Islip, NY to Pleasantville, NY is 431.6 miles and takes about 9h 14m via Keystone Shortway, Christopher Columbus Highway, and Southern State Parkway, with a fuel budget near $72 and enough daylight to finish in a day. This trip stays within New York, traversing the Northeast region. With a recommended 2 days for the drive, you'll encounter a route that primarily uses surface roads, suggesting a more local travel experience rather than a high-speed interstate run. Consider this option if you prefer a less highway-intensive experience and have the time to break up the drive.
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
215.8 miles from Islip, NY
A natural place for your longest stop of the day
, about 4h 22m into the drive
.
Main Roads
Road
Distance
Duration
Keystone Shortway
200 mi
3h 44m
Christopher Columbus Highway
68.2 mi
1h 20m
Southern State Parkway
24.7 mi
31m
Market Street
15.6 mi
19m
US 219
12.3 mi
18m
Montmorenci Road
8.8 mi
13m
PA 948
8.6 mi
12m
State Park Road
7.5 mi
13m
Longest stretch:
Keystone Shortway
— 200 mi, about 3h 44m
Traffic on I-80
Hour-of-day weekday pattern from 194 FHWA count stations on your route.
Peak
3 PM
~3,076 veh/hr typical
· worst 3,665
Quietest
1 AM
~346 veh/hr
Peak-to-quiet ratio
8.9×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 52 weeks of 2023 FHWA Travel Monitoring Analysis System data. Weekday hours only (Mon–Fri).
Turn-by-Turn Driving Directions
Step-by-step road directions between Islip, NY and Pleasantville, 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
195 mi·3 hr 35 min·Keystone Shortway
40
Take the exit
0.5 mi·1 min
Toward PA 153: Clearfield, Penfield
41
Keep slight right at fork
0.2 mi·32 sec
42
Turn straight onto PA 153
7.5 mi·13 min·State Park Road
43
Continue on PA 153
5.0 mi·8 min·Hoovertown Road
44
Continue on PA 153
3.7 mi·6 min·Penfield Road
45
At end of road, turn right onto US 219
12 mi·18 min·US 219
46
Turn right onto PA 948
1.0 mi·2 min·Montmorenci Avenue
47
Continue on PA 948
8.8 mi·13 min·Montmorenci Road
48
Continue on PA 948
5.4 mi·7 min·Highland Road
49
At end of road, turn left onto PA 66
2.7 mi·3 min·Kane-Russell City Road
50
Take the exit onto PA 948
8.6 mi·12 min·PA 948
51
Continue on PA 666
2.3 mi·4 min·PA 666
52
At end of road, turn left onto US 6
1.2 mi·2 min·West Main Street
53
Continue on US 6
4.5 mi·6 min·Grand Army of the Republic Highway
54
Continue on US 6
1.4 mi·2 min·South Main Street
55
Continue on US 6
2.9 mi·4 min·Grand Army of the Republic Highway
56
Continue on US 6
0.2 mi·35 sec·Main Street
57
Continue on US 6
1.8 mi·3 min·Crescent Park
Use the straight lane.
58
Continue on Crescent Park
0.4 mi·1 min·Crescent Park
Use the right lane.
59
Turn right onto Hickory Bridge
0.1 mi·17 sec·Hickory Bridge
Use the right lane.
60
Continue on Hickory Street
0.2 mi·25 sec·Hickory Street
Use the straight / left lanes.
61
Turn right onto US 62
0.2 mi·23 sec·West 4th Avenue
62
Turn left onto US 62
16 mi·19 min·Market Street
63
At end of road, turn left onto NY 60
0.2 mi·15 sec·Foote Avenue
64
Turn right onto Martin Road
2.1 mi·3 min·Martin Road
65
Turn right onto Glenview Avenue
0.1 mi·22 sec·Glenview Avenue
66
Turn left onto West Virginia Boulevard
0.4 mi·53 sec·West Virginia Boulevard
67
Continue on Maple Street
0.4 mi·51 sec·Maple Street
68
Continue on Allen Street
0.2 mi·29 sec·Allen Street
69
Turn left onto Winsor Street
161 ft·5 sec·Winsor Street
70
Continue on this road
0.1 mi·22 sec·this road
71
Continue on Winsor Street Bridge
0.8 mi·2 min·Winsor Street Bridge
72
At end of road, turn left onto Newton Avenue
73 ft·5 sec·Newton Avenue
73
Turn right onto Lakeview Avenue
0.8 mi·1 min·Lakeview Avenue
74
Turn left onto Marvin Parkway
0.2 mi·28 sec·Marvin Parkway
75
Turn right onto NY 60
283 ft·6 sec·North Main Street
76
Keep slight left at fork onto NY 60
0.2 mi·21 sec·North Main Street
77
Keep slight right at fork onto NY 60
0.5 mi·56 sec·North Main Street
78
Merge onto I 86; NY 17
7.1 mi·8 min·Southern Tier Expressway
79
Take the exit
1.3 mi·2 min
Exit 10Toward Bemus Point
80
Turn slight right
0.2 mi·22 sec
Exit 10Toward Bemus Point, Ellery Center
81
Turn right onto Bemus-Ellery Road
467 ft·18 sec·Bemus-Ellery Road
82
Turn left onto Bayview Road
5.1 mi·8 min·Bayview Road
83
Keep slight right at fork onto Bayview Road
1.6 mi·2 min·Bayview Road
84
Turn left onto Centralia-Hartfield Road
1.7 mi·4 min·Centralia-Hartfield Road
85
Arrive at destination
Centralia-Hartfield Road
Trip Plan
Given the 9h 14m estimated drive time, breaking this trip into two days is highly recommended. Aim to leave early in the morning to maximize daylight, especially if you plan to stop frequently. With 2 recommended days, you can comfortably cover around 215 miles per day. Plan your fuel stops strategically, as the total fuel cost is estimated at $72; topping off before longer stretches on the Keystone Shortway is a good idea. Look for rest areas or towns with amenities after approximately 100-120 miles each day to stretch your legs.
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 215.8 miles from Islip, NY, or about 4h 22m into the drive.
The longest continuous stretch on this route runs about 200 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 95 miles or 2h 4m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 215.8 miles or 4h 22m 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 215.8 miles or 4h 22m
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 7h 40m
Traffic, exits, and arrival timing usually matter more near Pleasantville, 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 216 miles and 4.6 hours of wheel time on this day.
Day 2
Finish the approach into Pleasantville, NY
Aim for roughly 216 miles and 4.6 hours of wheel time on this day.
Your first comfortable stop window is around 95 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 Keystone Shortway for about 200 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 55
5 decision points cluster between mile 3.6 and 50.3 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
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
Fuel & Cost
Regular Gas
$76.60 one way
$153.20 round trip
$4.51/gal25.4 MPG avg151 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.85
$82.34
$164.69
premium
$5.24
$89.02
$178.04
diesel
$5.35
$90.91
$181.82
Estimated Tolls: $22.83
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
New Jersey Turnpike
(2 mi)$0.28
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
$77
Tolls
$23
Hotel (1n)
$80–$140
Meals
$50–$100
Total
$229–$339
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 151 kg one way.
Prices: EIA weekly data, 2026-06-01.
Driving Electric?
About $45 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
129.5
1
$45.32
$20.72
Efficient EV
107.9
1
$37.77
$17.26
EV Truck/SUV
172.6
2
$60.42
$27.62
Gas CO2
151 kg
EV CO2
50 kg (67% 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 Jun 1, 2026
Origin
Islip, NY
Afternoon
in Islip on Wednesday
Local time
3:06 PM
EDT
Current temp
50°F
Mostly Clear
NE 2 to 10 mph0% chanceLive forecast
Destination
Pleasantville, NY
Afternoon
in Pleasantville on Wednesday
Local time
3:06 PM
EDT
Current temp
47°F
Clear
NE 3 to 12 mph0% chanceLive 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.
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
3 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
9h 14m 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.
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...
4 mi from route
~10 min detour
Free
near mile 44.6
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 44.6
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...
10 mi from route
~24 min detour
Free
near mile 44.6
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
~27 min detour
Free
near mile 44.6
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 44.6
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...
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This route is mostly surface roads, with only 17% of the travel on highways. You'll experience a longest stretch of 200 miles on the Keystone Shortway before transitioning to surface roads. Expect frequent exits and intersections as you navigate through populated areas and local communities, which is typical for a route with a high surface road share.
Only 17% highway — the rest is turn-by-turn surface driving.
85 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 200 mi on Keystone Shortway.
How Hard Is This Drive?
10/10
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. 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 55 significant decision points across 431.6 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 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.
Elevation Profile
Hilly terrain with moderate elevation changes
1,797 ft12 ft
Total Climb
3,587 ft
Total Descent
2,191 ft
Highest Point
1,797 ft
~369.9 mi in
Elevation Range
1,785 ft
Notable High Points
1,737 ft at ~154.1 miles+871 ft prominence
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 Pleasantville, NY, road signs point toward Cross Island Parkway North, Hempstead Avenue West, Grandstand, Upper Level, Njtp South: Hackensack and Hackensack - 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
Pleasantville is a village in Westchester County, New York. Downtown Pleasantville is very walkable, and has many independent restaurants, boutique shops, and grocery stores. The Jacob Burns Film Center, in the Rome Theater in downtown, was one of the first movie theaters in Westchester, and focuses primarily on independent, documentary, and world cinema.
Mostly surface roads route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 200 miles on Keystone Shortway. The full list of main roads is in the Roads section above.
Yes — a 2-day pace is more comfortable than one long haul. A sensible stopping point is after roughly 216 miles on day one.
Expect about $22.83 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.
Yes — we found about 36 rest areas or service plazas within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
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 Pleasantville, 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. There are 36 rest areas along the route for bathroom stops.
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.
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 9.2 hours each way, a round trip means 18.5 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Pleasantville, NY before the return drive.
