Webster, NY to Smithtown, NY is 370.2 miles and takes about 7h 47m via I 81 and Irondequoit–Wayne County Expressway, with a fuel budget near $60 and enough daylight to finish in a day. This trip stays within New York, traversing the Northeast region from western to central parts of the state. Expect a predominantly highway experience, making it a straightforward drive for a single day. The route offers a direct path, ideal if you're looking for efficiency and a no-frills transit 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
2 planned breaks
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
185.1 miles from Webster, NY
A natural place for your longest stop of the day
, about 3h 55m into the drive
.
Main Roads
Road
Distance
Duration
I 81
128.7 mi
2h 32m
Keystone Shortway
80 mi
1h 37m
Irondequoit–Wayne County Expressway
34.3 mi
47m
I 380
23.6 mi
25m
Long Island Expressway
14.2 mi
19m
Northern State Parkway
13.7 mi
18m
I 690
8.7 mi
10m
State Highway 370
7.9 mi
10m
Longest stretch:
I 81
— 128.7 mi, about 2h 32m
Traffic on I-80
Hour-of-day weekday pattern from 168 FHWA count stations on your route.
Peak
3 PM
~4,210 veh/hr typical
· worst 4,900
Quietest
1 AM
~430 veh/hr
Peak-to-quiet ratio
9.8×
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 Webster, NY and Smithtown, NY.
1
Start on NY 404
91 ft·7 sec·East Main Street
2
Turn right onto NY 250
0.2 mi·23 sec·North Avenue
3
Take the ramp
0.2 mi·20 sec
Toward NY 104 East
4
Merge onto NY 104
34 mi·47 min·Irondequoit–Wayne County Expressway
5
Turn right onto CR 163
2.2 mi·2 min·Ridge Road
6
Turn slight right onto NY 370
2.1 mi·2 min·State Route 370
7
Continue on NY 370
7.9 mi·10 min·State Highway 370
8
Continue on NY 370
3.6 mi·7 min·West Main Street
9
Continue on NY 370
1.7 mi·2 min·State Route 370
10
Continue on NY 370
0.7 mi·53 sec·Main Street
11
Continue on NY 370
5.7 mi·8 min·West Genesee Road
Use the left / straight lanes.
12
Take the exit onto NY 31
5.9 mi·7 min·NY 31
Use the left lane.
13
Continue on I 690
8.7 mi·10 min·I 690
Use the straight / slight right lanes.
14
Take the exit
0.2 mi·30 sec
Toward I 81 South: BinghamtonUse the straight / slight right lanes.
15
Merge onto I 81
2.8 mi·4 min·I 81
Use the straight / slight right lanes.
16
Continue on I-81
0.8 mi·48 sec·I-81
17
Continue on I 81
73 mi·1 hr 25 min·I 81
Use the straight / slight right lanes.
18
Keep slight right at fork onto I 81
53 mi·1 hr 3 min·I 81
Toward I 81 South: ScrantonUse the straight lane.
19
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.
20
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.
21
Keep slight right at fork onto I 380
24 mi·25 min·I 380
Exit 4Toward I 380 South: Mount Pocono
22
Keep slight left at fork
1.0 mi·1 min
Exit 1BToward I 80 East: Stroudsburg
23
Merge onto I 80
80 mi·1 hr 37 min·Keystone Shortway
Use the straight / right lanes.
24
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.
25
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.
26
Keep slight right at fork
0.4 mi·38 sec
Exit 70A-BToward Leonia, TeaneckUse the slight right lane.
27
Turn right
0.2 mi·35 sec
Exit 70AToward LeoniaUse the straight / slight right lanes.
28
Turn straight onto CR 56
454 ft·9 sec·Degraw Avenue
29
Continue on CR 56
1.1 mi·2 min·Fort Lee Road
Use the straight / right lanes.
30
Continue on CR 56
469 ft·13 sec·Main Street
31
Take the ramp
472 ft·12 sec
Toward George Washington Bridge
32
Merge onto US 1; US 9; US 46
0.3 mi·28 sec·Bergen Boulevard
Use the straight / slight right lanes.
33
Take the exit
312 ft·4 sec
Toward George Washington Bridge Upper Level
34
Merge onto I 95 EXPR
0.3 mi·20 sec·I 95 EXPR
Use the straight / slight right lanes.
35
Keep slight left at fork onto I 95 EXPR
0.8 mi·1 min·I 95 EXPR
36
Continue on I 95; US 1; US 9
0.6 mi·1 min·George Washington Bridge (upper level)
Use the straight / slight right lanes.
37
Continue on I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
38
Continue on I 95; US 1
4.7 mi·6 min·Cross Bronx Expressway
Use the straight / slight right lanes.
39
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.
40
Merge onto I 295
0.6 mi·58 sec·Throgs Neck Expressway
41
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
Use the straight / slight right lanes.
42
Continue on I 295
3.2 mi·3 min·Clearview Expressway
Use the straight / slight right lanes.
43
Take the exit
0.2 mi·27 sec
Exit 4E-WToward I 495: Manhattan, Eastern Long IslandUse the straight / slight right lanes.
44
Keep slight left at fork
0.3 mi·38 sec
Exit 4EToward I 495 East: Long Island Expressway, Eastern Long Island
45
Merge onto I 495
14 mi·19 min·Long Island Expressway
Use the straight / slight right lanes.
46
Take the exit
0.4 mi·52 sec
Exit 42Toward N East: HauppaugeUse the slight right lane.
47
Merge onto N
14 mi·18 min·Northern State Parkway
Use the straight / slight right lanes.
48
Take the exit
0.2 mi·25 sec
Exit 45Toward SM North: Kings ParkUse the right lane.
49
Merge onto SA
499 ft·6 sec·Sagtikos State Parkway
50
Continue on SM
1.7 mi·1 min·Sunken Meadow State Parkway
51
Take the exit
0.2 mi·30 sec
Exit SM3EToward NY 25 East: Jericho Turnpike East, SmithtownUse the slight right lane.
52
Turn slight right onto NY 25
3.9 mi·5 min·Jericho Turnpike
53
Continue on NY 25; NY 25A
0.6 mi·54 sec·West Main Street
Use the left lane.
54
Arrive at destination
NY 25; NY 25A
Trip Plan
Given the 7h 47m estimated drive time, departing in the morning is recommended to ensure you have ample daylight. With two planned stops, you can easily break up the 370.2 miles into manageable segments. The longest stretch without a significant break is 128.7 miles on I 81, so plan your first stop after this section. Keep an eye on your fuel gauge, especially during the longer highway portions, as the estimated cost is $60. This drive is well within the capabilities of a single day, offering flexibility in your timing and stop duration.
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 185.1 miles from Webster, NY, or about 3h 55m into the drive.
The longest continuous stretch on this route runs about 128.7 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 81 miles or 1h 52m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 185.1 miles or 3h 55m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 6h 24m
Traffic, exits, and arrival timing usually matter more near Smithtown, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Webster, 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 Webster, NY
This is one driving day of about 370.2 miles and 7h 47m.
Your first comfortable stop window is around 81 miles from Webster, 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 128.7 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 32
5 decision points cluster between mile 202.8 and 334.8 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
9
202.8 mi into trip|~4h 16m 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
317.3 mi into trip|~6h 32m 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
317.6 mi into trip|~6h 32m 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
327 mi into trip|~6h 46m 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
8
334.8 mi into trip|~6h 57m in
Take the exit toward I 495: Manhattan, Eastern Long Island
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 4E-W
Toward I 495: Manhattan, Eastern Long Island
Fuel & Cost
Regular Gas
$59.89 one way
$119.78 round trip
$4.11/gal25.4 MPG avg130 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.46
$64.99
$129.98
premium
$4.85
$70.66
$141.32
diesel
$4.80
$69.90
$139.80
Estimated Tolls: $22.82
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
Jericho Turnpike
(3.9 mi)$0.27
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
$60
Tolls
$23
Meals
$25–$50
Total
$108–$133
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 129.5 kg one way.
Prices: EIA weekly data, 2026-07-13.
Driving Electric?
About $39 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
111.1
1
$38.87
$17.77
Efficient EV
92.6
1
$32.39
$14.81
EV Truck/SUV
148.1
1
$51.83
$23.69
Gas CO2
130 kg
EV CO2
43 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 Jul 17, 2026
Origin
Webster, NY
Morning
in Webster on Sunday
Local time
11:25 AM
EDT
Current temp
65°F
Patchy Smoke
NE 3 mph0% chanceLive forecast
Destination
Smithtown, NY
Morning
in Smithtown on Sunday
Local time
11:25 AM
EDT
Current temp
70°F
Smoke
N 5 mph0% chanceLive forecast
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
5 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 47m 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.
General Grant National Memorial
National Memorial
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...
3 mi from route
~9 min detour
Free
near mile 319.1
Caution: Lower Crypt Access Subject to Safe Conditions
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
~9 min detour
Free
near mile 319.1
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
~22 min detour
Free
near mile 319.1
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
~25 min detour
Free
near mile 319.1
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
~27 min detour
Free
near mile 319.1
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...
11 mi from route
~27 min detour
Free
near mile 319.1
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 71% of the 370.2 miles spent on major roads. You'll encounter a long stretch of 128.7 miles on I 81, offering sustained cruising. The remainder of the drive will transition to surface roads like the Irondequoit–Wayne County Expressway, which will likely feature more varied speed limits and closer exits as you approach your destination.
71% highway — fuel and pacing are the main things to plan.
54 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 128.7 mi on I 81.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on I 81 and Keystone Shortway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 202.8 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 32 significant decision points across 370.2 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 202.8 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 317.3 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 317.6 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Elevation Profile
Gently rolling terrain
1,819 ft54 ft
Total Climb
2,021 ft
Total Descent
2,415 ft
Highest Point
1,819 ft
~211.5 mi in
Elevation Range
1,765 ft
Notable High Points
1,819 ft at ~211.5 miles+695 ft prominence
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Webster, NY and Smithtown, NY, road signs point toward Mt Pocono, Milford, New York City, Leonia, Teaneck and George Washington Bridge Upper Level - 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.
Doable as a same-day drive at 7h 47m. Total distance: 370.2 miles.
Family Friendly
Moderate complexity with 2 natural rest stops along the way.
Solo Traveler
7h 47m drive, plan rest stops for pacing.
Frequently Asked Questions
The longest stretch is about 128.7 miles on I 81. The full list of main roads is in the Roads section above.
Expect about $22.82 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 29 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 Smithtown, 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 29 rest areas along the route for bathroom stops.
The main spots that need attention: at 202.8 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 317.3 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 317.6 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — General Grant National Memorial, Hamilton Grange National Memorial and Stonewall 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 7.8 hours each way, a round trip means 15.6 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Smithtown, NY before the return drive.
