This 101.6-mile journey from Shelter Island, NY, to Manhattan, NY, is a manageable one-day road trip, taking approximately 2 hours and 49 minutes. You'll primarily be navigating the Long Island Expressway, a major artery that makes up a significant portion of the drive. With a projected fuel cost of around $17, this route is quite budget-friendly for a trip between these two points within New York. The overall feel is that of a straightforward, highway-focused excursion, ideal for getting from point A to point B efficiently. It's a route that allows for a relatively quick transition from the eastern end of Long Island to the heart of the city.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Break Rhythm
1 planned break
A short stop every 2 to 3 hours is enough for this drive.
Midpoint
50.8 miles from Shelter Island, NY
A natural place for your longest stop of the day
, about 1h 34m into the drive
.
Main Roads
Road
Distance
Duration
Long Island Expressway
65.7 mi
1h 29m
Middle Road
11.8 mi
17m
Sound Avenue
5.3 mi
8m
Nugent Drive
3.7 mi
5m
Northville Turnpike
3.4 mi
6m
North Ferry Road
1.7 mi
3m
North Ferry
1 mi
14m
Main Road
0.9 mi
1m
Longest stretch:
Long Island Expressway
— 65.7 mi, about 1h 29m
Turn-by-Turn Driving Directions
Step-by-step road directions between Shelter Island, NY and Manhattan, NY.
1
Start on North Ferry Road
284 ft·17 sec·North Ferry Road
Toward Route 114 SOUTH, South Ferry, Sag Harbor
2
Turn left
315 ft·25 sec
3
Turn right onto NY 114
289 ft·13 sec·North Ferry Road
4
Enter roundabout onto North Ferry Road
10 ft·0 sec·North Ferry Road
Toward Route 114 NORTH, Shelter Island Heights, North Ferry, Greenport
5
Continue on North Ferry Road
0.5 mi·1 min·North Ferry Road
Toward Route 114 NORTH, Shelter Island Heights, North Ferry, Greenport
6
Continue on NY 114
0.5 mi·54 sec·North Ferry Road
7
Continue on NY 114
0.6 mi·1 min·North Ferry Road
8
Turn right onto NY 114
0.1 mi·24 sec·Cedar Avenue
Toward North Ferry
9
Turn right onto NY 114
0.2 mi·30 sec·Clinton Avenue
Toward North Ferry
10
Continue on NY 114
0.1 mi·22 sec·Summerfield Place
11
Continue on NY 114
131 ft·4 sec·Summerfield Place
12
Continue on NY 114
1.0 mi·14 min·North Ferry
13
Continue on NY 114
172 ft·5 sec·Third Street
14
Continue on NY 114
507 ft·21 sec·Third Street
15
Turn left onto NY 25
0.5 mi·1 min·Front Street
16
Continue on NY 25
0.9 mi·1 min·Main Road
17
Turn right onto Chapel Lane
0.4 mi·1 min·Chapel Lane
18
Turn left onto CR 48; Truck NY 25
12 mi·17 min·Middle Road
19
Continue on CR 48; Truck NY 25
5.3 mi·8 min·Sound Avenue
20
Turn left onto CR 43
3.4 mi·6 min·Northville Turnpike
21
At end of road, turn left onto CR 73
138 ft·12 sec·Roanoke Avenue
22
Turn right onto Railroad Avenue
0.1 mi·26 sec·Railroad Avenue
23
Turn left onto Griffing Avenue
149 ft·6 sec·Griffing Avenue
24
Turn right onto Court Street
0.2 mi·35 sec·Court Street
25
Continue on CR 94A
0.1 mi·23 sec·Center Drive Spur
26
Merge onto CR 94
3.7 mi·5 min·Nugent Drive
Use the left lane.
27
Continue on CR 94
0.3 mi·34 sec·Edwards Avenue
28
Turn left
291 ft·6 sec
Toward I 495 West: New YorkUse the left lane.
29
Continue on this road
0.3 mi·31 sec·this road
Toward I 495 West: New York
30
Merge onto I 495
66 mi·1 hr 29 min·Long Island Expressway
Use the straight / slight right lanes.
31
Take the exit
0.4 mi·43 sec
Exit 16Toward Ed Koch Queensboro Bridge, Hunters Point Avenue, Greenpoint AvenueUse the straight / slight right lanes.
32
Turn straight onto Laurel Hill Boulevard
80 ft·2 sec·Laurel Hill Boulevard
33
Keep slight right at fork onto Hunters Point Avenue
Given the 2-hour and 49-minute duration, this route is easily completed in a single day, so you have the flexibility to leave when it suits you best. However, consider departing early in the morning or later in the evening to avoid peak Long Island Expressway traffic. With only one recommended stop noted, you can plan your breaks strategically, perhaps around the halfway point. Keep an eye on your fuel levels, as the estimated cost is $17, and it's always wise to top off before heading into the dense traffic of Manhattan. A specific tip for this route is to monitor real-time traffic conditions on the Long Island Expressway as you get closer to the city, as delays can significantly impact your arrival time.
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.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 50.8 miles from Shelter Island, NY, or about 1h 34m into the drive.
The longest continuous stretch on this route runs about 65.7 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 22 miles or 51m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 50.8 miles or 1h 34m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 2h 18m
Traffic, exits, and arrival timing usually matter more near Manhattan, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Shelter Island, 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 Shelter Island, NY
This is one driving day of about 101.6 miles and 2h 49m.
Your first comfortable stop window is around 22 miles from Shelter Island, 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 Long Island Expressway for about 65.7 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 28
5 decision points cluster between mile 0.2 and 99.4 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
7
0.2 mi into trip|~0m in|North Ferry Road
Enter roundabout onto North Ferry Road toward Route 114 NORTH, Shelter Island Heights, North Ferry, Greenport
Roundabout - know your exit number before entering. Multiple destination signs - pick the right one
Toward Route 114 NORTH, Shelter Island Heights,...
8
30.2 mi into trip|~1h 5m in
Turn left toward I 495 West: New York
Lane positioning matters here
Use the left lane.
Toward I 495 West: New York
8
96.2 mi into trip|~2h 35m in
Take the exit toward Ed Koch Queensboro Bridge, Hunters Point Avenue, Greenpoint Avenue
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 16
Toward Ed Koch Queensboro Bridge, Hunters Point...
6
96.7 mi into trip|~2h 36m in|Hunters Point Avenue
Keep slight right at fork onto Hunters Point Avenue
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / slight right lanes.
7
99.4 mi into trip|~2h 42m in|NY 25
Keep slight right at fork onto NY 25 toward 60th Street West
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Toward 60th Street West
Fuel & Cost
Regular Gas
$16.72 one way
$33.45 round trip
$4.18/gal25.4 MPG avg36 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$18.08
$36.17
premium
$4.92
$19.69
$39.38
diesel
$5.61
$22.43
$44.86
Estimated Tolls: $0.24
Northville Turnpike
(3.4 mi)$0.24
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
$17
Tolls
$0
Meals
$25–$50
Total
$42–$67
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 35.5 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $11 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
30.5
0
$10.67
$4.88
Efficient EV
25.4
0
$8.89
$4.06
EV Truck/SUV
40.6
0
$14.22
$6.50
Gas CO2
36 kg
EV CO2
12 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 14, 2026
Origin
Shelter Island, NY
Morning
in Shelter Island on Sunday
Local time
10:40 AM
EDT
Current temp
80°F
Mostly Sunny
S 8 mph8% chanceLive forecast
Flood Warning
Flood Warning issued April 14 at 12:03PM EDT by NWS Binghamton NY
Destination
Manhattan, NY
Morning
in Manhattan on Sunday
Local time
10:40 AM
EDT
Current temp
49°F
Unavailable
Live forecast
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
31 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
2h 49m on the road
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
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.
General Grant National Memorial
National Memorial
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...
2 mi from route
~5 min detour
Free
near mile 101.6
Caution: Lower Crypt Access Subject to Safe Conditions
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...
3 mi from route
~6 min detour
Free
near mile 101.6
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...
4 mi from route
~10 min detour
Free
near mile 98.1
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...
5 mi from route
~13 min detour
Free
near mile 98.1
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...
5 mi from route
~12 min detour
Free
near mile 98.1
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a highway-focused experience on this route, with 68% of the drive utilizing major roadways. Your longest uninterrupted stretch will be 65.7 miles along the Long Island Expressway, offering a consistent cruising pace. While the main roads like the Long Island Expressway, Middle Road, and Sound Avenue provide a direct path, the character leans heavily towards efficient travel rather than winding scenic byways. This means you'll likely encounter substantial traffic, especially as you approach Manhattan, so be prepared for a more urban driving environment towards the end of your trip.
68% highway — fuel and pacing are the main things to plan.
46 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 65.7 mi on Long Island Expressway.
How Hard Is This Drive?
9/10
This is a straightforward highway drive that stays mostly on Long Island Expressway and Middle Road. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 0.2 miles in near North Ferry Road.
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 28 significant decision points across 101.6 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 0.2 miles (North Ferry Road): Roundabout - know your exit number before entering. Multiple destination signs - pick the right one; at 30.2 miles: Lane positioning matters here; at 96.2 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Wall Street. Madison Avenue. 34th Street. Broadway. Times Square. Manhattan is so well known that even the names of its streets have become iconic and understood the world over. This long, thin island is only one of New York City's five boroughs, but it's Manhattan that has the concrete canyons and the inimitable skyline; Manhattan that has the world's brightest theater district; Manhattan that has Central Park, Rockefeller Center, the Empire State Building, and the Met; and Manhattan that includes iconic neighborhoods like Harlem, the Upper East Side, Times Square, and Greenwich Village.
The rest of New York City has much to see and do, but it's Manhattan that represents the city—and sometimes the entire United States—to the world. You could spend a month on this tiny island and still not see all there is to see.
Top landmarks
•Empire State Building — skyscraper located in Midtown Manhattan, New York City, USA
Doable as a same-day drive at 2h 49m. Total distance: 101.6 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
2h 49m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (68%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 65.7 miles on Long Island Expressway. The full list of main roads is in the Roads section above.
Expect about $0.24 in tolls one way, starting with Northville Turnpike. 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.
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 Manhattan, 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 0.2 miles (North Ferry Road): Roundabout - know your exit number before entering. Multiple destination signs - pick the right one; at 30.2 miles: Lane positioning matters here; at 96.2 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — General Grant National Memorial, Hamilton Grange National Memorial and Stonewall National Monument (6 total within detour distance). See the National Parks section for detour distances and tips on detours.
Yes. A round trip is manageable in a single day if you plan a break at Manhattan, NY before heading back.
