the distance between these two Northeast locations. You will navigate primarily via South Street, Pine Hollow Road, and Oyster Bay Road as you transition from the coastal environment of Oyster Bay toward the interior of the state. It is a straightforward trip, though the lack of highway miles means you should plan for a consistent, rather than high-speed, travel experience.
Trip Pace
Same-day drive is realistic
A same-day return is possible, but it will make for a full day on the road.
Break Rhythm
1 planned break
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
131.9 miles from Oyster Bay, NY
A natural place for your longest stop of the day
, about 2h 52m into the drive
.
Main Roads
Road
Distance
Duration
Christopher Columbus Highway
68.2 mi
1h 20m
I 81
58.1 mi
1h 9m
I 86
54.7 mi
1h 4m
I 380
27.7 mi
30m
Keystone Shortway
17.3 mi
24m
Northern Boulevard
13.4 mi
22m
Cross Bronx Expressway
6.6 mi
8m
Clemens Center Parkway
2.5 mi
3m
Longest stretch:
Christopher Columbus Highway
— 68.2 mi, about 1h 20m
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay, NY and Southport, 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
Continue on NY 106
0.7 mi·1 min·Oyster Bay Road
5
Turn right onto NY 25A
13 mi·22 min·Northern Boulevard
Use the left lane.
6
Take the ramp
0.2 mi·28 sec
Toward Cross Island Parkway North, Whitestone BridgeUse the right lane.
7
Merge onto CI
2.3 mi·3 min·Cross Island Parkway
Use the straight / slight right lanes.
8
Take the exit
0.6 mi·1 min
Exit 33Toward I 295 North: Throgs Neck Bridge, Bronx, New EnglandUse the straight / slight right lanes.
9
Merge onto I 295
1.8 mi·3 min·Throgs Neck Bridge
10
Continue on I 295
0.7 mi·1 min·Throgs Neck Expressway
Use the straight / slight right lanes.
11
Keep slight left at fork onto I 295
6.6 mi·8 min·Cross Bronx Expressway
Use the straight / slight right lanes.
12
Keep slight left at fork onto I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
Toward Upper Level
13
Continue on I 95; US 1
0.6 mi·59 sec·George Washington Bridge (upper level)
14
Continue on I 95 EXPR; US 1 EXPR; US 9 EXPR
0.5 mi·48 sec·I 95 EXPR; US 1 EXPR; US 9 EXPR
15
Keep slight left at fork onto I 95 EXPR; US 1 EXPR; US 9 EXPR
0.6 mi·39 sec·I 95 EXPR; US 1 EXPR; US 9 EXPR
Use the straight / slight right lanes.
16
Keep slight left at fork onto I 95 EXPR; NJTP
0.1 mi·8 sec·I 95 EXPR; NJTP
17
Take the exit
0.2 mi·22 sec
Toward I 95 South, NJTP South: HackensackUse the straight / slight right lanes.
18
Keep slight left at fork
0.4 mi·29 sec
Toward I 95 South, NJTP South: HackensackUse the slight left / slight right lanes.
19
Merge onto I 95; NJTP
2.0 mi·2 min·New Jersey Turnpike
Use the straight / slight right lanes.
20
Take the exit
0.8 mi·1 min
Exit 69Toward I 80 West: Paterson, HackensackUse the straight / slight right lanes.
21
Continue on I 80
68 mi·1 hr 20 min·Christopher Columbus Highway
Use the straight / slight right lanes.
22
Keep slight left at fork onto I 80
5.5 mi·8 min·Keystone Shortway
Use the straight / slight right lanes.
23
Keep slight left at fork onto I 80
12 mi·15 min·Keystone Shortway
24
Take the exit
0.7 mi·46 sec
Exit 293Toward I 380 North: Scranton
25
Continue on I 380
28 mi·30 min·I 380
Use the straight lane.
26
Merge onto I 81
58 mi·1 hr 9 min·I 81
Use the straight lane.
27
Keep slight left at fork onto I 86; NY 17
55 mi·1 hr 4 min·I 86; NY 17
Toward I 86: Corning
28
Take the exit
0.2 mi·27 sec
Exit 56Toward NY 352: Elmira, Jerusalem Hill
29
Keep slight left at fork
103 ft·6 sec
30
Turn left onto NY 352
0.8 mi·1 min·East Water Street
31
Turn left onto Madison Avenue
460 ft·9 sec·Madison Avenue
32
Continue on Sly Street
0.2 mi·22 sec·Sly Street
33
Continue on Pennsylvania Avenue
0.2 mi·23 sec·Pennsylvania Avenue
34
Turn left onto NY 14
2.5 mi·3 min·Clemens Center Parkway
35
Arrive at destination
NY 14
Trip Plan
To make the most of this 5.5-hour trek, plan for at least one dedicated stop to stretch your legs and reset. Since the route is entirely local, traffic patterns on South Street or Pine Hollow Road can significantly impact your arrival time; consider departing early in the morning to avoid local congestion. Keep your $43 fuel budget in mind when planning your refueling intervals, as local roads may offer different station availability than major highways. Given the turn-heavy profile of the drive, ensure your vehicle’s tire pressure and fluids are checked before leaving Oyster Bay. Taking advantage of the route’s flexibility allows you to pull over whenever you need, so don't feel pressured to rush the drive in one sitting.
Morning Departure
An early start around 7-8 AM gets you there with plenty of daylight left.
Evening Departure
A late afternoon start means arriving after dark. Morning is better.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 131.9 miles from Oyster Bay, NY, or about 2h 52m into the drive.
The longest continuous stretch on this route runs about 68.2 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 58 miles or 1h 21m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 131.9 miles or 2h 52m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 4h 31m
Traffic, exits, and arrival timing usually matter more near Southport, 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.
+
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 Oyster Bay, NY
This is one driving day of about 263.8 miles and 5h 29m.
Your first comfortable stop window is around 58 miles from Oyster Bay, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 1 real break rather than only quick fuel stops.
The longest stretch is on Christopher Columbus Highway for about 68.2 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 23
5 decision points cluster between mile 15.1 and 32.4 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
7
15.1 mi into trip|~25m in
Take the ramp toward Cross Island Parkway North, Whitestone Bridge
Lane positioning matters here. Multiple destination signs - pick the right one
Use the right lane.
Toward Cross Island Parkway North, Whitestone B...
8
17.6 mi into trip|~29m in
Take the exit toward I 295 North: Throgs Neck Bridge, Bronx, New England
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 33
Toward I 295 North: Throgs Neck Bridge, Bronx,...
8
29.8 mi into trip|~47m in
Take the exit toward I 95 South, NJTP South: Hackensack
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.
Toward I 95 South, NJTP South: Hackensack
8
30.1 mi into trip|~48m in
Keep slight left at fork toward I 95 South, NJTP South: Hackensack
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left / slight right lanes.
Toward I 95 South, NJTP South: Hackensack
8
32.4 mi into trip|~51m in
Take the exit toward I 80 West: Paterson, Hackensack
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 69
Toward I 80 West: Paterson, Hackensack
Fuel & Cost
Regular Gas
$43.42 one way
$86.85 round trip
$4.18/gal25.4 MPG avg92 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$46.95
$93.91
premium
$4.92
$51.13
$102.26
diesel
$5.61
$58.24
$116.49
Estimated Tolls: $22.83
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
New Jersey Turnpike
(2 mi)$0.28
Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.
Estimated Trip Cost (one way, 1 person)
Fuel
$43
Tolls
$23
Meals
$25–$50
Total
$91–$116
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 92.3 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $28 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
79.1
0
$27.70
$12.66
Efficient EV
66
0
$23.08
$10.55
EV Truck/SUV
105.5
1
$36.93
$16.88
Gas CO2
92 kg
EV CO2
31 kg (66% less)
Plan for 0 charging stops, roughly every 270 miles. Allow 25-40 minutes per stop at a DC fast charger.
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
Late night
in Oyster Bay on Sunday
Local time
4:53 AM
EDT
Current temp
86°F
Mostly Sunny
SW 6 to 12 mph4% chanceLive forecast
Destination
Southport, NY
Late night
in Southport on Sunday
Local time
4:53 AM
EDT
Current temp
41°F
Unavailable
Live forecast
49°F
Ramapo, NY
132 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
45 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
5h 29m on the road
An early start around 7-8 AM gets you there with plenty of daylight left.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
National Parks Near This Route
Worth a detour if your schedule allows.
Hamilton Grange National Memorial
National Memorial
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...
9 mi from route
~21 min detour
Free
near mile 27.3
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...
10 mi from route
~25 min detour
Free
near mile 27.3
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...
10 mi from route
~26 min detour
Free
near mile 27.3
Located at the southern tip of Manhattan, Castle Clinton marks the place where New York City began and reflects the growth of both the city and the nation. Built to defend the harbor during the War of...
11 mi from route
~27 min detour
Free
near mile 27.3
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Forget the monotony of the interstate; this route is defined by its turn-heavy, local nature. With a 0% highway share, you will spend the entire 263.8 miles navigating surface roads that demand your full attention. The road's personality is technical and winding, requiring you to stay alert through constant changes in direction. Because the route avoids high-speed corridors, you won't encounter long, straight stretches that allow for cruise control. Instead, you can expect a hands-on driving experience that keeps you engaged with the local landscape from start to finish.
59% highway, the rest on surface roads — varied driving throughout.
35 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 68.2 mi on Christopher Columbus Highway.
How Hard Is This Drive?
10/10
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 15.1 miles in.
Driving Effort10/10
High effort - long or complex enough to need steady focus all day
Balances navigation complexity with total wheel time.
This is a demanding drive. With 23 significant decision points across 263.8 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 15.1 miles: Lane positioning matters here. Multiple destination signs - pick the right one; at 17.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 29.8 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Elevation Profile
Gently rolling terrain
1,808 ft-5 ft
Total Climb
2,176 ft
Total Descent
1,328 ft
Highest Point
1,808 ft
~131.9 mi in
Elevation Range
1,814 ft
Notable High Points
1,808 ft at ~131.9 miles+843 ft prominence
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 Southport, NY, road signs point toward Cross Island Parkway North, Bronx, New England, Upper Level, Njtp South: Hackensack and Hackensack.
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.
Top landmarks
•Christ Church — historic Episcopal parish in Oyster Bay, New York, USA
Doable as a same-day drive at 5h 29m. Total distance: 263.8 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 29m drive, comfortable solo distance.
Scenic Drive
Mixed highway & surface route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 68.2 miles on Christopher Columbus Highway. The full list of main roads is in the Roads section above.
Expect about $22.83 in tolls one way, starting with George Washington Bridge. Most Northeast and Midwest toll agencies accept E-ZPass; in the West and Texas, transponders like TxTag or FasTrak apply. If you do not have a transponder, cashless tolling plates will mail a bill to the vehicle's registered address — usually with a surcharge, so a rental-car toll pass is often cheaper than paying by mail.
We did not find dedicated rest areas on this route. For a drive this long, plan bathroom and stretch breaks around gas stations, fast-food stops, or small-town downtowns — check the Nearby Places section for options.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Southport, NY before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 1 meaningful breaks. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 15.1 miles: Lane positioning matters here. Multiple destination signs - pick the right one; at 17.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 29.8 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — Hamilton Grange National Memorial, General Grant National Memorial and Stonewall National Monument (6 total within detour distance). See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 5.5 hours each way, a round trip means 11.0 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Southport, NY before the return drive.
