Embarking on the 303.9-mile journey from Islip to Lenox is a manageable trek that typically takes about 6 hours and 15 minutes of drive time. Because this route stays entirely within New York, you will transition from the suburban Northeast coast toward inland areas without crossing state lines. Budgeting approximately $49 for fuel is a smart move before you head out. While the drive is feasible as a single-day trip, be prepared for a full day behind the wheel. It is an ideal route for those comfortable with a mix of parkway driving and local navigation, provided you keep an eye on your timing.
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
1 planned break
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
151.9 miles from Islip, NY
A natural place for your longest stop of the day
, about 3h 12m into the drive
.
Main Roads
Road
Distance
Duration
NY 17
117.5 mi
2h 15m
New York State Thruway
105 mi
2h 1m
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
Clearview Expressway
5 mi
5m
NY 365A
3.5 mi
7m
Longest stretch:
NY 17
— 117.5 mi, about 2h 15m
Turn-by-Turn Driving Directions
Step-by-step road directions between Islip, NY and Lenox, 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
118 mi·2 hr 15 min·NY 17
Toward I 87 North, NY 17 North, New York State Thruway North: AlbanyUse the straight / slight right lanes.
44
Keep slight left at fork onto I 90
105 mi·2 hr 1 min·New York State Thruway
Toward I 90 West: Buffalo
45
Take the exit
1.1 mi·2 min
Exit 33Toward NY 365: Verona, OneidaUse the slight right lane.
46
At end of road, turn left onto NY 365
2.9 mi·4 min·NY 365
47
Turn right onto NY 365A
3.5 mi·7 min·NY 365A
Use the right lane.
48
Continue on CR 97
1.2 mi·2 min·Upper Lenox Avenue
49
Turn slight left onto CR 29
129 ft·3 sec·Creek Road
50
Keep slight right at fork onto CR 97
0.2 mi·40 sec·Upper Lenox Avenue
51
Turn sharp right onto CR 54
268 ft·7 sec·South Court Street
52
Arrive at destination
CR 54
Trip Plan
To keep your 6 hour and 15 minute journey smooth, plan to depart early in the morning to avoid the heaviest regional traffic. Since the route includes one recommended stop, use that break strategically to stretch your legs and refuel after your longest highway segments. Keep in mind that the turn-heavy nature of the local roads requires more active focus than a standard interstate cruise, so pace yourself accordingly. Given the 303.9-mile distance, having a flexible schedule is a major advantage. If you find the winding local sections tiring, prioritize your main stop toward the latter half of the trip to recharge before finishing your arrival in Lenox.
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 1 meaningful break for fuel, food, and rest.
The halfway point lands around 151.9 miles from Islip, NY, or about 3h 12m into the drive.
The longest continuous stretch on this route runs about 117.5 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 67 miles or 1h 33m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 151.9 miles or 3h 12m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 5h 4m
Traffic, exits, and arrival timing usually matter more near Lenox, 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 303.9 miles and 6h 15m.
Your first comfortable stop window is around 67 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 117.5 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 32
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
$50.02 one way
$100.05 round trip
$4.18/gal25.4 MPG avg106 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$54.09
$108.18
premium
$4.92
$58.90
$117.80
diesel
$5.61
$67.10
$134.19
Estimated Tolls: $27.80
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
New York State Thruway
(105 mi)$5.25
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
$50
Tolls
$28
Meals
$25–$50
Total
$103–$128
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 106.3 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $32 in charging
· 1 stop
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
91.2
1
$31.91
$14.59
Efficient EV
76
0
$26.59
$12.16
EV Truck/SUV
121.6
1
$42.55
$19.45
Gas CO2
106 kg
EV CO2
36 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 13, 2026
Origin
Islip, NY
Morning
in Islip on Tuesday
Local time
6:25 AM
EDT
Current temp
54°F
Slight Chance Rain Showers then Areas Of Fog
SW 5 to 14 mph15% chanceLive forecast
Flood Warning
Flood Warning issued April 13 at 11:26AM EDT until April 15 at 8:00AM EDT by NWS Binghamton NY
Destination
Lenox, NY
Morning
in Lenox on Tuesday
Local time
6:25 AM
EDT
Current temp
45°F
Unavailable
Live forecast
63°F
Ramapo, NY
152 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
9 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
6h 15m 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
~13 min detour
Free
near mile 52.4
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...
5 mi from route
~13 min detour
Free
near mile 52.4
For centuries, the Oneida Carrying Place, a six-mile portage connecting the Mohawk River and Wood Creek, served as a vital link for those traveling by water from the ocean to the Great Lakes. When Eur...
7 mi from route
~18 min detour
Free
near mile 293.4
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
~26 min detour
Free
near mile 52.4
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...
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...
12 mi from route
~30 min detour
Free
near mile 52.4
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a diverse experience behind the wheel, as this route is characterized by a turn-heavy local profile that keeps you engaged. You will spend about 60% of your time on highways, utilizing a combination of the Southern State Parkway, NY 17, and the New York State Thruway. The longest uninterrupted stretch covers 117.5 miles along NY 17, offering a significant portion of the drive where you can settle into a steady rhythm. As you move away from the coast, the road’s personality shifts from dense suburban corridors to more technical, winding local segments. This variation ensures the drive feels dynamic rather than monotonous.
60% highway — fuel and pacing are the main things to plan.
52 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 117.5 mi on NY 17.
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 32 significant decision points across 303.9 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 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
Gently rolling terrain
577 ft12 ft
Total Climb
1,620 ft
Total Descent
1,093 ft
Highest Point
577 ft
~291.2 mi in
Elevation Range
565 ft
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 Lenox, 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 6h 15m. Total distance: 303.9 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
6h 15m drive, plan rest stops for pacing.
Frequently Asked Questions
The longest stretch is about 117.5 miles on NY 17. The full list of main roads is in the Roads section above.
Expect about $27.80 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 Lenox, 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 Fort Stanwix 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 6.3 hours each way, a round trip means 12.5 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Lenox, NY before the return drive.
