Spanning 376.4 miles across New York State, this journey from Oyster Bay to Westons Mills is a significant undertaking that requires roughly 7 hours and 40 minutes of actual driving time. Because this route avoids major highways entirely, it is a turn-heavy local drive that demands your full attention behind the wheel. Given the duration and the nature of the roads, you should budget approximately $61 for fuel to complete the trip. While it is technically possible to complete this in one day, it will be a long, demanding haul that leaves little room for error. If you prefer a more relaxed pace, consider whether you want to tackle this transit in a single push or break it up to keep your energy levels steady.
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
188.2 miles from Oyster Bay, NY
A natural place for your longest stop of the day
, about 3h 57m into the drive
.
Main Roads
Road
Distance
Duration
I 86
100 mi
1h 56m
Christopher Columbus Highway
68.2 mi
1h 20m
Southern Tier Expressway
60.6 mi
1h 10m
I 81
58.1 mi
1h 9m
I 380
27.7 mi
30m
Keystone Shortway
17.3 mi
24m
Northern Boulevard
13.4 mi
22m
Cross Bronx Expressway
6.6 mi
8m
Longest stretch:
I 86
— 100 mi, about 1h 56m
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay, NY and Westons Mills, NY.
1
Start on Berry Hill Road
288 ft·21 sec·Berry Hill Road
2
Turn sharp left onto NY 106
429 ft·9 sec·South Street
3
Continue on NY 106
0.9 mi·1 min·Pine Hollow Road
4
Continue on NY 106
0.7 mi·1 min·Oyster Bay Road
5
Turn right onto NY 25A
13 mi·22 min·Northern Boulevard
Use the left lane.
6
Take the ramp
0.2 mi·28 sec
Toward Cross Island Parkway North, Whitestone BridgeUse the right lane.
7
Merge onto CI
2.3 mi·3 min·Cross Island Parkway
Use the straight / slight right lanes.
8
Take the exit
0.6 mi·1 min
Exit 33Toward I 295 North: Throgs Neck Bridge, Bronx, New EnglandUse the straight / slight right lanes.
9
Merge onto I 295
1.8 mi·3 min·Throgs Neck Bridge
10
Continue on I 295
0.7 mi·1 min·Throgs Neck Expressway
Use the straight / slight right lanes.
11
Keep slight left at fork onto I 295
6.6 mi·8 min·Cross Bronx Expressway
Use the straight / slight right lanes.
12
Keep slight left at fork onto I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
Toward Upper Level
13
Continue on I 95; US 1
0.6 mi·59 sec·George Washington Bridge (upper level)
14
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
15
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.
16
Keep slight left at fork onto I 95 EXPR; NJTP
0.1 mi·8 sec·I 95 EXPR; NJTP
17
Take the exit
0.2 mi·22 sec
Toward I 95 South, NJTP South: HackensackUse the straight / slight right lanes.
18
Keep slight left at fork
0.4 mi·29 sec
Toward I 95 South, NJTP South: HackensackUse the slight left / slight right lanes.
19
Merge onto I 95; NJTP
2.0 mi·2 min·New Jersey Turnpike
Use the straight / slight right lanes.
20
Take the exit
0.8 mi·1 min
Exit 69Toward I 80 West: Paterson, HackensackUse the straight / slight right lanes.
21
Continue on I 80
68 mi·1 hr 20 min·Christopher Columbus Highway
Use the straight / slight right lanes.
22
Keep slight left at fork onto I 80
5.5 mi·8 min·Keystone Shortway
Use the straight / slight right lanes.
23
Keep slight left at fork onto I 80
12 mi·15 min·Keystone Shortway
24
Take the exit
0.7 mi·46 sec
Exit 293Toward I 380 North: Scranton
25
Continue on I 380
28 mi·30 min·I 380
Use the straight lane.
26
Merge onto I 81
58 mi·1 hr 9 min·I 81
Use the straight lane.
27
Keep slight left at fork onto I 86; NY 17
100 mi·1 hr 56 min·I 86; NY 17
Toward I 86: Corning
28
Keep slight right at fork onto I 86; NY 17
61 mi·1 hr 10 min·Southern Tier Expressway
Toward I 86 West, NY 17 West: Erie
29
Turn left onto State Highway 16
5.7 mi·8 min·State Highway 16
30
Continue on NY 16
1.1 mi·1 min·North Union Street
31
Enter roundabout onto NY 16
94 ft·1 sec·North Union Street
32
Continue on NY 16
0.1 mi·10 sec·North Union Street
33
Enter roundabout onto NY 16
98 ft·1 sec·North Union Street
34
Continue on NY 16
0.1 mi·12 sec·North Union Street
35
Enter roundabout onto NY 16
98 ft·1 sec·North Union Street
36
Continue on NY 16
479 ft·8 sec·North Union Street
37
Enter roundabout onto NY 16
101 ft·2 sec·North Union Street
38
Continue on NY 16
0.3 mi·23 sec·North Union Street
39
Enter roundabout onto NY 417
184 ft·4 sec·East State Street
40
Continue on NY 417
1.6 mi·2 min·East State Street
41
Continue on NY 417
1.4 mi·2 min·Olean-Portville Road
42
Arrive at destination
NY 417
Trip Plan
Planning your departure early is essential to ensure you are not navigating unfamiliar local turns after dark. With two recommended stops along the way, you should pace yourself to avoid fatigue, especially since the technical nature of these roads makes them more taxing than open highway driving. Keep a close eye on your fuel gauge, as the $61 cost estimate assumes consistent travel, and local road driving can sometimes be less fuel-efficient than highway cruising. Since you are staying entirely off the main highways, use a reliable GPS system to manage the frequent turns on Pine Hollow Road and South Street. Flexibility is your biggest advantage here, so if you find the 7-hour and 40-minute duration feels too intense, do not hesitate to build in an extra rest break to keep your driving sharp.
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 188.2 miles from Oyster Bay, NY, or about 3h 57m into the drive.
The longest continuous stretch on this route runs about 100 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 83 miles or 1h 51m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 188.2 miles or 3h 57m 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 27m
Traffic, exits, and arrival timing usually matter more near Westons Mills, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Oyster Bay, 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 Oyster Bay, NY
This is one driving day of about 376.4 miles and 7h 40m.
Your first comfortable stop window is around 83 miles from Oyster Bay, 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 86 for about 100 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 29
5 decision points cluster between mile 15.1 and 32.4 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
7
15.1 mi into trip|~25m in
Take the ramp toward Cross Island Parkway North, Whitestone Bridge
Lane positioning matters here. Multiple destination signs - pick the right one
Use the right lane.
Toward Cross Island Parkway North, Whitestone B...
8
17.6 mi into trip|~29m 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
29.8 mi into trip|~47m 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
8
30.1 mi into trip|~48m in
Keep slight left at fork toward I 95 South, NJTP South: Hackensack
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left / slight right lanes.
Toward I 95 South, NJTP South: Hackensack
8
32.4 mi into trip|~51m in
Take the exit toward I 80 West: Paterson, 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.
Exit 69
Toward I 80 West: Paterson, Hackensack
Fuel & Cost
Regular Gas
$61.96 one way
$123.92 round trip
$4.18/gal25.4 MPG avg132 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$67.00
$133.99
premium
$4.92
$72.95
$145.91
diesel
$5.61
$83.10
$166.21
Estimated Tolls: $22.83
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
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
$62
Tolls
$23
Meals
$25–$50
Total
$110–$135
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 131.7 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $40 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
112.9
1
$39.52
$18.07
Efficient EV
94.1
1
$32.93
$15.06
EV Truck/SUV
150.6
1
$52.70
$24.09
Gas CO2
132 kg
EV CO2
44 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 Apr 16, 2026
Origin
Oyster Bay, NY
Morning
in Oyster Bay on Sunday
Local time
7:57 AM
EDT
Current temp
45°F
Unavailable
Live forecast
Destination
Westons Mills, NY
Morning
in Westons Mills on Sunday
Local time
7:57 AM
EDT
Current temp
41°F
Unavailable
Live 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
4 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 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.
More Details
What kind of drive is this?
Expect a very different experience than your typical interstate cruise, as this route has a highway share of 0%. You will spend your time navigating local roads like South Street, Pine Hollow Road, and Oyster Bay Road, which prioritize navigation through smaller corridors over high-speed travel. This is a technical, turn-heavy drive that requires constant engagement rather than the monotonous rhythm of a major expressway. Since the route avoids high-speed arterials, you should anticipate a slower, more deliberate pace as you move through the Northeast landscape. Be prepared to stay alert, as the lack of highway stretches means you will be managing frequent turns and local traffic patterns for the entire duration of the trip.
71% highway — fuel and pacing are the main things to plan.
42 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 100 mi on I 86.
How Hard Is This Drive?
10/10
This is a straightforward highway drive that stays mostly on I 86 and Christopher Columbus Highway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 15.1 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 29 significant decision points across 376.4 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 15.1 miles: Lane positioning matters here. Multiple destination signs - pick the right one; at 17.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 29.8 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Oyster Bay, NY and Westons Mills, NY, road signs point toward Upper Level, Njtp South: Hackensack and Hackensack.
Oyster Bay is one of three towns in Nassau County, on Long Island, New York.
The town of Oyster Bay comprises a large portion of eastern Nassau County and includes a slew of villages and other communities. This article covers North Oyster Bay – the area closest to Oyster Bay itself (in other words, everything that is north of the Long Island Expressway). See South Oyster Bay for the southern half of the town (in other words, the area south of the expressway). See the article for Glen Cove for communities in the northwest part of the town that are closest to that city.
Top landmarks
•Christ Church — historic Episcopal parish in Oyster Bay, New York, USA
Doable as a same-day drive at 7h 40m. Total distance: 376.4 miles.
Family Friendly
Moderate complexity with 2 natural rest stops along the way.
Solo Traveler
7h 40m drive, plan rest stops for pacing.
Frequently Asked Questions
The longest stretch is about 100 miles on I 86. The full list of main roads is in the Roads section above.
Expect about $22.83 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.
We did not find dedicated rest areas on this route. For a drive this long, plan bathroom and stretch breaks around gas stations, fast-food stops, or small-town downtowns — check the Nearby Places section for options.
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 Westons Mills, 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. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 15.1 miles: Lane positioning matters here. Multiple destination signs - pick the right one; at 17.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 29.8 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Not recommended in a single day. At 7.7 hours each way, a round trip means 15.4 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Westons Mills, NY before the return drive.
