Smithtown, NY to Pleasantville, NY is 430.6 miles and takes about 9h 13m via Christopher Columbus Highway and Long Island Expressway, with a fuel budget near $72 and enough daylight to finish in a day. This trip stays within New York, connecting two points in the Northeast region. Given the duration and distance, it's best planned as a two-day trip. Most of the route follows surface roads, so expect a more local driving experience rather than constant highway cruising. This makes it a good option if you prefer seeing more of the towns you pass through.
Trip Pace
Best split across 2 days
Treat the return leg as its own travel day rather than an afterthought.
Break Rhythm
2 planned breaks
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
215.3 miles from Smithtown, NY
A natural place for your longest stop of the day
, about 4h 22m into the drive
.
Main Roads
Road
Distance
Duration
Keystone Shortway
200 mi
3h 44m
Christopher Columbus Highway
68.2 mi
1h 20m
Long Island Expressway
24.8 mi
33m
Market Street
15.6 mi
19m
US 219
12.3 mi
18m
Montmorenci Road
8.8 mi
13m
PA 948
8.6 mi
12m
State Park Road
7.5 mi
13m
Longest stretch:
Keystone Shortway
— 200 mi, about 3h 44m
Traffic on I-80
Hour-of-day weekday pattern from 388 FHWA count stations on your route.
Peak
3 PM
~3,054 veh/hr typical
· worst 3,724
Quietest
1 AM
~358 veh/hr
Peak-to-quiet ratio
8.5×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 104 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 Pleasantville, 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
195 mi·3 hr 35 min·Keystone Shortway
32
Take the exit
0.5 mi·1 min
Toward PA 153: Clearfield, Penfield
33
Keep slight right at fork
0.2 mi·32 sec
34
Turn straight onto PA 153
7.5 mi·13 min·State Park Road
35
Continue on PA 153
5.0 mi·8 min·Hoovertown Road
36
Continue on PA 153
3.7 mi·6 min·Penfield Road
37
At end of road, turn right onto US 219
12 mi·18 min·US 219
38
Turn right onto PA 948
1.0 mi·2 min·Montmorenci Avenue
39
Continue on PA 948
8.8 mi·13 min·Montmorenci Road
40
Continue on PA 948
5.4 mi·7 min·Highland Road
41
At end of road, turn left onto PA 66
2.7 mi·3 min·Kane-Russell City Road
42
Take the exit onto PA 948
8.6 mi·12 min·PA 948
43
Continue on PA 666
2.3 mi·4 min·PA 666
44
At end of road, turn left onto US 6
1.2 mi·2 min·West Main Street
45
Continue on US 6
4.5 mi·6 min·Grand Army of the Republic Highway
46
Continue on US 6
1.4 mi·2 min·South Main Street
47
Continue on US 6
2.9 mi·4 min·Grand Army of the Republic Highway
48
Continue on US 6
0.2 mi·35 sec·Main Street
49
Continue on US 6
1.8 mi·3 min·Crescent Park
Use the straight lane.
50
Continue on Crescent Park
0.4 mi·1 min·Crescent Park
Use the right lane.
51
Turn right onto Hickory Bridge
0.1 mi·17 sec·Hickory Bridge
Use the right lane.
52
Continue on Hickory Street
0.2 mi·25 sec·Hickory Street
Use the straight / left lanes.
53
Turn right onto US 62
0.2 mi·23 sec·West 4th Avenue
54
Turn left onto US 62
16 mi·19 min·Market Street
55
At end of road, turn left onto NY 60
0.2 mi·15 sec·Foote Avenue
56
Turn right onto Martin Road
2.1 mi·3 min·Martin Road
57
Turn right onto Glenview Avenue
0.1 mi·22 sec·Glenview Avenue
58
Turn left onto West Virginia Boulevard
0.4 mi·53 sec·West Virginia Boulevard
59
Continue on Maple Street
0.4 mi·51 sec·Maple Street
60
Continue on Allen Street
0.2 mi·29 sec·Allen Street
61
Turn left onto Winsor Street
161 ft·5 sec·Winsor Street
62
Continue on this road
0.1 mi·22 sec·this road
63
Continue on Winsor Street Bridge
0.8 mi·2 min·Winsor Street Bridge
64
At end of road, turn left onto Newton Avenue
73 ft·5 sec·Newton Avenue
65
Turn right onto Lakeview Avenue
0.8 mi·1 min·Lakeview Avenue
66
Turn left onto Marvin Parkway
0.2 mi·28 sec·Marvin Parkway
67
Turn right onto NY 60
283 ft·6 sec·North Main Street
68
Keep slight left at fork onto NY 60
0.2 mi·21 sec·North Main Street
69
Keep slight right at fork onto NY 60
0.5 mi·56 sec·North Main Street
70
Merge onto I 86; NY 17
7.1 mi·8 min·Southern Tier Expressway
71
Take the exit
1.3 mi·2 min
Exit 10Toward Bemus Point
72
Turn slight right
0.2 mi·22 sec
Exit 10Toward Bemus Point, Ellery Center
73
Turn right onto Bemus-Ellery Road
467 ft·18 sec·Bemus-Ellery Road
74
Turn left onto Bayview Road
5.1 mi·8 min·Bayview Road
75
Keep slight right at fork onto Bayview Road
1.6 mi·2 min·Bayview Road
76
Turn left onto Centralia-Hartfield Road
1.7 mi·4 min·Centralia-Hartfield Road
77
Arrive at destination
Centralia-Hartfield Road
Trip Plan
For this 9h 13m drive, consider breaking it into two days to avoid fatigue. A good stopping point might be around the halfway mark, giving you roughly 4.5 hours of driving each day. With 2 recommended days, you can comfortably complete the 430.6 miles without rushing. Keep an eye on your fuel, as the estimated cost is $72, and plan your refueling stops accordingly, especially since much of the route is on surface roads. Pay attention to local speed limits as you navigate through towns and communities.
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.
This drive is better paced as a 2-day trip.
Plan roughly 2 meaningful breaks for fuel, food, and rest.
The halfway point lands around 215.3 miles from Smithtown, NY, or about 4h 22m into the drive.
The longest continuous stretch on this route runs about 200 miles.
Consider an overnight stop or starting very early.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 95 miles or 2h 4m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 215.3 miles or 4h 22m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Overnight split
Day 1 wrap after about 215.3 miles or 4h 22m
Stop before fatigue turns the last few hours into a grind. You want day two to start fresh, not just resumed.
Final approach
Final hour starts around 7h 39m
Traffic, exits, and arrival timing usually matter more near Pleasantville, 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.
+
Treat this as a 2-day road trip and book the overnight stop before the busiest arrival window.
Day 1
Settle into the route from Smithtown, NY
Aim for roughly 215 miles and 4.6 hours of wheel time on this day.
Day 2
Finish the approach into Pleasantville, NY
Aim for roughly 215 miles and 4.6 hours of wheel time on this day.
Your first comfortable stop window is around 95 miles from Smithtown, NY.
This route usually feels better as a 2-day drive than as one long push.
Plan about 2 real breaks rather than only quick fuel stops.
The longest stretch is on Keystone Shortway for about 200 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 52
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
$75.37 one way
$150.74 round trip
$4.45/gal25.4 MPG avg151 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.82
$81.68
$163.36
premium
$5.23
$88.66
$177.33
diesel
$6.18
$104.75
$209.50
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
$75
Tolls
$23
Hotel (1n)
$80–$140
Meals
$50–$100
Total
$228–$338
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 150.7 kg one way.
Prices: EIA weekly data, 2026-10-19.
Driving Electric?
About $45 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
129.2
1
$45.21
$20.67
Efficient EV
107.7
1
$37.68
$17.22
EV Truck/SUV
172.2
2
$60.28
$27.56
Gas CO2
151 kg
EV CO2
50 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 19, 2026
Origin
Smithtown, NY
Late night
in Smithtown on Wednesday
Local time
2:11 AM
EDT
Current temp
42°F
Clear
NE 3 mph0% chanceLive forecast
Destination
Pleasantville, NY
Late night
in Pleasantville on Wednesday
Local time
2:11 AM
EDT
Current temp
37°F
Clear
S 6 mph0% chanceLive forecast
56°F
Barton, NY
215 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.
For long drives, weather on day two can matter just as much as conditions at departure, so check the whole travel window rather than only the first day.
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 cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
9h 13m on the road
This is long enough that the arrival forecast matters almost as much as departure conditions. Recheck both ends before you roll.
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...
4 mi from route
~11 min detour
Free
near mile 44.5
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
~24 min detour
Free
near mile 44.5
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...
11 mi from route
~27 min detour
Free
near mile 44.5
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
~28 min detour
Free
near mile 44.5
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...
12 mi from route
~29 min detour
Free
near mile 44.5
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This route has a highway share of 18%, meaning you'll primarily be on surface roads. The longest continuous stretch on a highway is 200 miles on the Keystone Shortway. Expect frequent exits and merges as you transition between the limited highway segments and the extensive surface road network. The profile is mostly surface roads, so be prepared for varying speed limits and traffic patterns typical of local travel.
Only 18% highway — the rest is turn-by-turn surface driving.
77 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 200 mi on Keystone Shortway.
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 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 52 significant decision points across 430.6 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
Hilly terrain with moderate elevation changes
1,809 ft54 ft
Total Climb
4,066 ft
Total Descent
2,711 ft
Highest Point
1,809 ft
~369.1 mi in
Elevation Range
1,755 ft
Notable High Points
1,062 ft at ~92.3 miles+525 ft prominence
1,648 ft at ~153.8 miles+775 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 Pleasantville, 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.
Pleasantville is a village in Westchester County, New York. Downtown Pleasantville is very walkable, and has many independent restaurants, boutique shops, and grocery stores. The Jacob Burns Film Center, in the Rome Theater in downtown, was one of the first movie theaters in Westchester, and focuses primarily on independent, documentary, and world cinema.
Mostly surface roads route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 200 miles on Keystone Shortway. The full list of main roads is in the Roads section above.
Yes — a 2-day pace is more comfortable than one long haul. A sensible stopping point is after roughly 215 miles on day one.
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 38 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 Pleasantville, 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 38 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 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 9.2 hours each way, a round trip means 18.5 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Pleasantville, NY before the return drive.
