Spanning 265.9 miles, this trip from Southport to Oyster Bay is a manageable journey that typically takes about 4 hours and 38 minutes behind the wheel. Because the route is categorized as a turn-heavy local drive rather than a highway sprint, it is best approached as a focused one-day excursion. You should budget approximately $43 for fuel to cover the distance across the Northeast. While the drive is straightforward enough to complete in a single sitting, the nature of the local roads means your pace will be dictated by turns rather than cruising speed. It is a practical choice for those who prefer navigating local thoroughfares over monotonous interstate travel.
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
131.8 miles from Southport, NY
A natural place for your longest stop of the day
, about 2h 37m into the drive
.
Main Roads
Road
Distance
Duration
Keystone Shortway
80 mi
1h 37m
Southern Tier Expressway
58.7 mi
1h 9m
I 81
53.4 mi
1h 3m
I 380
23.6 mi
25m
Northern Boulevard
14.5 mi
24m
Cross Bronx Expressway
6.6 mi
8m
Christopher Columbus Highway
5.5 mi
5m
I 84
3.7 mi
4m
Longest stretch:
Keystone Shortway
— 80 mi, about 1h 37m
Turn-by-Turn Driving Directions
Step-by-step road directions between Southport, NY and Oyster Bay, NY.
1
Start on NY 14
272 ft·5 sec·Clemens Center Parkway
2
Continue on NY 14
2.5 mi·4 min·Clemens Center Parkway
3
Turn right onto Pennsylvania Avenue
0.2 mi·21 sec·Pennsylvania Avenue
4
Turn straight onto Sly Street
0.2 mi·22 sec·Sly Street
5
Continue on Madison Avenue
460 ft·11 sec·Madison Avenue
6
Turn right onto NY 352
0.8 mi·1 min·East Water Street
7
Take the ramp
0.3 mi·32 sec
8
Merge onto I 86; NY 17
59 mi·1 hr 9 min·Southern Tier Expressway
9
Keep slight right at fork onto I 81
53 mi·1 hr 3 min·I 81
Toward I 81 South: ScrantonUse the straight lane.
10
Keep slight right at fork onto US 6
0.8 mi·1 min·US 6
Exit 187Toward I 84 East, I 380 South, US 6 East: Carbondale, Mt PoconoUse the slight left / slight right lanes.
11
Continue on I 84; I 380
3.7 mi·4 min·I 84; I 380
Toward I 84 East, I 380 South: Mount Pocono, MilfordUse the straight lane.
12
Keep slight right at fork onto I 380
24 mi·25 min·I 380
Exit 4Toward I 380 South: Mount Pocono
13
Keep slight left at fork
1.0 mi·1 min
Exit 1BToward I 80 East: Stroudsburg
14
Merge onto I 80
80 mi·1 hr 37 min·Keystone Shortway
Use the straight / right lanes.
15
Keep slight right at fork onto I 80
5.5 mi·5 min·Christopher Columbus Highway
Toward I 95: George Washington Bridge Lower LevelUse the slight right lane.
16
Keep slight left at fork
0.3 mi·23 sec
Toward I 95 North: George Washington Bridge, New York CityUse the straight / slight right lanes.
17
Keep slight right at fork
0.4 mi·38 sec
Exit 70A-BToward Leonia, TeaneckUse the slight right lane.
18
Turn right
0.2 mi·35 sec
Exit 70AToward LeoniaUse the straight / slight right lanes.
19
Turn straight onto CR 56
454 ft·9 sec·Degraw Avenue
20
Continue on CR 56
1.1 mi·2 min·Fort Lee Road
Use the straight / right lanes.
21
Continue on CR 56
469 ft·13 sec·Main Street
22
Take the ramp
472 ft·12 sec
Toward George Washington Bridge
23
Merge onto US 1; US 9; US 46
0.3 mi·28 sec·Bergen Boulevard
Use the straight / slight right lanes.
24
Take the exit
312 ft·4 sec
Toward George Washington Bridge Upper Level
25
Merge onto I 95 EXPR
0.3 mi·20 sec·I 95 EXPR
Use the straight / slight right lanes.
26
Keep slight left at fork onto I 95 EXPR
0.8 mi·1 min·I 95 EXPR
27
Continue on I 95; US 1; US 9
0.6 mi·1 min·George Washington Bridge (upper level)
Use the straight / slight right lanes.
28
Continue on I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
29
Continue on I 95; US 1
4.7 mi·6 min·Cross Bronx Expressway
Use the straight / slight right lanes.
30
Keep slight right at fork onto I 295
2.0 mi·2 min·Cross Bronx Expressway
Exit 6BToward I 295 South: Throgs Neck BridgeUse the straight / slight left lanes.
31
Merge onto I 295
0.6 mi·58 sec·Throgs Neck Expressway
32
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
Use the straight / slight right lanes.
33
Continue on I 295
2.0 mi·2 min·Clearview Expressway
Use the straight / slight right lanes.
34
Take the exit
0.2 mi·32 sec
Exit 5Toward NY 25A: Northern BoulevardUse the straight / slight right lanes.
35
Continue on Clearview Expressway
457 ft·17 sec·Clearview Expressway
36
Turn left onto NY 25A
15 mi·24 min·Northern Boulevard
Use the left lane.
37
Turn left onto NY 106
0.3 mi·29 sec·Jericho Oyster Bay Road
38
Turn straight onto NY 106
0.5 mi·46 sec·Oyster Bay Road
39
Keep slight left at fork onto NY 106
260 ft·4 sec·Oyster Bay Road
40
Continue on NY 106
0.9 mi·1 min·Pine Hollow Road
Use the left lane.
41
Continue on NY 106
105 ft·5 sec·South Street
42
Turn right onto Berry Hill Road
112 ft·9 sec·Berry Hill Road
43
Continue on Berry Hill Road
64 ft·2 sec·Berry Hill Road
44
Arrive at destination
Berry Hill Road
Trip Plan
Since this is a turn-heavy local drive, plan to depart early in the day to avoid peak congestion on the smaller roads that make up your path. With a single stop planned for the 4-hour and 38-minute journey, use that time to stretch and refuel while keeping your $43 fuel budget in mind. Because the entire route relies on local streets, stay alert for frequent speed limit changes and turning opportunities that aren't present on standard interstates. Flexibility is your biggest advantage here, so don't hesitate to adjust your pacing if local traffic slows your progress. Keep a navigation app running consistently to stay on track through the complex turns of Clemens Center Parkway and Sly Street.
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 131.8 miles from Southport, NY, or about 2h 37m into the drive.
The longest continuous stretch on this route runs about 80 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 10m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 131.8 miles or 2h 37m 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 18m
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 Southport, 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 Southport, NY
This is one driving day of about 263.6 miles and 5h 28m.
Your first comfortable stop window is around 58 miles from Southport, 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 Keystone Shortway for about 80 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 26
5 decision points cluster between mile 62.8 and 240.4 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
7
62.8 mi into trip|~1h 16m in|I 81
Keep slight right at fork onto I 81 toward I 81 South: Scranton
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight lane.
Toward I 81 South: Scranton
9
116.2 mi into trip|~2h 19m in|US 6
Keep slight right at fork onto US 6 toward I 84 East, I 380 South, US 6 East: Carbondale, Mt Pocono
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left / slight right lanes.
Exit 187
Toward I 84 East, I 380 South, US 6 East: Carbo...
8
230.8 mi into trip|~4h 35m in
Keep slight left at fork toward I 95 North: George Washington Bridge, New York City
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 95 North: George Washington Bridge, Ne...
9
231 mi into trip|~4h 36m in
Keep slight right at fork toward Leonia, Teaneck
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 70A-B
Toward Leonia, Teaneck
8
240.4 mi into trip|~4h 50m in|I 295 / Cross Bronx Expressway
Keep slight right at fork onto I 295 / Cross Bronx Expressway toward I 295 South: Throgs Neck Bridge
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight left lanes.
Exit 6B
Toward I 295 South: Throgs Neck Bridge
Fuel & Cost
Regular Gas
$43.39 one way
$86.78 round trip
$4.18/gal25.4 MPG avg92 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$46.92
$93.84
premium
$4.92
$51.09
$102.18
diesel
$5.61
$58.20
$116.40
Estimated Tolls: $22.55
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
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: 92.2 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
$27.68
$12.65
Efficient EV
65.9
0
$23.07
$10.54
EV Truck/SUV
105.4
1
$36.90
$16.87
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
Southport, NY
Late night
in Southport on Sunday
Local time
4:53 AM
EDT
Current temp
41°F
Unavailable
Live forecast
Destination
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
Flood Warning
Flood Warning issued April 15 at 11:57PM EDT by NWS Binghamton NY
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 warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
5h 28m 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...
2 mi from route
~6 min detour
Free
near mile 236.3
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...
3 mi from route
~8 min detour
Free
near mile 236.3
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
~22 min detour
Free
near mile 236.3
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 236.3
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
~28 min detour
Free
near mile 236.3
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...
11 mi from route
~27 min detour
Free
near mile 236.3
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a technical experience behind the wheel, as this route features a 0% highway share and relies entirely on local roads like Clemens Center Parkway, Pennsylvania Avenue, and Sly Street. Unlike high-speed transit, this journey demands your full attention due to the high frequency of turns throughout the 265.9-mile transit. The road profile is consistent, prioritizing local connectivity over long, uninterrupted stretches of pavement. You will find that the lack of highway miles keeps the driving environment varied and engaging, though it does mean you will spend the entire duration navigating intersections and local traffic patterns.
58% highway, the rest on surface roads — varied driving throughout.
44 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 80 mi on Keystone Shortway.
How Hard Is This Drive?
9/10
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 62.8 miles in near I 81.
Driving Effort9/10
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 26 significant decision points across 263.6 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 62.8 miles (I 81): Highway fork - watch signs carefully. Lane positioning matters here; at 116.2 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 230.8 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Southport, NY and Oyster Bay, NY, road signs point toward Mt Pocono, Milford, New York City, Leonia, Teaneck and George Washington Bridge Upper Level.
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 28m. Total distance: 263.6 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 28m drive, comfortable solo distance.
Scenic Drive
Mixed highway & surface route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 80 miles on Keystone Shortway. The full list of main roads is in the Roads section above.
Expect about $22.55 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 Oyster Bay, 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 62.8 miles (I 81): Highway fork - watch signs carefully. Lane positioning matters here; at 116.2 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 230.8 miles: Highway fork - watch signs carefully. 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 10.9 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Oyster Bay, NY before the return drive.
