This 383.9-mile journey from Caledonia, NY, to Islip, NY, is designed for a single day, taking approximately 7 hours and 53 minutes of driving time. You'll be spending about 69% of your time on highways, making it a predominantly highway-focused drive. With an estimated fuel cost of $63, this route is an efficient option for traversing the Northeast region. The drive is structured with two recommended stops, and the longest continuous stretch you'll encounter is 104.5 miles along the Southern Tier Expressway. This is a straightforward trip that can be completed comfortably in one day.
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
2 planned breaks
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
192 miles from Caledonia, NY
A natural place for your longest stop of the day
, about 3h 52m into the drive
.
Step-by-step road directions between Caledonia, NY and Islip, NY.
1
Start on NY 5; NY 36
247 ft·6 sec·NY 5; NY 36
2
Continue on NY 5
0.7 mi·1 min·State Street
3
Continue on NY 5
5.7 mi·8 min·Caledonia-Avon Road
4
Continue on US 20; NY 5
0.5 mi·32 sec·West Main Street
5
Turn right onto NY 39
1.0 mi·1 min·Wadsworth Avenue
6
Continue on NY 39
3.3 mi·4 min·Avon-Geneseo Road
7
Continue on NY 39
4.5 mi·7 min·Avon Road
8
Continue on NY 39
0.3 mi·41 sec·Main Street
9
Enter roundabout onto NY 39
67 ft·2 sec·Main Street
10
Continue on NY 39
0.2 mi·29 sec·Main Street
11
At end of road, turn right onto US 20A; NY 39
497 ft·14 sec·South Street
12
Continue on US 20A; NY 39
0.6 mi·1 min·Mount Morris Road
13
Continue on US 20A; NY 39; NY 63
3.3 mi·4 min·Geneseo-Mount Morris Road
14
Continue on NY 408
0.3 mi·32 sec·Mount Morris-Geneseo Road
15
Take the ramp
0.4 mi·53 sec
16
Merge onto I 390
38 mi·44 min·Genesee Expressway
17
Merge onto I 86
105 mi·2 hr 2 min·Southern Tier Expressway
18
Keep slight right at fork onto I 81
53 mi·1 hr 3 min·I 81
Toward I 81 South: ScrantonUse the straight lane.
19
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.
20
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.
21
Keep slight right at fork onto I 380
24 mi·25 min·I 380
Exit 4Toward I 380 South: Mount Pocono
22
Keep slight left at fork
1.0 mi·1 min
Exit 1BToward I 80 East: Stroudsburg
23
Merge onto I 80
80 mi·1 hr 37 min·Keystone Shortway
Use the straight / right lanes.
24
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.
25
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.
26
Keep slight right at fork
0.4 mi·38 sec
Exit 70A-BToward Leonia, TeaneckUse the slight right lane.
27
Turn right
0.2 mi·35 sec
Exit 70AToward LeoniaUse the straight / slight right lanes.
28
Turn straight onto CR 56
454 ft·9 sec·Degraw Avenue
29
Continue on CR 56
1.1 mi·2 min·Fort Lee Road
Use the straight / right lanes.
30
Continue on CR 56
469 ft·13 sec·Main Street
31
Take the ramp
472 ft·12 sec
Toward George Washington Bridge
32
Merge onto US 1; US 9; US 46
0.3 mi·28 sec·Bergen Boulevard
Use the straight / slight right lanes.
33
Take the exit
312 ft·4 sec
Toward George Washington Bridge Upper Level
34
Merge onto I 95 EXPR
0.3 mi·20 sec·I 95 EXPR
Use the straight / slight right lanes.
35
Keep slight left at fork onto I 95 EXPR
0.8 mi·1 min·I 95 EXPR
36
Continue on I 95; US 1; US 9
0.6 mi·1 min·George Washington Bridge (upper level)
Use the straight / slight right lanes.
37
Continue on I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
38
Continue on I 95; US 1
4.7 mi·6 min·Cross Bronx Expressway
Use the straight / slight right lanes.
39
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.
40
Merge onto I 295
0.6 mi·58 sec·Throgs Neck Expressway
41
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
Use the straight / slight right lanes.
42
Continue on I 295
5.0 mi·5 min·Clearview Expressway
Use the straight / slight right lanes.
43
Continue on NY 24
0.7 mi·1 min·Hollis Court Boulevard
Use the straight lane.
44
At end of road, turn left onto NY 24
0.2 mi·35 sec·Jamaica Avenue
Use the left lane.
45
Turn right onto Hempstead Avenue
0.9 mi·2 min·Hempstead Avenue
46
Turn right onto 225th Street
228 ft·9 sec·225th Street
Use the right lane.
47
Take the ramp
0.2 mi·28 sec
Toward Cross Island Parkway South, Verrazano Bridge
48
Merge onto CI
1.3 mi·1 min·Cross Island Parkway
Use the straight / slight right lanes.
49
Take the exit
0.5 mi·1 min
Exit 25AToward Southern State Parkway East, Eastern Long IslandUse the slight left / straight lanes.
50
Merge onto SO
25 mi·31 min·Southern State Parkway
Use the straight / slight right lanes.
51
Keep slight left at fork onto SO
0.2 mi·16 sec·Southern State Parkway
Use the straight / slight right lanes.
52
Take the exit
0.2 mi·31 sec
Exit 41SToward Bay Shore Road South, Bay ShoreUse the slight right lane.
53
Turn straight onto CR 57
0.5 mi·1 min·Bay Shore Road
54
Continue on CR 57
0.3 mi·43 sec·Howells Road
55
Turn straight onto CR 57
341 ft·6 sec·Sunrise Highway
56
Keep slight right at fork onto CR 57
0.6 mi·1 min·Howells Road
Toward Howells Road SouthUse the right lane.
57
Continue on CR 57
0.2 mi·24 sec·Roosevelt Street
58
Continue on CR 57
0.7 mi·1 min·3rd Avenue
59
At end of road, turn left onto NY 27A
1.1 mi·1 min·East Main Street
60
Continue on Montauk Highway
0.2 mi·17 sec·Montauk Highway
61
Continue on NY 27A
0.8 mi·1 min·Main Street
62
Arrive at destination
NY 27A
Trip Plan
To make the most of this 383.9-mile trip, consider an early morning departure from Caledonia, NY, to maximize daylight and minimize traffic. With a total driving time of nearly 8 hours, planning for two stops is wise; perhaps one around the halfway point to stretch your legs and grab a bite. Keep an eye on your fuel gauge, especially before entering longer stretches like the 104.5 miles on the Southern Tier Expressway, as services can sometimes be spaced out on major highways. The $63 fuel cost is a good estimate, but it's always prudent to budget a little extra.
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.
You can normally do this drive in one day.
Plan roughly 2 meaningful breaks for fuel, food, and rest.
The halfway point lands around 192 miles from Caledonia, NY, or about 3h 52m into the drive.
The longest continuous stretch on this route runs about 104.5 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 84 miles or 1h 45m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 192 miles or 3h 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 6h 29m
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 Caledonia, 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.
Day 1
Settle into the route from Caledonia, NY
This is one driving day of about 383.9 miles and 7h 53m.
Your first comfortable stop window is around 84 miles from Caledonia, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
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.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 35
5 decision points cluster between mile 216.9 and 379.3 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
9
216.9 mi into trip|~4h 21m 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
331.4 mi into trip|~6h 37m 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
331.7 mi into trip|~6h 38m 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
341.1 mi into trip|~6h 52m 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
379.3 mi into trip|~7h 44m 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
Fuel & Cost
Regular Gas
$63.19 one way
$126.38 round trip
$4.18/gal25.4 MPG avg134 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$68.33
$136.66
premium
$4.92
$74.41
$148.81
diesel
$5.61
$84.76
$169.52
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
$63
Tolls
$23
Meals
$25–$50
Total
$111–$136
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 134.3 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $40 in charging
· 1 stop
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
115.2
1
$40.31
$18.43
Efficient EV
96
1
$33.59
$15.36
EV Truck/SUV
153.6
1
$53.75
$24.57
Gas CO2
134 kg
EV CO2
45 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 15, 2026
Origin
Caledonia, NY
Late night
in Caledonia on Monday
Local time
2:11 AM
EDT
Current temp
41°F
Unavailable
Live forecast
Destination
Islip, NY
Late night
in Islip on Monday
Local time
2:11 AM
EDT
Current temp
44°F
Unavailable
Live forecast
63°F
Ramapo, NY
192 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
3 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
7h 53m on the road
Start early — leave by 6-7 AM to arrive at a reasonable hour.
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...
5 mi from route
~12 min detour
Free
near mile 330.6
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...
5 mi from route
~13 min detour
Free
near mile 330.6
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...
9 mi from route
~23 min detour
Free
near mile 330.6
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
~26 min detour
Free
near mile 330.6
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 330.6
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
~28 min detour
Free
near mile 330.6
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
The character of this drive is largely defined by its highway focus, with a significant 69% of the route utilizing major expressways. You'll experience long stretches of consistent speed, particularly the 104.5-mile segment on the Southern Tier Expressway. While the Keystone Shortway and I-81 also contribute to the highway nature, expect a steady pace for most of the 7-hour journey. This route prioritizes efficient travel over varied road types, offering a predictable driving experience for those looking to cover distance quickly.
69% highway — fuel and pacing are the main things to plan.
62 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 104.5 mi on Southern Tier Expressway.
How Hard Is This Drive?
10/10
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 216.9 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 35 significant decision points across 383.9 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 216.9 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 331.4 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 331.7 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 Caledonia, NY and Islip, NY, road signs point toward Mt Pocono, Milford, New York City, Leonia, Teaneck and George Washington Bridge Upper Level - among others.
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
Doable as a same-day drive at 7h 53m. Total distance: 383.9 miles.
Family Friendly
Moderate complexity with 2 natural rest stops along the way.
Solo Traveler
7h 53m drive, plan rest stops for pacing.
Frequently Asked Questions
The longest stretch is about 104.5 miles on Southern Tier Expressway. 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 Islip, 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 2 meaningful breaks. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 216.9 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 331.4 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 331.7 miles: Highway fork - watch signs carefully. 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.
Not recommended in a single day. At 7.9 hours each way, a round trip means 15.8 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Islip, NY before the return drive.
