Smithtown, NY to Canandaigua, NY is 334.9 miles and takes about 7h 18m via I 81 and US 11, with a fuel budget near $56 and enough daylight to finish in a day. This drive stays within New York, taking you from the Northeast's coastal edge to its western Finger Lakes region. You'll spend most of your time on major roadways, making it a straightforward trip if you're looking to cover ground efficiently. Plan for a single day of driving, but consider an early start to make the most of daylight.
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
167.4 miles from Smithtown, NY
A natural place for your longest stop of the day
, about 3h 32m into the drive
.
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
Long Island Expressway
24.8 mi
33m
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
Traffic on I-80
Hour-of-day weekday pattern from 336 FHWA count stations on your route.
Peak
3 PM
~4,190 veh/hr typical
· worst 4,979
Quietest
1 AM
~446 veh/hr
Peak-to-quiet ratio
9.4×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 103 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 Smithtown, NY and Canandaigua, NY.
1
Start on NY 25; NY 25A
0.6 mi·51 sec·West Main Street
2
Keep slight left at fork onto NY 25; NY 25A
179 ft·5 sec·West Main Street
3
Continue on NY 25
4.0 mi·6 min·Jericho Turnpike
4
Take the ramp
0.2 mi·27 sec
Toward SM South: Bay Shore
5
Merge onto SM
1.9 mi·2 min·Sunken Meadow State Parkway
6
Continue on SA
0.8 mi·49 sec·Sagtikos State Parkway
7
Take the exit
0.1 mi·16 sec
Exit S1WToward I 495 West: New YorkUse the slight right lane.
8
Keep slight left at fork
0.2 mi·23 sec
Toward I 495 West: New YorkUse the straight / slight right lanes.
9
Turn straight onto LIE North Service Road
0.4 mi·33 sec·LIE North Service Road
10
Turn straight onto North Service Road
0.1 mi·14 sec·North Service Road
11
Take the ramp
0.2 mi·21 sec
Toward I 495 West: New York
12
Merge onto I 495
25 mi·33 min·Long Island Expressway
Use the straight / slight right lanes.
13
Take the exit
0.2 mi·27 sec
Exit 31N-SToward Cross Island Parkway, Whitestone Bridge, Kennedy AirportUse the straight / slight right lanes.
14
Keep slight right at fork
0.3 mi·38 sec
Exit 31NToward Cross Island Parkway North, Whitestone BridgeUse the slight left / slight right lanes.
15
Merge onto CI
3.1 mi·4 min·Cross Island Parkway
Use the straight / slight right lanes.
16
Take the exit
0.6 mi·1 min
Exit 33Toward I 295 North: Throgs Neck Bridge, Bronx, New EnglandUse the straight / slight right lanes.
17
Merge onto I 295
1.8 mi·3 min·Throgs Neck Bridge
18
Continue on I 295
0.7 mi·1 min·Throgs Neck Expressway
Use the straight / slight right lanes.
19
Keep slight left at fork onto I 295
6.6 mi·8 min·Cross Bronx Expressway
Use the straight / slight right lanes.
20
Keep slight left at fork onto I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
Toward Upper Level
21
Continue on I 95; US 1
0.6 mi·59 sec·George Washington Bridge (upper level)
22
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
23
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.
24
Keep slight left at fork onto I 95 EXPR; NJTP
0.1 mi·8 sec·I 95 EXPR; NJTP
25
Take the exit
0.2 mi·22 sec
Toward I 95 South, NJTP South: HackensackUse the straight / slight right lanes.
26
Keep slight left at fork
0.4 mi·29 sec
Toward I 95 South, NJTP South: HackensackUse the slight left / slight right lanes.
27
Merge onto I 95; NJTP
2.0 mi·2 min·New Jersey Turnpike
Use the straight / slight right lanes.
28
Take the exit
0.8 mi·1 min
Exit 69Toward I 80 West: Paterson, HackensackUse the straight / slight right lanes.
29
Continue on I 80
68 mi·1 hr 20 min·Christopher Columbus Highway
Use the straight / slight right lanes.
30
Keep slight left at fork onto I 80
5.5 mi·8 min·Keystone Shortway
Use the straight / slight right lanes.
31
Keep slight left at fork onto I 80
12 mi·15 min·Keystone Shortway
32
Take the exit
0.7 mi·46 sec
Exit 293Toward I 380 North: Scranton
33
Continue on I 380
28 mi·30 min·I 380
Use the straight lane.
34
Merge onto I 81
58 mi·1 hr 9 min·I 81
Use the straight lane.
35
Keep slight right at fork onto I 81
1.8 mi·2 min·I 81
Toward I 81 North: Syracuse, Albany
36
Keep slight left at fork onto I 81
14 mi·16 min·I 81
Toward I 81 North: Syracuse
37
Take the exit
0.3 mi·32 sec
Exit 8Toward NY 26 North: Whitney Point, Lisle
38
Turn right onto NY 26
0.5 mi·43 sec·NY 26
39
At end of road, turn left onto US 11; NY 26
0.1 mi·9 sec·US 11; NY 26
40
Continue on US 11; NY 79
31 mi·39 min·US 11; NY 79
41
Keep slight right at fork onto NY 79
0.1 mi·19 sec·Seneca Way
42
Continue on NY 79
0.9 mi·2 min·East Seneca Street
Use the straight lane.
43
Turn right onto Taughannock Boulevard
338 ft·15 sec·Taughannock Boulevard
44
Turn left onto NY 96
0.2 mi·21 sec·West Buffalo Street
45
Continue on NY 96
1.0 mi·2 min·Cliff Street
46
Continue on NY 96
8.7 mi·12 min·Trumansburg Road
47
Continue on NY 96
1.4 mi·2 min·East Main Street
48
Continue on NY 96
0.1 mi·11 sec·Trumansburg Road
49
Continue on NY 96
4.0 mi·5 min·State Highway 96
50
Turn right onto CR 141A
1.5 mi·2 min·Powell Road
51
Continue on CR 141
0.9 mi·1 min·County Road 141
52
Turn left onto NY 89
3.4 mi·4 min·State Highway 89
53
Turn left onto Center Road
1.4 mi·1 min·Center Road
54
Turn right onto NY 96
3.0 mi·4 min·State Highway 96
55
Continue on NY 96
485 ft·15 sec·North Town Line Road
56
Continue on NY 96A
0.2 mi·24 sec·North Street
57
Continue on NY 96A
17 mi·23 min·State Highway 96A
58
Turn left onto US 20; NY 5
1.6 mi·2 min·Waterloo-Geneva Road
59
Continue on US 20; NY 5
1.1 mi·1 min·Lake Front Drive
60
Continue on US 20; NY 5
1.4 mi·3 min·Hamilton Street
61
Continue on US 20; NY 5
0.6 mi·1 min·Canandaigua Road
62
Continue on US 20; NY 5
11 mi·17 min·Routes 5 and 20
63
Continue on US 20; NY 5
2.0 mi·3 min·Eastern Boulevard
64
Keep slight left at fork onto US 20; NY 5
1.0 mi·1 min·Western Boulevard
65
Turn right onto Middle Cheshire Road
0.2 mi·20 sec·Middle Cheshire Road
Use the straight / right lanes.
66
Turn right onto Parrish Street
0.2 mi·38 sec·Parrish Street
67
Turn right
350 ft·27 sec
68
At end of road, turn right
166 ft·12 sec
69
Turn right
41 ft·2 sec
70
Arrive at destination
Trip Plan
Given the 7h 18m duration and 334.9 miles, leaving Smithtown early in the morning is your best bet for a single-day trip. This allows you ample time for your two planned stops without feeling rushed. The primary roads are I 81 and US 11, so keep an eye on exit numbers as you approach your destination. The estimated fuel cost is $56, so be sure to budget accordingly and refuel before you get too low, especially before longer stretches on I 81. The 73.8-mile segment on I 81 is a good opportunity to maintain cruising speed.
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 167.4 miles from Smithtown, 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 40m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 167.4 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 47m
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 Smithtown, 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 Smithtown, NY
This is one driving day of about 334.9 miles and 7h 18m.
Your first comfortable stop window is around 74 miles from Smithtown, 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.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 43
5 decision points cluster between mile 7.6 and 49.1 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
8
7.6 mi into trip|~10m in
Keep slight left at fork toward I 495 West: New York
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Toward I 495 West: New York
8
33.3 mi into trip|~46m in
Take the exit toward Cross Island Parkway, Whitestone Bridge, Kennedy Airport
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.
Exit 31N-S
Toward Cross Island Parkway, Whitestone Bridge,...
10
33.5 mi into trip|~46m in
Keep slight right at fork toward Cross Island Parkway North, Whitestone Bridge
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left / slight right lanes.
Exit 31N
Toward Cross Island Parkway North, Whitestone B...
8
36.9 mi into trip|~51m in
Take the exit toward I 295 North: Throgs Neck Bridge, Bronx, New England
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.
Exit 33
Toward I 295 North: Throgs Neck Bridge, Bronx,...
8
49.1 mi into trip|~1h 9m 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
Fuel & Cost
Regular Gas
$59.16 one way
$118.32 round trip
$4.49/gal25.4 MPG avg117 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.86
$64.01
$128.03
premium
$5.28
$69.56
$139.13
diesel
$6.18
$81.47
$162.94
Estimated Tolls: $23.11
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
Jericho Turnpike
(4 mi)$0.28
New Jersey Turnpike
(2 mi)$0.28
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
$59
Tolls
$23
Meals
$25–$50
Total
$107–$132
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 117.2 kg one way.
Prices: EIA weekly data, 2026-10-12.
Driving Electric?
About $35 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
100.5
1
$35.16
$16.08
Efficient EV
83.7
0
$29.30
$13.40
EV Truck/SUV
134
1
$46.89
$21.43
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 Oct 17, 2026
Origin
Smithtown, NY
Afternoon
in Smithtown on Saturday
Local time
3:11 PM
EDT
Current temp
52°F
Rain Showers Likely then Mostly Cloudy
N 15 mph61% chanceLive forecast
Freeze Warning
Freeze Warning issued October 17 at 2:20AM EDT until October 18 at 9:00AM EDT by NWS Upton NY
Freeze Warning
Freeze Warning issued October 17 at 1:29AM EDT until October 18 at 9:00AM EDT by NWS Buffalo NY
Destination
Canandaigua, NY
Afternoon
in Canandaigua on Saturday
Local time
3:11 PM
EDT
Current temp
46°F
Chance Rain Showers then Partly Sunny
NW 8 to 15 mph45% chanceLive forecast
Freeze Warning
Freeze Warning issued October 17 at 2:20AM EDT until October 18 at 9:00AM EDT by NWS Upton NY
Freeze Warning
Freeze Warning issued October 17 at 1:29AM EDT until October 18 at 9:00AM EDT by NWS Buffalo NY
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
6 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 18m 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.
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 311.8
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
~22 min detour
Free
near mile 46.2
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 46.2
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 46.2
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This trip is mostly highway, with 61% of the drive on major roads. You'll encounter the longest stretch without a major turn at 73.8 miles on I 81. Expect a steady pace for much of the way, transitioning to US 11 for the final portion of the drive. With two designated stops, you can break up the 7-hour drive effectively.
61% highway — fuel and pacing are the main things to plan.
70 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 73.8 mi on I 81.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on I 81 and Christopher Columbus Highway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 7.6 miles in.
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 43 significant decision points across 334.9 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 7.6 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 33.3 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 33.5 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Elevation Profile
Gently rolling terrain
1,944 ft-3 ft
Total Climb
3,000 ft
Total Descent
2,259 ft
Highest Point
1,944 ft
~143.5 mi in
Elevation Range
1,946 ft
Notable High Points
1,944 ft at ~143.5 miles+1,037 ft prominence
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Smithtown, NY and Canandaigua, NY, road signs point toward Kennedy Airport, Cross Island Parkway North, Bronx, New England, Upper Level and Njtp South: Hackensack - among others.
Smithtown is a town of 117,000 people (2016) in Suffolk County, on Long Island, in New York. Smithtown is comprised of the villages and hamlets of Commack (in part, with the Town of Huntington), Fort Salonga (in part, with the Town of Huntington), Hauppauge (in part, with the Town of Islip), Head of the Harbor, Kings Park, Lake Ronkonkoma (in part with the Town of Brookhaven and Town of Islip), Nesconset, Nissequogue, Smithtown, St. James, & Village of the Branch.
One of the oldest cities in the Finger Lakes region of New York, Canandaigua has a long history as a major crossroads. Its name derives from a Seneca word meaning "The Chosen Spot", and its position at the northern end of Canandaigua Lake certainly justifies the moniker. With a well-preserved historic downtown, a magnificent 19th-century mansion with gardens, a modern and very trendy wine and culinary center, and (of course) the always-excellent boating on the lake, Canandaigua today has just as much to offer a visitor as it did in its heyday... if not more.
Doable as a same-day drive at 7h 18m. Total distance: 334.9 miles.
Family Friendly
Moderate complexity with 2 natural rest stops along the way.
Solo Traveler
7h 18m drive, plan rest stops for pacing.
Frequently Asked Questions
The longest stretch is about 73.8 miles on I 81. The full list of main roads is in the Roads section above.
Expect about $23.11 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.
Yes — we found about 28 rest areas or service plazas 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 Canandaigua, 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 2 meaningful breaks. There are 28 rest areas along the route for bathroom stops.
The main spots that need attention: at 7.6 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 33.3 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 33.5 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — Hamilton Grange National Memorial, General Grant National Memorial and Women's Rights National Historical Park (6 total within detour distance). See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 7.3 hours each way, a round trip means 14.6 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Canandaigua, NY before the return drive.
