Traveling from Islip to Woodstock covers 143.4 miles and typically takes about 3 hours and 9 minutes of drive time. Because this is a turn-heavy local drive rather than a highway sprint, it functions best as a dedicated day trip. You should budget approximately $23 for fuel to complete the journey. Navigating through the Northeast, you will transition from the coastal environment of Long Island toward the more inland landscape of Woodstock. While it is certainly possible to do this in a single day, the local nature of the roads means you should plan for a full day of travel rather than a quick commute.
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
71.7 miles from Islip, NY
A natural place for your longest stop of the day
, about 1h 39m into the drive
.
Main Roads
Road
Distance
Duration
NY 17
61.2 mi
1h 10m
Southern State Parkway
24.7 mi
31m
NJ 17
14.7 mi
18m
NJ 4
6.7 mi
9m
Cross Bronx Expressway
6.6 mi
8m
State Route 28
5.9 mi
10m
Clearview Expressway
5 mi
5m
Throgs Neck Bridge
2 mi
3m
Longest stretch:
NY 17
— 61.2 mi, about 1h 10m
Turn-by-Turn Driving Directions
Step-by-step road directions between Islip, NY and Woodstock, 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 right at fork
0.2 mi·23 sec
Exit 72AToward NJ 4 West: ParamusUse the slight left / slight right lanes.
35
Merge onto NJ 4
6.7 mi·9 min·NJ 4
Use the slight right lane.
36
Take the exit
0.2 mi·26 sec
Toward GSP South, NJ 17 South, GSP North, NJ 17 North: Grand State Plaza, Newark, MahwahUse the straight lane.
37
Keep slight right at fork
0.2 mi·36 sec
Toward NJ 17 North: MahwahUse the straight / slight right lanes.
38
Merge onto NJ 17
3.3 mi·4 min·NJ 17
Use the straight / slight right lanes.
39
Continue on NJ 17
7.3 mi·9 min·NJ 17
Use the straight / right lanes.
40
Continue on NJ 17
0.7 mi·50 sec·NJ 17
41
Continue on NJ 17
3.3 mi·4 min·NJ 17
42
Continue on I 287; NY 17
0.2 mi·10 sec·I 287; NY 17
43
Keep slight left at fork onto NY 17
61 mi·1 hr 10 min·NY 17
Toward I 87 North, NY 17 North, New York State Thruway North: Albany
44
Take the exit
0.5 mi·1 min
Exit 19Toward NY 28: Kingston, Rhinecliff Bridge
45
Keep slight right at fork
0.1 mi·13 sec
46
Merge onto NY 28
0.5 mi·50 sec·State Route 28
47
Continue on NY 28
5.4 mi·9 min·State Route 28
Use the straight / right lanes.
48
Turn right onto NY 375
1.7 mi·3 min·State Route 375
Use the right lane.
49
Continue on NY 375
1.2 mi·2 min·West Hurley Road
50
At end of road, turn left onto NY 212
0.5 mi·1 min·Mill Hill Road
51
Arrive at destination
NY 212
Trip Plan
Given the 3 hour and 9 minute duration, aim to depart early to avoid the peak congestion often found on local roads. With only one recommended stop, you have the flexibility to pace the trip according to your personal preference, though keeping an eye on your fuel gauge is wise given the $23 estimated cost. Because the entire 143.4-mile path consists of turn-heavy local roads, ensure your GPS is updated and ready to handle frequent directional changes. A helpful tip is to check traffic reports for your specific local roads before leaving Islip, as road construction or local events can significantly impact your travel time on these non-highway routes.
Morning Departure
An early start around 7-8 AM gets you there with plenty of daylight left.
Evening Departure
A late afternoon start means arriving after dark. Morning is better.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 71.7 miles from Islip, NY, or about 1h 39m into the drive.
The longest continuous stretch on this route runs about 61.2 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 32 miles or 45m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 71.7 miles or 1h 39m 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 32m
Traffic, exits, and arrival timing usually matter more near Woodstock, 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.
Day 1
Settle into the route from Islip, NY
This is one driving day of about 143.4 miles and 3h 9m.
Your first comfortable stop window is around 32 miles from Islip, 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 NY 17 for about 61.2 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 31
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
9
50.3 mi into trip|~1h 11m in
Keep slight right at fork toward NJ 4 West: Paramus
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / slight right lanes.
Exit 72A
Toward NJ 4 West: Paramus
Fuel & Cost
Regular Gas
$23.60 one way
$47.21 round trip
$4.18/gal25.4 MPG avg50 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$25.52
$51.05
premium
$4.92
$27.79
$55.59
diesel
$5.61
$31.66
$63.32
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
$24
Tolls
$23
Meals
$25–$50
Total
$71–$96
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 50.2 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $15 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
43
0
$15.06
$6.88
Efficient EV
35.9
0
$12.55
$5.74
EV Truck/SUV
57.4
0
$20.08
$9.18
Gas CO2
50 kg
EV CO2
17 kg (66% 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 15, 2026
Origin
Islip, NY
Afternoon
in Islip on Sunday
Local time
4:22 PM
EDT
Current temp
44°F
Unavailable
Live forecast
Destination
Woodstock, NY
Afternoon
in Woodstock on Sunday
Local time
4:22 PM
EDT
Current temp
51°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
7 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
3h 9m on the road
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
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...
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...
9 mi from route
~21 min detour
Free
near mile 49.5
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...
10 mi from route
~25 min detour
Free
near mile 49.5
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...
10 mi from route
~26 min detour
Free
near mile 49.5
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
~27 min detour
Free
near mile 49.5
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a very different experience than a standard interstate commute, as this route features zero highway driving. You will be navigating a sequence of turn-heavy local roads, relying on routes like Montauk Highway, Main Street, and 3rd Avenue to reach your destination. Since the entire journey is comprised of local streets, your pace will be dictated by traffic and intersections rather than high-speed cruising. Be prepared for a continuous, hands-on driving experience where your focus remains on local navigation rather than long, uninterrupted stretches of pavement. This route is defined by its intimacy with the local road network.
91% highway — fuel and pacing are the main things to plan.
51 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 61.2 mi on NY 17.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on NY 17 and Southern State Parkway. 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 31 significant decision points across 143.4 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.
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 Woodstock, NY, road signs point toward Cross Island Parkway North, Hempstead Avenue West, Grandstand, Upper Level, Njtp South: Hackensack and Gsp South - 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 3h 9m. Total distance: 143.4 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
3h 9m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (91%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 61.2 miles on NY 17. 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 Woodstock, 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 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 — 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.
Possible but tiring. At 3.2 hours each way, an in-and-out day trip would put you behind the wheel for 6.3 hours — manageable with a long break at Woodstock, NY, but most travelers stay overnight.
