Canandaigua, NY to Sheepshead Bay, NY is 295.8 miles and takes about 6h 40m via I 81 and I 380, with a fuel budget near $50 and enough daylight to finish in a day. This drive stays within the Northeast region, primarily traversing New York and passing through parts of Pennsylvania. With a highway share of 56%, you'll spend a significant portion of your time on major interstates, but the profile indicates a good amount of travel on surface roads as well. This route is a solid option for a single-day trip if you're looking for a straightforward drive between these two points.
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
147.9 miles from Canandaigua, NY
A natural place for your longest stop of the day
, about 3h 24m into the drive
.
Main Roads
Road
Distance
Duration
I 81
73.5 mi
1h 28m
Keystone Shortway
63.3 mi
1h 19m
I 380
23.6 mi
25m
State Highway 96A
17.1 mi
23m
Essex Freeway
15.8 mi
20m
State Highway 79
15.2 mi
17m
Routes 5 and 20
11.2 mi
17m
Slaterville Road
11.1 mi
16m
Longest stretch:
I 81
— 73.5 mi, about 1h 28m
Traffic on I-80
Hour-of-day weekday pattern from 196 FHWA count stations on your route.
Peak
3 PM
~4,254 veh/hr typical
· worst 5,020
Quietest
1 AM
~471 veh/hr
Peak-to-quiet ratio
9×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 52 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 Canandaigua, NY and Sheepshead Bay, 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
63 mi·1 hr 19 min·Keystone Shortway
Use the straight / right lanes.
45
Take the exit
0.7 mi·49 sec
Exit 47AToward I 280 East: The Oranges, Newark
46
Continue on I 280
16 mi·20 min·Essex Freeway
Use the straight / right lanes.
47
Take the exit
0.6 mi·1 min
Exit 17AToward CR 508 East: Jersey City
48
Merge onto CR 508
2.0 mi·3 min·Newark-Jersey City Turnpike
Use the straight / slight right lanes.
49
Continue on NJ 7
0.5 mi·43 sec·New Wittpenn Bridge
Use the straight / slight right lanes.
50
Take the exit
0.2 mi·28 sec
Toward NJ 139 East: Hoboken, Holland TunnelUse the slight right lane.
51
Keep slight left at fork
0.4 mi·47 sec
Toward Holland Tunnel, Lincoln TunnelUse the straight / slight left lanes.
52
Turn straight
0.3 mi·35 sec
Use the straight lane.
53
Merge onto NJ 139
0.7 mi·1 min·Conrail Viaduct
54
Continue on NJ 139
0.4 mi·32 sec·12th Street Viaduct
55
Continue on I 78
0.3 mi·54 sec·12th Street
Use the straight / right lanes.
56
Keep slight left at fork onto I 78
1.9 mi·4 min·Holland Tunnel
Toward Holland Tunnel, Manhattan
57
Take the exit
428 ft·14 sec
Toward NY 9A
58
Turn slight left onto Laight Street
0.2 mi·48 sec·Laight Street
Toward NY 9A
59
At end of road, turn left onto NY 9A
0.9 mi·2 min·West Street
Use the straight lane.
60
Take the exit
2.6 mi·5 min
Exit 2Toward Hugh L Carey Tunnel, BrooklynUse the left lane.
61
Continue on I 278
0.6 mi·50 sec·Gowanus Expressway
62
Take the exit onto NY 27
1.5 mi·2 min·NY 27
Exit 24Toward NY 27 East: Prospect ExpresswayUse the slight left / straight lanes.
63
Take the exit onto NY 27
0.4 mi·47 sec·NY 27
Exit 5Toward NY 27 East: SUNY Downstate Medical CenterUse the slight right lane.
64
Turn left onto NY 27
0.3 mi·45 sec·Caton Avenue
65
Turn right onto NY 27
2.7 mi·5 min·Coney Island Avenue
Use the straight / right lanes.
66
Turn left onto Avenue P
0.5 mi·1 min·Avenue P
Use the left lane.
67
Turn right onto Ocean Avenue
1.4 mi·2 min·Ocean Avenue
68
Turn left onto Avenue Y
0.3 mi·1 min·Avenue Y
Use the left lane.
69
Arrive at destination
Avenue Y
Trip Plan
Given the 6h 40m estimated drive time, leaving Canandaigua in the morning should allow you to reach Sheepshead Bay before evening. The $50 fuel cost is an estimate, so check current prices before you depart. With only one recommended stop and a longest stretch of 73.5 miles on I 81, you can plan your breaks accordingly. Consider stopping for fuel or a meal around the halfway point to break up the drive. Keep an eye on traffic, especially as you get closer to the New York City metropolitan area, which can impact your travel time.
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 147.9 miles from Canandaigua, NY, or about 3h 24m into the drive.
The longest continuous stretch on this route runs about 73.5 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 65 miles or 1h 41m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 147.9 miles or 3h 24m 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 17m
Traffic, exits, and arrival timing usually matter more near Sheepshead Bay, 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.
Day 1
Settle into the route from Canandaigua, NY
This is one driving day of about 295.8 miles and 6h 40m.
Your first comfortable stop window is around 65 miles from Canandaigua, 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 I 81 for about 73.5 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 43
5 decision points cluster between mile 115 and 285.7 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
7
115 mi into trip|~2h 45m in|I 81
Keep slight right at fork onto I 81 toward I 81 South: Scranton
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight lane.
Toward I 81 South: Scranton
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...
7
280.5 mi into trip|~6h 7m in
Take the exit toward NJ 139 East: Hoboken, Holland Tunnel
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Toward NJ 139 East: Hoboken, Holland Tunnel
8
280.7 mi into trip|~6h 8m in
Keep slight left at fork toward Holland Tunnel, Lincoln Tunnel
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight left lanes.
Toward Holland Tunnel, Lincoln Tunnel
8
285.7 mi into trip|~6h 20m in
Take the exit toward Hugh L Carey Tunnel, Brooklyn
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the left lane.
Exit 2
Toward Hugh L Carey Tunnel, Brooklyn
Fuel & Cost
Regular Gas
$47.85 one way
$95.70 round trip
$4.11/gal25.4 MPG avg104 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.46
$51.93
$103.86
premium
$4.85
$56.46
$112.92
diesel
$4.80
$55.85
$111.71
Estimated Tolls: $16.14
Holland Tunnel
$16.00
Newark-Jersey City Turnpike
(2 mi)$0.14
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
$48
Tolls
$16
Meals
$25–$50
Total
$89–$114
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 103.5 kg one way.
Prices: EIA weekly data, 2026-07-13.
Driving Electric?
About $31 in charging
· 1 stop
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
88.7
1
$31.06
$14.20
Efficient EV
74
0
$25.88
$11.83
EV Truck/SUV
118.3
1
$41.41
$18.93
Gas CO2
103 kg
EV CO2
35 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 Jul 17, 2026
Origin
Canandaigua, NY
Late night
in Canandaigua on Monday
Local time
4:26 AM
EDT
Current temp
83°F
Areas Of Smoke
N 9 mph0% chanceLive forecast
Rip Current Statement
Rip Current Statement issued July 17 at 2:45PM EDT until July 18 at 9:00PM EDT by NWS Upton NY
Destination
Sheepshead Bay, NY
Late night
in Sheepshead Bay on Monday
Local time
4:26 AM
EDT
Current temp
86°F
Smoke
S 8 mph0% chanceLive forecast
Rip Current Statement
Rip Current Statement issued July 17 at 2:45PM EDT until July 18 at 9:00PM EDT by NWS Upton 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
3 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
6h 40m 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.
Federal Hall National Memorial
National Memorial
Here at Federal Hall, George Washington took the oath of office as the first President of the United States, marking the beginning of the American constitutional republic. This historic site served as...
0 mi from route
~1 min detour
Free
near mile 285.6
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...
1 mi from route
~1 min detour
Free
near mile 285.6
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...
1 mi from route
~1 min detour
Free
near mile 285.6
From 1794 to 1966, the U.S. Army presence on Governors Island played a vital role in the social, political, and economic life of New York City. The island then served as the headquarters of the U.S. C...
1 mi from route
~3 min detour
Free
near mile 285.6
Spanning 27,000 acres from Sandy Hook in New Jersey to Breezy Point in New York City, the park is both the gateway from the ocean into New York Harbor, and the gateway to the National Park Service for...
2 mi from route
~6 min detour
Free
near mile 295.8
A gift of friendship from the people of France to the United States "The Statue of Liberty Enlightening the World" is recognized as a universal symbol of freedom and democracy. It was dedicated by Pre...
2 mi from route
~5 min detour
Free
near mile 285.6
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
About 56% of this 295.8-mile trip is on highways, with the longest continuous interstate stretch being 73.5 miles on I 81. You'll transition from interstate cruising to surface roads, which make up the remainder of the profile. Expect a mix of faster highway travel and slower, more local road navigation as you approach your destination. This suggests you'll notice a change in speed and traffic density as you move between major roads and more populated areas.
Only 56% highway — the rest is turn-by-turn surface driving.
69 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 73.5 mi on I 81.
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 115 miles in near I 81.
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 295.8 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 115 miles (I 81): Highway fork - watch signs carefully. Lane positioning matters here; at 168.4 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 280.5 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Elevation Profile
Gently rolling terrain
1,904 ft12 ft
Total Climb
2,009 ft
Total Descent
2,792 ft
Highest Point
1,904 ft
~190.2 mi in
Elevation Range
1,891 ft
Notable High Points
1,904 ft at ~190.2 miles+799 ft prominence
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 Sheepshead Bay, NY, road signs point toward Mt Pocono, Milford, Newark and Cr 508 East: Jersey City.
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 6h 40m. Total distance: 295.8 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
6h 40m drive, plan rest stops for pacing.
Scenic Drive
Mostly surface roads route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 73.5 miles on I 81. The full list of main roads is in the Roads section above.
Expect about $16.14 in tolls one way, starting with Holland Tunnel. 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 Sheepshead Bay, 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. There are 28 rest areas along the route for bathroom stops.
The main spots that need attention: at 115 miles (I 81): Highway fork - watch signs carefully. Lane positioning matters here; at 168.4 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 280.5 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — Federal Hall National Memorial, African Burial Ground National Monument and Castle Clinton 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 6.7 hours each way, a round trip means 13.4 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Sheepshead Bay, NY before the return drive.
