The drive from Islip, NY to Darien, NY covers 399 miles and takes about 8h 13m behind the wheel.
It usually feels better as a 2-day road trip than as one long push.
The route leans on I 86, Christopher Columbus Highway, I 81 for much of the mileage,
and the overall profile is highway-focused drive.
The longest uninterrupted segment is about 100 miles on I 86.
At current regular gas prices, budget about $65.68 one way before food or hotel costs.
Trip Pace
Best split across 2 days
Treat the return leg as its own travel day rather than an afterthought.
Break Rhythm
2 planned breaks
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
199.5 miles from Islip, NY
A natural place for your longest stop of the day
, about 4h 10m into the drive
.
Islip (pronounced "ICE-lip") is a town on Long Island in the state of New York. Located within Suffolk County, the Town of Islip includes the villages of Brightwaters, Islandia, Ocean Beach and Saltaire. It also includes numerous hamlets including Bay Shore and Sayville which are ferry terminals for Fire Island. Other prominent communities are Bayport, Brentwood, Central Islip, Hauppauge, Islip village (the town seat), and Ronkonkoma.
Top landmarks
•Bayport Aerodrome — airport in Suffolk County, New York, United States
•Connetquot River State Park Preserve — state park in New York
•Modesty — oyster-dredging sloop built in Long Island
This is a 8h 13m highway drive covering 399 miles, with most of the trip on I 86 and Christopher Columbus Highway. The longest continuous stretch is about 100 miles on I 86.
Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 56 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
I 86 is the longest continuous segment at about 100 miles.
How Hard Is This Drive?
This is a straightforward highway drive that stays mostly on I 86 and Christopher Columbus Highway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 3.6 miles in near CR 57 / Howells Road.
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 34 significant decision points across 399 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 3.6 miles (CR 57 / Howells Road): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 31.1 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 31.2 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Critical Maneuvers
5 of 34 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
9
3.6 mi into trip|~6m in|CR 57 / Howells Road
Keep slight right at fork onto CR 57 / Howells Road toward Howells Road, Deer Park
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the right lane.
Toward Howells Road, Deer Park
8
31.1 mi into trip|~43m in
Keep slight left at fork toward NY 24 West: Hempstead Avenue
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / slight right lanes.
Toward NY 24 West: Hempstead Avenue
8
31.2 mi into trip|~43m in
Keep slight right at fork toward Hempstead Avenue West
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / slight right lanes.
Toward Hempstead Avenue West
8
50 mi into trip|~1h 10m 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
50.3 mi into trip|~1h 11m 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
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Islip, NY and Darien, NY, road signs point toward Cross Island Parkway North, Hempstead Avenue West, Grandstand, Upper Level, Njtp South: Hackensack and Hackensack - among others.
Cross Island Parkway North
29.4 mi in|~40m
Hempstead Avenue West
31.1 mi in|~43m
Grandstand
31.3 mi in|~43m
Upper Level
47.5 mi in|~1h 6m|via I 95; US 1
Njtp South: Hackensack
50 mi in|~1h 10m
Hackensack
52.6 mi in|~1h 14m
Letchworth Park
364 mi in|~7h 22m
Main Roads
Road
Distance
Duration
I 86
100 mi
1h 56m
Christopher Columbus Highway
68.2 mi
1h 20m
I 81
58.1 mi
1h 9m
Genesee Expressway
38.6 mi
44m
I 380
27.7 mi
30m
Southern State Parkway
24.7 mi
31m
Keystone Shortway
17.3 mi
24m
Genesee Street
8.7 mi
13m
Longest stretch:
I 86
— 100 mi, about 1h 56m
Turn-by-Turn Driving Directions
Step-by-step road directions between Islip, NY and Darien, NY.
1
Start on NY 27A
0.8 mi·1 min·Main Street
2
Continue on Montauk Highway
0.2 mi·19 sec·Montauk Highway
3
Continue on NY 27A
1.1 mi·1 min·Main Street
4
Turn right onto 3rd Avenue
0.6 mi·1 min·3rd Avenue
5
Continue on CR 57
0.3 mi·36 sec·Rossevelt Street
6
Continue on CR 57
0.7 mi·1 min·Howells Road
Use the left lane.
7
Turn straight onto Sunrise Highway
163 ft·3 sec·Sunrise Highway
8
Keep slight right at fork onto CR 57
0.3 mi·36 sec·Howells Road
Toward Howells Road, Deer ParkUse the right lane.
9
Continue on CR 57
0.6 mi·1 min·Bay Shore Road
10
Take the ramp
0.1 mi·19 sec
Toward SO West: New York
11
Continue on this road
363 ft·8 sec·this road
12
Merge onto SO
25 mi·31 min·Southern State Parkway
Use the straight / right lanes.
13
Take the exit
0.3 mi·43 sec
Toward Cross Island Parkway North, Whitestone BridgeUse the slight right lane.
14
Merge onto CI
1.3 mi·1 min·Cross Island Parkway
15
Take the exit
317 ft·9 sec
Exit 26BToward NY 24: UBS Arena-Belmont ParkUse the slight right lane.
16
Keep slight left at fork
437 ft·12 sec
Toward NY 24 West: Hempstead AvenueUse the slight left / slight right lanes.
17
Keep slight right at fork
0.1 mi·15 sec
Toward Cross Island Parkway North, Hempstead Avenue West
18
Keep slight right at fork
266 ft·8 sec
Toward Hempstead Avenue WestUse the slight left / slight right lanes.
19
Continue on this road
0.1 mi·13 sec·this road
Toward Grandstand, Hempstead Avenue West
20
Keep slight left at fork
100 ft·4 sec
Toward Hempstead Avenue
21
Turn right onto NY 24
1.0 mi·2 min·Hempstead Avenue
Use the right lane.
22
Turn left onto Jamaica Avenue
0.1 mi·17 sec·Jamaica Avenue
23
Turn right onto NY 24
0.7 mi·1 min·212th Street
24
Continue on I 295
5.0 mi·5 min·Clearview Expressway
Toward I 295 North: Clearview Expressway, Through Neck BridgeUse the straight / slight right lanes.
25
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
26
Continue on I 295
0.7 mi·1 min·Throgs Neck Expressway
Use the straight / slight right lanes.
27
Keep slight left at fork onto I 295
6.6 mi·8 min·Cross Bronx Expressway
Use the straight / slight right lanes.
28
Keep slight left at fork onto I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
Toward Upper Level
29
Continue on I 95; US 1
0.6 mi·59 sec·George Washington Bridge (upper level)
30
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
31
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.
32
Keep slight left at fork onto I 95 EXPR; NJTP
0.1 mi·8 sec·I 95 EXPR; NJTP
33
Take the exit
0.2 mi·22 sec
Toward I 95 South, NJTP South: HackensackUse the straight / slight right lanes.
34
Keep slight left at fork
0.4 mi·29 sec
Toward I 95 South, NJTP South: HackensackUse the slight left / slight right lanes.
35
Merge onto I 95; NJTP
2.0 mi·2 min·New Jersey Turnpike
Use the straight / slight right lanes.
36
Take the exit
0.8 mi·1 min
Exit 69Toward I 80 West: Paterson, HackensackUse the straight / slight right lanes.
37
Continue on I 80
68 mi·1 hr 20 min·Christopher Columbus Highway
Use the straight / slight right lanes.
38
Keep slight left at fork onto I 80
5.5 mi·8 min·Keystone Shortway
Use the straight / slight right lanes.
39
Keep slight left at fork onto I 80
12 mi·15 min·Keystone Shortway
40
Take the exit
0.7 mi·46 sec
Exit 293Toward I 380 North: Scranton
41
Continue on I 380
28 mi·30 min·I 380
Use the straight lane.
42
Merge onto I 81
58 mi·1 hr 9 min·I 81
Use the straight lane.
43
Keep slight left at fork onto I 86; NY 17
100 mi·1 hr 56 min·I 86; NY 17
Toward I 86: Corning
44
Keep slight left at fork onto I 390
39 mi·44 min·Genesee Expressway
Toward I 390: Rochester
45
Take the exit
0.4 mi·50 sec
Exit 7Toward NY 408, NY 63: Mount Morris, Letchworth Park
46
Turn right onto NY 408
0.1 mi·10 sec·Mount Morris-Geneseo Road
47
Continue on NY 63
3.3 mi·4 min·Geneseo-Mount Morris Road
48
Turn left onto NY 63
1.3 mi·1 min·Genesee Street
49
Enter roundabout onto NY 63
100 ft·1 sec·Genesee Street
50
Continue on NY 63
7.5 mi·11 min·Genesee Street
51
Continue on NY 63
0.7 mi·54 sec·State Highway 63
52
Continue on NY 63
4.1 mi·6 min·Big Tree Road
53
Continue on NY 63
3.0 mi·4 min·Ellicott Street Road
54
Turn left onto US 20
6.5 mi·8 min·Telephone Road
55
Continue on US 20
8.2 mi·11 min·Broadway Road
56
Arrive at destination
US 20
Trip Plan
Morning Departure
Start early — leave by 6-7 AM to arrive at a reasonable hour.
Evening Departure
This is a long drive — plan for a morning departure or consider splitting it into two days.
This drive is better paced as a 2-day trip.
Plan roughly 2 meaningful breaks for fuel, food, and rest.
The halfway point lands around 199.5 miles from Islip, NY, or about 4h 10m into the drive.
The longest continuous stretch on this route runs about 100 miles.
Consider an overnight stop or starting very early.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 88 miles or 1h 56m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 199.5 miles or 4h 10m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Overnight split
Day 1 wrap after about 199.5 miles or 4h 10m
Stop before fatigue turns the last few hours into a grind. You want day two to start fresh, not just resumed.
Final approach
Final hour starts around 6h 53m
Traffic, exits, and arrival timing usually matter more near Darien, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Islip, 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.
+
Pick one backup stop option before the midpoint in case traffic changes your pacing.
+
Treat this as a 2-day road trip and book the overnight stop before the busiest arrival window.
Day 1
Settle into the route from Islip, NY
Aim for roughly 200 miles and 4.1 hours of wheel time on this day.
Day 2
Finish the approach into Darien, NY
Aim for roughly 200 miles and 4.1 hours of wheel time on this day.
Your first comfortable stop window is around 88 miles from Islip, NY.
This route usually feels better as a 2-day drive than as one long push.
Plan about 2 real breaks rather than only quick fuel stops.
The longest stretch is on I 86 for about 100 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 199.5 mi from Islip, NY
· 4h 10m into the drive
Place data sourced from public business listings. Hours and availability may vary.
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...
6 mi from route
~14 min detour
Free
near mile 55
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...
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...
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...
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...
Station data from NREL Alternative Fuel Stations database.
Driving Electric?
About $42 in charging
· 1 stop
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
119.7
1
$41.89
$19.15
Efficient EV
99.8
1
$34.91
$15.96
EV Truck/SUV
159.6
1
$55.86
$25.54
Gas CO2
140 kg
EV CO2
47 kg (66% less)
Plan for 1 charging stop. A 30-minute DC fast charge mid-route should be enough to complete the trip comfortably.
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 18, 2026
Origin
Islip, NY
Late night
in Islip on Saturday
Local time
3:20 AM
EDT
Current temp
50°F
Scattered Rain Showers then Partly Cloudy
NE 6 mph33% chanceLive forecast
Destination
Darien, NY
Late night
in Darien on Saturday
Local time
3:20 AM
EDT
Current temp
40°F
Unavailable
Live forecast
57°F
Ramapo, NY
200 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.
For long drives, weather on day two can matter just as much as conditions at departure, so check the whole travel window rather than only the first day.
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
10 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
8h 13m on the road
This is long enough that the arrival forecast matters almost as much as departure conditions. Recheck both ends before you roll.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
Frequently Asked Questions
The drive from Islip, NY to Darien, NY covers 399 miles and takes about 8h 13m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are I 86, Christopher Columbus Highway, I 81. Most of the drive stays on highways, so watch for ramps and exits.
Consider an overnight stop or starting very early.
Yes. This route is usually more comfortable as a 2-day drive. A sensible stopping point is after roughly 200 miles on day one.
The midpoint is about 199.5 miles from Islip, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $65.68 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Start early — leave by 6-7 AM to arrive at a reasonable hour. This is a long drive — plan for a morning departure or consider splitting it into two days.
Plan about 2 meaningful breaks for fuel, food, or rest. Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
This is a demanding drive. With 34 significant decision points across 399 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.
The main spots that need attention: at 3.6 miles (CR 57 / Howells Road): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 31.1 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 31.2 miles: Highway fork - watch signs carefully. Lane positioning matters here.
Between Islip, NY and Darien, NY, road signs point toward Cross Island Parkway North, Hempstead Avenue West, Grandstand, Upper Level, Njtp South: Hackensack and Hackensack - among others.
How this page is built
Compiled by the Trip.ovh planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, EIA for fuel prices, NREL for EV charging, and NPS for national parks. See our methodology for refresh cadence and limitations.
