Lenox to Smithtown is 285 miles and takes about 6 hours and 15 minutes via NY 17 and the Long Island Expressway, with a fuel budget near $46 and enough daylight to finish in a day. This trip stays within New York State, beginning in the Northeast region and ending in the same area. Most of your travel will be on highways, making it a straightforward drive. With a recommended one-day duration, this route is ideal if you're looking for an efficient way to get from point A to point B without needing an overnight stop.
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
142.3 miles from Lenox, NY
A natural place for your longest stop of the day
, about 3h 7m into the drive
.
Main Roads
Road
Distance
Duration
NY 17
106 mi
2h 12m
State Highway 8
36.8 mi
41m
Long Island Expressway
14.2 mi
19m
NJ 17
14.1 mi
18m
Northern State Parkway
13.7 mi
18m
New York State Thruway
13.7 mi
15m
State Highway 12
10.2 mi
15m
Rexford Street
8.3 mi
9m
Longest stretch:
NY 17
— 106 mi, about 2h 12m
Traffic on I-95
Hour-of-day weekday pattern from 26 FHWA count stations on your route.
Peak
7 AM
~4,026 veh/hr typical
Quietest
2 AM
~1,234 veh/hr
Peak-to-quiet ratio
3.3×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 21 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 Lenox, NY and Smithtown, NY.
1
Start on CR 54
0.2 mi·36 sec·South Court Street
2
Turn sharp left onto CR 92
0.4 mi·58 sec·Clockville Road
3
Turn right onto CR 29
0.2 mi·38 sec·Creek Road
4
Turn left onto CR 100
3.3 mi·7 min·Mount Hope Avenue
5
At end of road, turn right onto NY 46
5.6 mi·8 min·State Route 46
6
Continue on NY 46
1.0 mi·1 min·Main Street
7
Continue on NY 46
5.8 mi·7 min·Bear Path Road
8
Turn right onto NY 46
120 ft·8 sec·NY 46
9
Continue on US 20; NY 46
0.2 mi·24 sec·US 20; NY 46
10
Continue on NY 46
1.4 mi·1 min·State Route 46
11
Continue on NY 12B
2.0 mi·2 min·State Route 12B
12
Continue on NY 12B
1.1 mi·1 min·Utica Street
13
Turn slight right onto NY 12B
1.1 mi·1 min·Broad Street
14
Continue on NY 12B
4.6 mi·6 min·State Route 12B
15
Continue on NY 12B
1.4 mi·2 min·North Main Street
16
Continue on NY 12B
3.7 mi·5 min·State Highway 12B
17
Continue on NY 12B
1.4 mi·2 min·North Main Street
18
Continue on NY 12
10 mi·15 min·State Highway 12
19
Continue on NY 12
0.6 mi·1 min·North Broad Street
20
Turn left onto NY 23
8.3 mi·9 min·Rexford Street
21
Turn right onto NY 8
18 mi·20 min·State Highway 8
22
Continue on NY 8
0.4 mi·29 sec·Airport Road
23
Continue on NY 8
19 mi·21 min·State Highway 8
24
Continue on NY 8; NY 10
0.3 mi·18 sec·Oak Street
25
Continue on NY 8; NY 10
0.4 mi·44 sec·State Highway 10
26
Take the exit
0.2 mi·27 sec
Toward NY 17 East
27
Merge onto NY 17
105 mi·2 hr 11 min·NY 17
Use the straight / slight right lanes.
28
Keep slight left at fork
0.7 mi·59 sec
Toward I 87, NYST: Albany, New York CityUse the slight right lane.
29
Keep slight right at fork
0.9 mi·1 min
Toward I 87 Toll South: New York CityUse the slight right lane.
30
Merge onto I 87
14 mi·15 min·New York State Thruway
Use the straight / slight right lanes.
31
Keep slight right at fork onto NY 17
0.9 mi·59 sec·NY 17
Exit 15Toward I 287 South, NJ 17 South: New JerseyUse the slight right lane.
32
Continue on I 287; NJ 17
0.5 mi·39 sec·I 287; NJ 17
33
Keep slight left at fork onto NJ 17
14 mi·18 min·NJ 17
Exit 66Toward NJ 17 South: MahwahUse the slight left / straight lanes.
34
Take the exit
0.1 mi·19 sec
Toward NJ 4, GSP South: Paterson, Fort Lee, New York
35
Keep slight left at fork
0.5 mi·1 min
Toward NJ 4 East: Fort Lee, New York
36
Merge onto NJ 4
0.3 mi·24 sec·NJ 4
Use the right lane.
37
Continue on NJ 4
6.4 mi·8 min·NJ 4
Use the straight / slight right lanes.
38
Take the exit
0.2 mi·18 sec
Toward I 95 North: George Washington BridgeUse the straight / slight left lanes.
39
Merge onto I 95 EXPR
0.7 mi·54 sec·I 95 EXPR
Use the straight / slight right lanes.
40
Keep slight left at fork onto I 95 EXPR
0.8 mi·1 min·I 95 EXPR
41
Continue on I 95; US 1; US 9
0.6 mi·1 min·George Washington Bridge (upper level)
Use the straight / slight right lanes.
42
Continue on I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
43
Continue on I 95; US 1
4.7 mi·6 min·Cross Bronx Expressway
Use the straight / slight right lanes.
44
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.
45
Merge onto I 295
0.6 mi·58 sec·Throgs Neck Expressway
46
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
Use the straight / slight right lanes.
47
Continue on I 295
3.2 mi·3 min·Clearview Expressway
Use the straight / slight right lanes.
48
Take the exit
0.2 mi·27 sec
Exit 4E-WToward I 495: Manhattan, Eastern Long IslandUse the straight / slight right lanes.
49
Keep slight left at fork
0.3 mi·38 sec
Exit 4EToward I 495 East: Long Island Expressway, Eastern Long Island
50
Merge onto I 495
14 mi·19 min·Long Island Expressway
Use the straight / slight right lanes.
51
Take the exit
0.4 mi·52 sec
Exit 42Toward N East: HauppaugeUse the slight right lane.
52
Merge onto N
14 mi·18 min·Northern State Parkway
Use the straight / slight right lanes.
53
Take the exit
0.2 mi·25 sec
Exit 45Toward SM North: Kings ParkUse the right lane.
54
Merge onto SA
499 ft·6 sec·Sagtikos State Parkway
55
Continue on SM
1.7 mi·1 min·Sunken Meadow State Parkway
56
Take the exit
0.2 mi·30 sec
Exit SM3EToward NY 25 East: Jericho Turnpike East, SmithtownUse the slight right lane.
57
Turn slight right onto NY 25
3.9 mi·5 min·Jericho Turnpike
58
Continue on NY 25; NY 25A
0.6 mi·54 sec·West Main Street
Use the left lane.
59
Arrive at destination
NY 25; NY 25A
Trip Plan
This is a manageable one-day drive, so you have the flexibility to leave when you're ready. Aiming for an early morning departure can help you avoid potential traffic, especially as you get closer to the Long Island Expressway. With only one recommended stop, you can choose a convenient spot for a break or refuel. Keep an eye on your fuel gauge, as the longest stretch is over 100 miles, and fuel costs are estimated at $46 for this trip. Plan your final leg into Smithtown, as highway exits can become quite frequent.
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 142.3 miles from Lenox, NY, or about 3h 7m into the drive.
The longest continuous stretch on this route runs about 106 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 63 miles or 1h 31m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 142.3 miles or 3h 7m 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 3m
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 Lenox, 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 Lenox, NY
This is one driving day of about 284.7 miles and 6h 15m.
Your first comfortable stop window is around 63 miles from Lenox, 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 NY 17 for about 106 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 30
5 decision points cluster between mile 195.8 and 249.3 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
8
195.8 mi into trip|~4h 14m in
Keep slight left at fork toward I 87, NYST: Albany, New York City
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Toward I 87, NYST: Albany, New York City
9
211.1 mi into trip|~4h 33m in|NY 17
Keep slight right at fork onto NY 17 toward I 287 South, NJ 17 South: New Jersey
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 15
Toward I 287 South, NJ 17 South: New Jersey
8
212.5 mi into trip|~4h 34m in|NJ 17
Keep slight left at fork onto NJ 17 toward NJ 17 South: Mahwah
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / straight lanes.
Exit 66
Toward NJ 17 South: Mahwah
8
241.5 mi into trip|~5h 15m 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
249.3 mi into trip|~5h 25m 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
$46.06 one way
$92.11 round trip
$4.11/gal25.4 MPG avg100 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.46
$49.98
$99.96
premium
$4.85
$54.34
$108.68
diesel
$4.80
$53.76
$107.51
Estimated Tolls: $23.50
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
New York State Thruway
(13.7 mi)$0.68
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
$46
Tolls
$24
Meals
$25–$50
Total
$95–$120
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 99.6 kg one way.
Prices: EIA weekly data, 2026-07-13.
Driving Electric?
About $30 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
85.4
1
$29.89
$13.67
Efficient EV
71.2
0
$24.91
$11.39
EV Truck/SUV
113.9
1
$39.86
$18.22
Gas CO2
100 kg
EV CO2
33 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 18, 2026
Origin
Lenox, NY
Night
in Lenox on Monday
Local time
9:19 PM
EDT
Current temp
62°F
Smoke
S 1 to 7 mph4% 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
Smithtown, NY
Night
in Smithtown on Monday
Local time
9:19 PM
EDT
Current temp
70°F
Smoke
S 5 mph1% 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
8 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 15m 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...
2 mi from route
~6 min detour
Free
near mile 235.6
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
~7 min detour
Free
near mile 235.6
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
~21 min detour
Free
near mile 235.6
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...
10 mi from route
~25 min detour
Free
near mile 235.6
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...
10 mi from route
~26 min detour
Free
near mile 235.6
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...
11 mi from route
~27 min detour
Free
near mile 235.6
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect to spend about 84% of your time on highways. The longest continuous stretch without a major road change is 106 miles, primarily on NY 17. You'll experience mostly highway driving until you transition to surface roads closer to your destination. Given the predominantly highway profile, be prepared for numerous exits and potential traffic merging, especially as you approach Long Island.
84% highway — fuel and pacing are the main things to plan.
59 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 106 mi on NY 17.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on NY 17 and State Highway 8. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 195.8 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 30 significant decision points across 284.7 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 195.8 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 211.1 miles (NY 17): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 212.5 miles (NJ 17): Highway fork - watch signs carefully. Lane positioning matters here.
Elevation Profile
Gently rolling terrain
1,397 ft15 ft
Total Climb
1,634 ft
Total Descent
2,120 ft
Highest Point
1,397 ft
~142.3 mi in
Elevation Range
1,382 ft
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Lenox, NY and Smithtown, NY, road signs point toward Nyst: Albany, New York City, Gsp South: Paterson, Fort Lee, New York and Eastern Long Island - 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 6h 15m. Total distance: 284.7 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
6h 15m drive, plan rest stops for pacing.
Frequently Asked Questions
The longest stretch is about 106 miles on NY 17. The full list of main roads is in the Roads section above.
Expect about $23.50 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 9 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 1 meaningful breaks. There are 9 rest areas along the route for bathroom stops.
The main spots that need attention: at 195.8 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 211.1 miles (NY 17): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 212.5 miles (NJ 17): Highway fork - watch signs carefully. Lane positioning matters here.
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 6.3 hours each way, a round trip means 12.5 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.
