Darien, NY to Islip, NY is 398.3 miles and takes about 8h 12m via Southern Tier Expressway, Keystone Shortway, and I 81, with a fuel budget near $66 and best split over 2 days. This journey primarily traverses New York State, moving from the Western part towards Long Island. It's a practical route for those prioritizing efficiency, with a significant portion on major expressways. Consider this trip if you need a straightforward connection across the state, with a clear plan for overnighting rather than attempting it all in one go.
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
199.2 miles from Darien, NY
A natural place for your longest stop of the day
, about 4h 3m 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 highway-focused drive, with 67% of the route utilizing major roadways like the Southern Tier Expressway and I 81. Expect mostly fast-paced travel, though the Keystone Shortway may offer a slight change of pace. The longest continuous stretch you'll encounter is 104.5 miles on the Southern Tier Expressway, so plan your breaks accordingly. The road character remains consistently geared towards efficient travel for most of the 8h 12m journey.
Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 58 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Southern Tier Expressway is the longest continuous segment at about 104.5 miles.
How Hard Is This Drive?
This is a straightforward highway drive that stays mostly on Southern Tier Expressway and Keystone Shortway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 231.3 miles in near US 6.
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 398.3 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 231.3 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 345.8 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 346.1 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
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
231.3 mi into trip|~4h 41m 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
345.8 mi into trip|~6h 57m 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
346.1 mi into trip|~6h 57m 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
355.5 mi into trip|~7h 11m 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
9
393.7 mi into trip|~8h 3m in
Take the exit toward Bay Shore Road South, Bay Shore
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 41S
Toward Bay Shore Road South, Bay Shore
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Darien, NY and Islip, NY, road signs point toward Mt Pocono, Milford, New York City, Leonia, Teaneck and George Washington Bridge Upper Level - among others.
Step-by-step road directions between Darien, NY and Islip, NY.
1
Start on US 20
8.2 mi·11 min·Broadway Road
2
Continue on US 20
6.5 mi·8 min·Telephone Road
3
Turn right onto NY 63
3.0 mi·4 min·Ellicott Street Road
4
Continue on NY 63
4.1 mi·6 min·Big Tree Road
5
Continue on NY 63
0.7 mi·54 sec·State Highway 63
6
Continue on NY 63
7.5 mi·11 min·Genesee Street
7
Enter roundabout onto NY 63
108 ft·1 sec·Genesee Street
8
Continue on NY 63
1.3 mi·1 min·Genesee Street
9
Merge onto US 20A; NY 39; NY 63
3.3 mi·4 min·Geneseo-Mount Morris Road
10
Continue on NY 408
0.3 mi·32 sec·Mount Morris-Geneseo Road
11
Take the ramp
0.4 mi·53 sec
12
Merge onto I 390
38 mi·44 min·Genesee Expressway
13
Merge onto I 86
105 mi·2 hr 2 min·Southern Tier Expressway
14
Keep slight right at fork onto I 81
53 mi·1 hr 3 min·I 81
Toward I 81 South: ScrantonUse the straight lane.
15
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.
16
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.
17
Keep slight right at fork onto I 380
24 mi·25 min·I 380
Exit 4Toward I 380 South: Mount Pocono
18
Keep slight left at fork
1.0 mi·1 min
Exit 1BToward I 80 East: Stroudsburg
19
Merge onto I 80
80 mi·1 hr 37 min·Keystone Shortway
Use the straight / right lanes.
20
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.
21
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.
22
Keep slight right at fork
0.4 mi·38 sec
Exit 70A-BToward Leonia, TeaneckUse the slight right lane.
23
Turn right
0.2 mi·35 sec
Exit 70AToward LeoniaUse the straight / slight right lanes.
24
Turn straight onto CR 56
454 ft·9 sec·Degraw Avenue
25
Continue on CR 56
1.1 mi·2 min·Fort Lee Road
Use the straight / right lanes.
26
Continue on CR 56
469 ft·13 sec·Main Street
27
Take the ramp
472 ft·12 sec
Toward George Washington Bridge
28
Merge onto US 1; US 9; US 46
0.3 mi·28 sec·Bergen Boulevard
Use the straight / slight right lanes.
29
Take the exit
312 ft·4 sec
Toward George Washington Bridge Upper Level
30
Merge onto I 95 EXPR
0.3 mi·20 sec·I 95 EXPR
Use the straight / slight right lanes.
31
Keep slight left at fork onto I 95 EXPR
0.8 mi·1 min·I 95 EXPR
32
Continue on I 95; US 1; US 9
0.6 mi·1 min·George Washington Bridge (upper level)
Use the straight / slight right lanes.
33
Continue on I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
34
Continue on I 95; US 1
4.7 mi·6 min·Cross Bronx Expressway
Use the straight / slight right lanes.
35
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.
36
Merge onto I 295
0.6 mi·58 sec·Throgs Neck Expressway
37
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
Use the straight / slight right lanes.
38
Continue on I 295
5.0 mi·5 min·Clearview Expressway
Use the straight / slight right lanes.
39
Continue on NY 24
0.7 mi·1 min·Hollis Court Boulevard
Use the straight lane.
40
At end of road, turn left onto NY 24
0.2 mi·35 sec·Jamaica Avenue
Use the left lane.
41
Turn right onto Hempstead Avenue
0.9 mi·2 min·Hempstead Avenue
42
Turn right onto 225th Street
228 ft·9 sec·225th Street
Use the right lane.
43
Take the ramp
0.2 mi·28 sec
Toward Cross Island Parkway South, Verrazano Bridge
44
Merge onto CI
1.3 mi·1 min·Cross Island Parkway
Use the straight / slight right lanes.
45
Take the exit
0.5 mi·1 min
Exit 25AToward Southern State Parkway East, Eastern Long IslandUse the slight left / straight lanes.
46
Merge onto SO
25 mi·31 min·Southern State Parkway
Use the straight / slight right lanes.
47
Keep slight left at fork onto SO
0.2 mi·16 sec·Southern State Parkway
Use the straight / slight right lanes.
48
Take the exit
0.2 mi·31 sec
Exit 41SToward Bay Shore Road South, Bay ShoreUse the slight right lane.
49
Turn straight onto CR 57
0.5 mi·1 min·Bay Shore Road
50
Continue on CR 57
0.3 mi·43 sec·Howells Road
51
Turn straight onto CR 57
341 ft·6 sec·Sunrise Highway
52
Keep slight right at fork onto CR 57
0.6 mi·1 min·Howells Road
Toward Howells Road SouthUse the right lane.
53
Continue on CR 57
0.2 mi·24 sec·Roosevelt Street
54
Continue on CR 57
0.7 mi·1 min·3rd Avenue
55
At end of road, turn left onto NY 27A
1.1 mi·1 min·East Main Street
56
Continue on Montauk Highway
0.2 mi·17 sec·Montauk Highway
57
Continue on NY 27A
0.8 mi·1 min·Main Street
58
Arrive at destination
NY 27A
Trip Plan
Given the 8h 12m duration, splitting this trip over 2 days is highly recommended to avoid fatigue. Aim to leave Darien in the morning to make good progress before stopping for the night. With 2 planned stops, you'll have opportunities to refuel and rest. Keep an eye on your fuel levels, especially before longer stretches like the 104.5 miles on the Southern Tier Expressway, as services can sometimes be spread out on these major routes. A good midpoint for an overnight stay would put you roughly halfway through your journey.
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 199.2 miles from Darien, NY, or about 4h 3m into the drive.
The longest continuous stretch on this route runs about 104.5 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 52m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 199.2 miles or 4h 3m 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 199.2 miles or 4h 3m
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 48m
Traffic, exits, and arrival timing usually matter more near Islip, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Darien, 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 Darien, NY
Aim for roughly 199 miles and 4.1 hours of wheel time on this day.
Day 2
Finish the approach into Islip, NY
Aim for roughly 199 miles and 4.1 hours of wheel time on this day.
Your first comfortable stop window is around 88 miles from Darien, 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 Southern Tier Expressway for about 104.5 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 199.2 mi from Darien, NY
· 4h 3m 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
~16 min detour
Free
near mile 343.4
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...
7 mi from route
~17 min detour
Free
near mile 357.1
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...
10 mi from route
~25 min detour
Free
near mile 343.4
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...
11 mi from route
~28 min detour
Free
near mile 343.4
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...
11 mi from route
~28 min detour
Free
near mile 398.3
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...
12 mi from route
~30 min detour
Free
near mile 343.4
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
119.5
1
$41.82
$19.12
Efficient EV
99.6
1
$34.85
$15.93
EV Truck/SUV
159.3
1
$55.76
$25.49
Gas CO2
139 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 17, 2026
Origin
Darien, NY
Evening
in Darien on Friday
Local time
7:12 PM
EDT
Current temp
63°F
Partly Sunny
NE 5 mph0% chanceLive forecast
Destination
Islip, NY
Evening
in Islip on Friday
Local time
7:12 PM
EDT
Current temp
44°F
Unavailable
Live forecast
57°F
Ramapo, NY
199 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
19 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 12m 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 Darien, NY to Islip, NY covers 398.3 miles and takes about 8h 12m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Southern Tier Expressway, Keystone Shortway, 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 199 miles on day one.
The midpoint is about 199.2 miles from Darien, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $65.56 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 398.3 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 231.3 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 345.8 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 346.1 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Between Darien, NY and Islip, NY, road signs point toward Mt Pocono, Milford, New York City, Leonia, Teaneck and George Washington Bridge Upper Level - 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.
