The drive from Islip, NY to Canandaigua, NY covers 335.9 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 I 81, Christopher Columbus Highway, US 11 for much of the mileage,
and the overall profile is turn-heavy local drive.
The longest uninterrupted segment is about 73.8 miles on I 81.
At current regular gas prices, budget about $55.29 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
167.9 miles from Islip, NY
A natural place for your longest stop of the day
, about 3h 32m into the drive
.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 7h 19m. Total distance: 335.9 miles.
Family Friendly
Moderate complexity with 2 natural rest stops along the way.
Solo Traveler
7h 19m drive, plan rest stops for pacing.
Drive Character
Expect a 7h 19m drive with frequent turns across 335.9 miles of local and secondary roads.
Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 78 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
I 81 is the longest continuous segment at about 73.8 miles.
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 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 46 significant decision points across 335.9 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.
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
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
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 Canandaigua, NY, road signs point toward Cross Island Parkway North, Hempstead Avenue West, Grandstand, Upper Level, Njtp South: Hackensack and Hackensack - among others.
Cross Island Parkway North
29.4 mi in|~40m
Hempstead Avenue West
31.1 mi in|~43m
Grandstand
31.3 mi in|~43m
Upper Level
47.5 mi in|~1h 6m|via I 95; US 1
Njtp South: Hackensack
50 mi in|~1h 10m
Hackensack
52.6 mi in|~1h 14m
Albany
225.4 mi in|~4h 41m|via I 81
Lisle
241.2 mi in|~5h
Main Roads
Road
Distance
Duration
I 81
73.8 mi
1h 28m
Christopher Columbus Highway
68.2 mi
1h 20m
US 11
30.6 mi
40m
I 380
27.7 mi
30m
Southern State Parkway
24.7 mi
31m
Keystone Shortway
17.3 mi
24m
State Highway 96A
17.1 mi
23m
Routes 5 and 20
11.2 mi
17m
Longest stretch:
I 81
— 73.8 mi, about 1h 28m
Turn-by-Turn Driving Directions
Step-by-step road directions between Islip, NY and Canandaigua, 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
12 mi·15 min·Keystone Shortway
40
Take the exit
0.7 mi·46 sec
Exit 293Toward I 380 North: Scranton
41
Continue on I 380
28 mi·30 min·I 380
Use the straight lane.
42
Merge onto I 81
58 mi·1 hr 9 min·I 81
Use the straight lane.
43
Keep slight right at fork onto I 81
1.8 mi·2 min·I 81
Toward I 81 North: Syracuse, Albany
44
Keep slight left at fork onto I 81
14 mi·16 min·I 81
Toward I 81 North: Syracuse
45
Take the exit
0.3 mi·32 sec
Exit 8Toward NY 26 North: Whitney Point, Lisle
46
Turn right onto NY 26
0.5 mi·43 sec·NY 26
47
At end of road, turn left onto US 11; NY 26
0.1 mi·9 sec·US 11; NY 26
48
Continue on US 11; NY 79
31 mi·39 min·US 11; NY 79
49
Keep slight right at fork onto NY 79
0.1 mi·19 sec·Seneca Way
50
Continue on NY 79
0.9 mi·2 min·East Seneca Street
Use the straight lane.
51
Turn right onto Taughannock Boulevard
338 ft·15 sec·Taughannock Boulevard
52
Turn left onto NY 96
0.2 mi·21 sec·West Buffalo Street
53
Continue on NY 96
1.0 mi·2 min·Cliff Street
54
Continue on NY 96
8.7 mi·12 min·Trumansburg Road
55
Continue on NY 96
1.4 mi·2 min·East Main Street
56
Continue on NY 96
0.1 mi·11 sec·Trumansburg Road
57
Continue on NY 96
4.0 mi·5 min·State Highway 96
58
Turn right onto CR 141A
1.5 mi·2 min·Powell Road
59
Continue on CR 141
0.9 mi·1 min·County Road 141
60
Turn left onto NY 89
3.4 mi·4 min·State Highway 89
61
Turn left onto Center Road
1.4 mi·1 min·Center Road
62
Turn right onto NY 96
3.0 mi·4 min·State Highway 96
63
Continue on NY 96
485 ft·15 sec·North Town Line Road
64
Continue on NY 96A
0.2 mi·24 sec·North Street
65
Continue on NY 96A
17 mi·23 min·State Highway 96A
66
Turn left onto US 20; NY 5
1.6 mi·2 min·Waterloo-Geneva Road
67
Continue on US 20; NY 5
1.1 mi·1 min·Lake Front Drive
68
Continue on US 20; NY 5
1.4 mi·3 min·Hamilton Street
69
Continue on US 20; NY 5
0.6 mi·1 min·Canandaigua Road
70
Continue on US 20; NY 5
11 mi·17 min·Routes 5 and 20
71
Continue on US 20; NY 5
2.0 mi·3 min·Eastern Boulevard
72
Keep slight left at fork onto US 20; NY 5
1.0 mi·1 min·Western Boulevard
73
Turn right onto Middle Cheshire Road
0.2 mi·20 sec·Middle Cheshire Road
Use the straight / right lanes.
74
Turn right onto Parrish Street
0.2 mi·38 sec·Parrish Street
75
Turn right
350 ft·27 sec
76
At end of road, turn right
166 ft·12 sec
77
Turn right
41 ft·2 sec
78
Arrive at destination
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 167.9 miles from Islip, NY, or about 3h 32m into the drive.
The longest continuous stretch on this route runs about 73.8 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 39m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 167.9 miles or 3h 32m 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 48m
Traffic, exits, and arrival timing usually matter more near Canandaigua, 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.
Day 1
Settle into the route from Islip, NY
This is one driving day of about 335.9 miles and 7h 19m.
Your first comfortable stop window is around 74 miles from Islip, 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 I 81 for about 73.8 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 167.9 mi from Islip, NY
· 3h 32m into the drive
Place data sourced from public business listings. Hours and availability may vary.
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...
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...
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 312.7
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...
9 mi from route
~23 min detour
Free
near mile 46.3
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 46.3
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 46.3
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
100.8
1
$35.27
$16.12
Efficient EV
84
0
$29.39
$13.44
EV Truck/SUV
134.4
1
$47.03
$21.50
Gas CO2
118 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 15, 2026
Origin
Islip, NY
Late night
in Islip on Friday
Local time
2:10 AM
EDT
Current temp
44°F
Unavailable
Live forecast
Destination
Canandaigua, NY
Late night
in Canandaigua on Friday
Local time
2:10 AM
EDT
Current temp
37°F
Unavailable
Live 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
7 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
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 Islip, NY to Canandaigua, NY covers 335.9 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 I 81, Christopher Columbus Highway, US 11. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 167.9 miles from Islip, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $55.29 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 335.9 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.
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.
Between Islip, NY and Canandaigua, NY, road signs point toward Cross Island Parkway North, Hempstead Avenue West, Grandstand, Upper Level, Njtp South: Hackensack and Hackensack - among others.
Yes. Nearby national parks include Hamilton Grange National Memorial, General Grant National Memorial and Women's Rights National Historical Park. There are 6 parks within detour distance of this route.
