The drive from Canandaigua, NY to Islip, NY covers 335.4 miles and takes about 7h 19m behind the wheel.
This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Keystone Shortway, I 81, Southern State Parkway for much of the mileage,
and the overall profile is turn-heavy local drive.
The longest uninterrupted segment is about 80 miles on Keystone Shortway.
At current regular gas prices, budget about $55.21 one way before food or hotel costs.
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
167.7 miles from Canandaigua, NY
A natural place for your longest stop of the day
, about 3h 47m into the drive
.
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 19m. Total distance: 335.4 miles.
Family Friendly
Moderate complexity with 2 natural rest stops along the way.
Solo Traveler
7h 19m drive, plan rest stops for pacing.
Scenic Drive
Turn-heavy local drive route profile with national parks nearby.
Drive Character
Expect a 7h 19m drive with frequent turns across 335.4 miles of local and secondary roads.
This route has more turning and local-road decision points than a simple highway run.
There are about 83 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Keystone Shortway is the longest continuous segment at about 80 miles.
Elevation Profile
Gently rolling terrain
1,937 ft12 ft
Total Climb
2,075 ft
Total Descent
2,858 ft
Highest Point
1,937 ft
~191.7 mi in
Elevation Range
1,925 ft
Notable High Points
1,937 ft at ~191.7 miles+1,023 ft prominence
How Hard Is This Drive?
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 168.4 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 46 significant decision points across 335.4 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 168.4 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 282.9 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 283.2 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Critical Maneuvers
5 of 46 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
9
168.4 mi into trip|~3h 48m 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
282.9 mi into trip|~6h 4m 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
283.2 mi into trip|~6h 4m 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
292.6 mi into trip|~6h 19m 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
330.8 mi into trip|~7h 10m 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
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Canandaigua, NY and Islip, NY, road signs point toward Mt Pocono, Milford, New York City, Leonia, Teaneck and George Washington Bridge Upper Level - among others.
Mt Pocono
168.4 mi in|~3h 48m|via US 6
Milford
169.1 mi in|~3h 49m|via I 84; I 380
New York City
282.9 mi in|~6h 4m
Leonia
283.2 mi in|~6h 4m
Teaneck
283.2 mi in|~6h 4m
George Washington Bridge Upper Level
285.5 mi in|~6h 9m
Cross Island Parkway South
304.1 mi in|~6h 35m
Southern State Parkway East
305.6 mi in|~6h 37m
Eastern Long Island
305.6 mi in|~6h 37m
Main Roads
Road
Distance
Duration
Keystone Shortway
80 mi
1h 37m
I 81
73.5 mi
1h 28m
Southern State Parkway
24.7 mi
31m
I 380
23.6 mi
25m
State Highway 96A
17.1 mi
23m
State Highway 79
15.2 mi
17m
Routes 5 and 20
11.2 mi
17m
Slaterville Road
11.1 mi
16m
Longest stretch:
Keystone Shortway
— 80 mi, about 1h 37m
Turn-by-Turn Driving Directions
Step-by-step road directions between Canandaigua, NY and Islip, NY.
1
Start on this road
41 ft·3 sec·this road
2
Turn right
114 ft·8 sec
3
Turn right
350 ft·31 sec
4
Turn left onto Parrish Street
0.2 mi·41 sec·Parrish Street
5
Turn left onto Middle Cheshire Road
0.2 mi·27 sec·Middle Cheshire Road
6
Turn left onto US 20; NY 5; NY 21
1.0 mi·1 min·Western Boulevard
7
Continue on US 20; NY 5
2.0 mi·3 min·Eastern Boulevard
Use the left / straight / right lanes.
8
Continue on US 20; NY 5
11 mi·17 min·Routes 5 and 20
9
Continue on US 20; NY 5
0.6 mi·1 min·Canandaigua Road
10
Continue on US 20; NY 5
1.4 mi·3 min·Hamilton Street
11
Continue on US 20; NY 5
1.1 mi·1 min·Lake Front Drive
12
Continue on US 20; NY 5
1.6 mi·2 min·Waterloo-Geneva Road
13
Turn right onto NY 96A
10 mi·14 min·State Highway 96A
14
Keep slight left at fork onto NY 96A
6.7 mi·9 min·State Highway 96A
15
Continue on NY 96A
0.2 mi·26 sec·North Street
16
Continue on NY 96
485 ft·13 sec·North Town Line Road
17
Continue on NY 96
3.0 mi·4 min·State Highway 96
18
Turn left onto Center Road
1.4 mi·1 min·Center Road
19
Turn right onto NY 89
3.4 mi·4 min·State Highway 89
20
Turn right onto CR 141
0.9 mi·1 min·County Road 141
21
Continue on CR 141A
1.5 mi·2 min·Powell Road
22
Turn left onto NY 96
4.0 mi·5 min·State Highway 96
23
Continue on NY 96
0.1 mi·11 sec·Trumansburg Road
24
Continue on NY 96
1.4 mi·2 min·West Main Street
25
Continue on NY 96
8.7 mi·12 min·Trumansburg Road
26
Continue on NY 96
1.0 mi·2 min·Cliff Street
27
Continue on NY 96
0.2 mi·22 sec·West Buffalo Street
28
Turn right onto Taughannock Boulevard
523 ft·24 sec·Taughannock Boulevard
29
Turn left onto NY 79
510 ft·11 sec·West State Street
30
Turn right onto NY 13; NY 34; NY 96; NY 79
345 ft·12 sec·South Fulton Street
Use the right lane.
31
Turn left onto NY 79
0.8 mi·2 min·West Green Street
Use the slight left lane.
32
Continue on NY 79
1.1 mi·2 min·East State Street
33
Continue on NY 79
11 mi·16 min·Slaterville Road
34
Continue on NY 79
15 mi·17 min·State Highway 79
35
Continue on NY 79
3.1 mi·3 min·Main Street
36
Turn right onto NY 26
0.6 mi·47 sec·NY 26
37
Take the exit
0.3 mi·40 sec
Toward I 81 South
38
Merge onto I 81
20 mi·24 min·I 81
39
Keep slight right at fork onto I 81
53 mi·1 hr 3 min·I 81
Toward I 81 South: ScrantonUse the straight lane.
40
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.
41
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.
42
Keep slight right at fork onto I 380
24 mi·25 min·I 380
Exit 4Toward I 380 South: Mount Pocono
43
Keep slight left at fork
1.0 mi·1 min
Exit 1BToward I 80 East: Stroudsburg
44
Merge onto I 80
80 mi·1 hr 37 min·Keystone Shortway
Use the straight / right lanes.
45
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.
46
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.
47
Keep slight right at fork
0.4 mi·38 sec
Exit 70A-BToward Leonia, TeaneckUse the slight right lane.
48
Turn right
0.2 mi·35 sec
Exit 70AToward LeoniaUse the straight / slight right lanes.
49
Turn straight onto CR 56
454 ft·9 sec·Degraw Avenue
50
Continue on CR 56
1.1 mi·2 min·Fort Lee Road
Use the straight / right lanes.
51
Continue on CR 56
469 ft·13 sec·Main Street
52
Take the ramp
472 ft·12 sec
Toward George Washington Bridge
53
Merge onto US 1; US 9; US 46
0.3 mi·28 sec·Bergen Boulevard
Use the straight / slight right lanes.
54
Take the exit
312 ft·4 sec
Toward George Washington Bridge Upper Level
55
Merge onto I 95 EXPR
0.3 mi·20 sec·I 95 EXPR
Use the straight / slight right lanes.
56
Keep slight left at fork onto I 95 EXPR
0.8 mi·1 min·I 95 EXPR
57
Continue on I 95; US 1; US 9
0.6 mi·1 min·George Washington Bridge (upper level)
Use the straight / slight right lanes.
58
Continue on I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
59
Continue on I 95; US 1
4.7 mi·6 min·Cross Bronx Expressway
Use the straight / slight right lanes.
60
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.
61
Merge onto I 295
0.6 mi·58 sec·Throgs Neck Expressway
62
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
Use the straight / slight right lanes.
63
Continue on I 295
5.0 mi·5 min·Clearview Expressway
Use the straight / slight right lanes.
64
Continue on NY 24
0.7 mi·1 min·Hollis Court Boulevard
Use the straight lane.
65
At end of road, turn left onto NY 24
0.2 mi·35 sec·Jamaica Avenue
Use the left lane.
66
Turn right onto Hempstead Avenue
0.9 mi·2 min·Hempstead Avenue
67
Turn right onto 225th Street
228 ft·9 sec·225th Street
Use the right lane.
68
Take the ramp
0.2 mi·28 sec
Toward Cross Island Parkway South, Verrazano Bridge
69
Merge onto CI
1.3 mi·1 min·Cross Island Parkway
Use the straight / slight right lanes.
70
Take the exit
0.5 mi·1 min
Exit 25AToward Southern State Parkway East, Eastern Long IslandUse the slight left / straight lanes.
71
Merge onto SO
25 mi·31 min·Southern State Parkway
Use the straight / slight right lanes.
72
Keep slight left at fork onto SO
0.2 mi·16 sec·Southern State Parkway
Use the straight / slight right lanes.
73
Take the exit
0.2 mi·31 sec
Exit 41SToward Bay Shore Road South, Bay ShoreUse the slight right lane.
74
Turn straight onto CR 57
0.5 mi·1 min·Bay Shore Road
75
Continue on CR 57
0.3 mi·43 sec·Howells Road
76
Turn straight onto CR 57
341 ft·6 sec·Sunrise Highway
77
Keep slight right at fork onto CR 57
0.6 mi·1 min·Howells Road
Toward Howells Road SouthUse the right lane.
78
Continue on CR 57
0.2 mi·24 sec·Roosevelt Street
79
Continue on CR 57
0.7 mi·1 min·3rd Avenue
80
At end of road, turn left onto NY 27A
1.1 mi·1 min·East Main Street
81
Continue on Montauk Highway
0.2 mi·17 sec·Montauk Highway
82
Continue on NY 27A
0.8 mi·1 min·Main Street
83
Arrive at destination
NY 27A
Trip Plan
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 167.7 miles from Canandaigua, NY, or about 3h 47m into the drive.
The longest continuous stretch on this route runs about 80 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 74 miles or 1h 55m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 167.7 miles or 3h 47m 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 55m
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 Canandaigua, 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 Canandaigua, NY
This is one driving day of about 335.4 miles and 7h 19m.
Your first comfortable stop window is around 74 miles from Canandaigua, 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 Keystone Shortway for about 80 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 167.7 mi from Canandaigua, NY
· 3h 47m into the drive
The midpoint is around 167.7 miles from Canandaigua, NY, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel check
Top up before Keystone Shortway if your tank is already low. That segment runs about 80 miles.
Arriving in Islip, NY
The final approach into Islip, NY usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Islip, NY.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
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...
3 mi from route
~7 min detour
Free
near mile 289.1
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...
4 mi from route
~9 min detour
Free
near mile 289.1
Women’s Rights National Historical Park tells the story of the first Women’s Rights Convention, held in Seneca Falls, New York on July 19-20, 1848. It is a story of struggles for civil rights, human r...
7 mi from route
~17 min detour
Free
near mile 23.1
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 289.1
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
~26 min detour
Free
near mile 289.1
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...
11 mi from route
~28 min detour
Free
near mile 289.1
Station data from NREL Alternative Fuel Stations database.
Driving Electric?
About $35 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
100.6
1
$35.22
$16.10
Efficient EV
83.9
0
$29.35
$13.42
EV Truck/SUV
134.2
1
$46.96
$21.47
Gas CO2
117 kg
EV CO2
39 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 Apr 18, 2026
Origin
Canandaigua, NY
Morning
in Canandaigua on Saturday
Local time
10:15 AM
EDT
Current temp
37°F
Unavailable
Live forecast
Destination
Islip, NY
Morning
in Islip on Saturday
Local time
10:15 AM
EDT
Current temp
50°F
Partly Cloudy
NE 3 mph0% chanceLive forecast
57°F
Ramapo, NY
168 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
13 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 19m 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.
Frequently Asked Questions
The drive from Canandaigua, NY to Islip, NY covers 335.4 miles and takes about 7h 19m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Keystone Shortway, I 81, Southern State Parkway. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 167.7 miles from Canandaigua, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $55.21 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Start early — leave by 6-7 AM to arrive at a reasonable hour. This is a long drive — plan for a morning departure or consider splitting it into two days.
Plan about 2 meaningful breaks for fuel, food, or rest. Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
This is a demanding drive. With 46 significant decision points across 335.4 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.
The main spots that need attention: at 168.4 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 282.9 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 283.2 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Between Canandaigua, NY and Islip, NY, road signs point toward Mt Pocono, Milford, New York City, Leonia, Teaneck and George Washington Bridge Upper Level - among others.
Gently rolling terrain. The route ranges from 12 ft to 1,937 ft elevation with about 2,075 ft of total climbing. There is 1 notable high point along the way.
How this page is built
Compiled by the Trip.ovh planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, EIA for fuel prices, USGS 3DEP for elevation, NREL for EV charging, and NPS for national parks. See our methodology for refresh cadence and limitations.
