Islip to Chappaqua is 69 miles and takes about 1 hour 40 minutes via Southern State Parkway and Hutchinson River Parkway, with a fuel budget near $13 and enough daylight to finish in a day. This trip stays within New York, taking you from the Northeast region to another part of the Northeast. It's a relatively short drive, mostly on parkways, making it a convenient option for a quick trip without extensive planning. You'll spend most of your time on well-maintained parkways, which generally offer a smoother driving experience than standard highways.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
34.5 miles from Islip, NY
A natural place for your longest stop of the day
, about 49m into the drive
.
Main Roads
Road
Distance
Duration
Southern State Parkway
24.7 mi
31m
Hutchinson River Parkway
13.5 mi
19m
King Street
5.8 mi
10m
Clearview Expressway
5 mi
5m
I 684
3 mi
3m
Throgs Neck Expressway
2.5 mi
3m
Throgs Neck Bridge
2 mi
3m
Main Street
1.8 mi
3m
Longest stretch:
Southern State Parkway
— 24.7 mi, about 31m
Traffic on I-295
Hour-of-day weekday pattern from 11 FHWA count stations on your route.
Peak
4 PM
~1,766 veh/hr typical
· worst 2,167
Quietest
2 AM
~199 veh/hr
Peak-to-quiet ratio
8.9×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 48 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 Chappaqua, 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 right at fork onto I 695
1.8 mi·2 min·Throgs Neck Expressway
Exit 10Toward I 695 North: New HavenUse the straight / slight right lanes.
28
Merge onto I 95
1.0 mi·1 min·Bruckner Expressway
29
Continue on I 95
0.2 mi·18 sec·New England Thruway
30
Take the exit
430 ft·14 sec
Exit 9Toward Hutchinson Parkway NorthUse the slight right lane.
31
Keep slight left at fork
0.2 mi·31 sec
Toward Hutchinson River Parkway NorthUse the straight / right lanes.
32
Merge onto HR
14 mi·19 min·Hutchinson River Parkway
Use the straight / slight right lanes.
33
Keep slight left at fork
1.6 mi·2 min
Exit 16AToward I 684 North: BrewsterUse the slight left lane.
34
Merge onto I 684
3.0 mi·3 min·I 684
35
Take the exit onto 2
0.2 mi·28 sec·2
Exit 2Toward NY 120: Westchester County AirportUse the slight right lane.
36
Turn slight right onto Airport Road
120 ft·6 sec·Airport Road
37
Turn left onto NY 120
0.5 mi·53 sec·Lake Street
Use the left / straight / right lanes.
38
Continue on NY 120
1.5 mi·2 min·King Street
39
Turn right onto NY 22; NY 120
0.1 mi·15 sec·Mount Kisco Road
40
Continue on NY 22; NY 120
0.2 mi·23 sec·King Street
41
Turn left onto NY 120
4.1 mi·7 min·King Street
Use the left lane.
42
At end of road, turn right onto NY 117; NY 120
451 ft·16 sec·State Highway 117
43
Turn sharp left
162 ft·7 sec
44
Arrive at destination
Trip Plan
Given the 1 hour 40 minute duration, this is a perfect same-day trip, so leaving in the morning or early afternoon is ideal. With no planned stops, you have flexibility to add a break if needed. Watch for the transition from the Hutchinson River Parkway to King Street, as this is where the driving environment changes from parkway to surface road. Budget around $13 for fuel, and be aware that while it's a short drive, traffic can impact your travel time, especially during peak hours.
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 34.5 miles from Islip, NY, or about 49m into the drive.
The longest continuous stretch on this route runs about 24.7 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 15 miles or 22m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 34.5 miles or 49m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 24m
Traffic, exits, and arrival timing usually matter more near Chappaqua, 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.
Day 1
Settle into the route from Islip, NY
This is one driving day of about 69 miles and 1h 40m.
Your first comfortable stop window is around 15 miles from Islip, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on Southern State Parkway for about 24.7 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 27
5 decision points cluster between mile 3.6 and 43.9 — 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
40.9 mi into trip|~58m in|I 695 / Throgs Neck Expressway
Keep slight right at fork onto I 695 / Throgs Neck Expressway toward I 695 North: New Haven
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Exit 10
Toward I 695 North: New Haven
8
43.9 mi into trip|~1h 2m in
Take the exit toward Hutchinson Parkway North
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight right lane.
Exit 9
Toward Hutchinson Parkway North
Fuel & Cost
Regular Gas
$12.25 one way
$24.49 round trip
$4.51/gal25.4 MPG avg24 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.85
$13.16
$26.33
premium
$5.24
$14.23
$28.46
diesel
$5.35
$14.53
$29.07
Estimated Tolls: $6.55
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
$12
Tolls
$7
Meals
$25–$50
Total
$44–$69
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 24.1 kg one way.
Prices: EIA weekly data, 2026-06-01.
Driving Electric?
About $7 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
20.7
0
$7.25
$3.31
Efficient EV
17.3
0
$6.04
$2.76
EV Truck/SUV
27.6
0
$9.66
$4.42
Gas CO2
24 kg
EV CO2
8 kg (67% 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 May 24, 2026
Origin
Islip, NY
Afternoon
in Islip on Wednesday
Local time
4:05 PM
EDT
Current temp
58°F
Rain
E 12 to 18 mph99% chanceLive forecast
Rip Current Statement
Rip Current Statement issued May 24 at 2:38AM EDT until May 25 at 9:00PM EDT by NWS Upton NY
Destination
Chappaqua, NY
Afternoon
in Chappaqua on Wednesday
Local time
4:05 PM
EDT
Current temp
72°F
Unavailable
Live forecast
71°F
Corona, NY
35 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
14 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
1h 40m on the road
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
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...
7 mi from route
~17 min detour
Free
near mile 42.8
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...
8 mi from route
~19 min detour
Free
near mile 42.8
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
~31 min detour
Free
near mile 35.7
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...
12 mi from route
~29 min detour
Free
near mile 38.1
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...
13 mi from route
~33 min detour
Free
near mile 35.7
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This route is 74% highway, meaning you'll be on parkways for the majority of the 69 miles. The longest continuous stretch on a parkway is 24.7 miles on the Southern State Parkway. You'll transition from parkway driving to surface roads, specifically King Street, later in the trip. Expect a good amount of merging and exiting as you navigate through the suburban landscape.
74% highway — fuel and pacing are the main things to plan.
44 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 24.7 mi on Southern State Parkway.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on Southern State Parkway and Hutchinson River 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
Demanding - stay alert through the decision-heavy sections
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 69 miles you will encounter 27 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
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
Mostly flat terrain
504 ft12 ft
Total Climb
603 ft
Total Descent
125 ft
Highest Point
504 ft
~64.1 mi in
Elevation Range
492 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 Chappaqua, NY, road signs point toward Deer Park, So West: New York, Cross Island Parkway North, Hempstead Avenue West, Grandstand and Hutchinson Parkway North - 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
Chappaqua is a hamlet in the Town of New Castle in northern Westchester County, New York. Its most notable current residents are former President Bill Clinton and former Secretary of State Hillary Clinton.
Top landmarks
•Chappaqua — railway station in Chappaqua, the United States of America
Doable as a same-day drive at 1h 40m. Total distance: 69 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 40m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (74%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 24.7 miles on Southern State Parkway. The full list of main roads is in the Roads section above.
Expect about $6.55 in tolls one way, starting with Throgs Neck 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 1 rest area or service plaza 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 Chappaqua, NY before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Yes. At under 2 hours behind the wheel, this works well for families — plan one quick stop if you have younger kids.
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 Fire Island National Seashore (6 total within detour distance). See the National Parks section for detour distances and tips on detours.
Yes. A round trip is manageable in a single day if you plan a break at Chappaqua, NY before heading back.
