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Trip from Highland, NY to Oyster Bay, NY

Compiled and reviewed by the Trip.ovh planning team at COD Solutions Oy · Last reviewed Apr 18, 2026 · Editorial standards

Drive Time

2h 20m

Distance

101.4 mi

163 km

Drive Score

9/10

Great drive

Same Day?

Yes, doable

Fuel Cost

$17

one way

EV Charging

Unknown

Best Time to Leave

Save up to 29 min
4 AM
2h 11m ★
6 AM
2h 21m
8 AM
2h 40m
10 AM
2h 28m
12 PM
2h 26m
3 PM
2h 29m
5 PM
2h 39m
8 PM
2h 15m

Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.

Downtown Highland, NY, NY

Highland, NY

Abhishek Navlakha

town on Long Island, New York, United States

Oyster Bay, NY

Wikimedia Commons

Trip Overview

The drive from Highland, NY to Oyster Bay, NY covers 101.4 miles and takes about 2h 20m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.

The route leans on New York State Thruway, Northern Boulevard, US 9W for much of the mileage, and the overall profile is mixed highway & surface. The longest uninterrupted segment is about 29 miles on New York State Thruway. At current regular gas prices, budget about $16.69 one way before food or hotel costs.

Trip Pace

Same-day drive is realistic

A same-day return is realistic if you keep stops short.

Midpoint

50.7 miles from Highland, NY

A natural place for your longest stop of the day , about 1h 4m into the drive .

Main Roads

Road Distance Duration
New York State Thruway 29 mi 33m
Northern Boulevard 14.5 mi 24m
US 9W 14.5 mi 20m
NJ 17 14.1 mi 18m
NJ 4 6.7 mi 9m
Cross Bronx Expressway 6.6 mi 8m
Clearview Expressway 2.1 mi 2m
I 84 2 mi 2m
Longest stretch: New York State Thruway — 29 mi, about 33m

Turn-by-Turn Driving Directions

Step-by-step road directions between Highland, NY and Oyster Bay, NY.

1

Start on White Street

44 ft · 7 sec · White Street
2

Turn left onto Vineyard Avenue

0.3 mi · 51 sec · Vineyard Avenue
3

Turn left onto US 44; NY 55

0.2 mi · 32 sec · Milton Avenue
Use the left / straight / right lanes.
4

Turn right onto US 9W; US 44; NY 55

0.5 mi · 48 sec · US 9W; US 44; NY 55
Use the left / straight / right lanes.
5

Keep slight left at fork onto US 9W; US 44; NY 55

14 mi · 19 min · US 9W; US 44; NY 55
Use the straight lane.
6

Turn right onto NY 32

0.2 mi · 30 sec · North Plank Road
Use the right lane.
7

Take the ramp

0.2 mi · 32 sec
Toward I 84 West, NY 52 West Use the left lane.
8

Merge onto I 84; NY 52

2.0 mi · 2 min · I 84; NY 52
Use the straight / slight right lanes.
9

Take the exit

0.6 mi · 1 min
Exit 36A Toward I 87: New York City, Albany, New York State Thruway Use the slight right lane.
10

Continue on this road

427 ft · 10 sec · this road
11

Keep slight left at fork

0.6 mi · 40 sec
Toward I 87 South: New York City
12

Merge onto I 87

29 mi · 33 min · New York State Thruway
Use the straight / slight right lanes.
13

Keep slight right at fork onto NY 17

0.9 mi · 59 sec · NY 17
Exit 15 Toward I 287 South, NJ 17 South: New Jersey Use the slight right lane.
14

Continue on I 287; NJ 17

0.5 mi · 39 sec · I 287; NJ 17
15

Keep slight left at fork onto NJ 17

14 mi · 18 min · NJ 17
Exit 66 Toward NJ 17 South: Mahwah Use the slight left / straight lanes.
16

Take the exit

0.1 mi · 19 sec
Toward NJ 4, GSP South: Paterson, Fort Lee, New York
17

Keep slight left at fork

0.5 mi · 1 min
Toward NJ 4 East: Fort Lee, New York
18

Merge onto NJ 4

0.3 mi · 24 sec · NJ 4
Use the right lane.
19

Continue on NJ 4

6.4 mi · 8 min · NJ 4
Use the straight / slight right lanes.
20

Take the exit

0.2 mi · 18 sec
Toward I 95 North: George Washington Bridge Use the straight / slight left lanes.
21

Merge onto I 95 EXPR

0.7 mi · 54 sec · I 95 EXPR
Use the straight / slight right lanes.
22

Keep slight left at fork onto I 95 EXPR

0.8 mi · 1 min · I 95 EXPR
23

Continue on I 95; US 1; US 9

0.6 mi · 1 min · George Washington Bridge (upper level)
Use the straight / slight right lanes.
24

Continue on I 95; US 1

0.7 mi · 1 min · Trans-Manhattan Expressway
25

Continue on I 95; US 1

4.7 mi · 6 min · Cross Bronx Expressway
Use the straight / slight right lanes.
26

Keep slight right at fork onto I 295

2.0 mi · 2 min · Cross Bronx Expressway
Exit 6B Toward I 295 South: Throgs Neck Bridge Use the straight / slight left lanes.
27

Merge onto I 295

0.6 mi · 58 sec · Throgs Neck Expressway
28

Continue on I 295

2.0 mi · 3 min · Throgs Neck Bridge
Use the straight / slight right lanes.
29

Continue on I 295

2.0 mi · 2 min · Clearview Expressway
Use the straight / slight right lanes.
30

Take the exit

0.2 mi · 32 sec
Exit 5 Toward NY 25A: Northern Boulevard Use the straight / slight right lanes.
31

Continue on Clearview Expressway

457 ft · 17 sec · Clearview Expressway
32

Turn left onto NY 25A

15 mi · 24 min · Northern Boulevard
Use the left lane.
33

Turn left onto NY 106

0.3 mi · 29 sec · Jericho Oyster Bay Road
34

Turn straight onto NY 106

0.5 mi · 46 sec · Oyster Bay Road
35

Keep slight left at fork onto NY 106

260 ft · 4 sec · Oyster Bay Road
36

Continue on NY 106

0.9 mi · 1 min · Pine Hollow Road
Use the left lane.
37

Continue on NY 106

105 ft · 5 sec · South Street
38

Turn right onto Berry Hill Road

112 ft · 9 sec · Berry Hill Road
39

Continue on Berry Hill Road

64 ft · 2 sec · Berry Hill Road
40

Arrive at destination

Berry Hill Road

Trip Plan

Morning Departure

Leave by 9 AM and you'll arrive before lunch.

Evening Departure

Even a 4 PM departure gets you there before dark in summer.

You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 50.7 miles from Highland, NY, or about 1h 4m into the drive.
The longest continuous stretch on this route runs about 29 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 22 miles or 31m in

Use this first pause for coffee, a restroom break, and a quick traffic check ahead.

Halfway reset

Around 50.7 miles or 1h 4m in

This is the best place for your longest stop, a real meal, and a full fuel check.

Final approach

Final hour starts around 1h 50m

Traffic, exits, and arrival timing usually matter more near Oyster Bay, NY than in the middle of the route.

Before You Leave

+

Open the route before leaving Highland, 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 Highland, NY

This is one driving day of about 101.4 miles and 2h 20m.

Your first comfortable stop window is around 22 miles from Highland, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on New York State Thruway for about 29 miles.

Where to Stop

Rest stops, refuel points, and overnight suggestions along this route.

town in Rockland County, New York, United States

Mid-route town

Meal stop

Ramapo, NY

51 mi into the route

Best for: Lunch, fuel, and a longer reset

This sits close to the middle of the route, so it works well for the longest stop of the day.

Pacing Suggestions

New Windsor, NY

Fuel and coffee

A short stop after about 22 miles helps settle the day before fatigue starts building.

Ramapo, NY

Meal break

The midpoint is around 50.7 miles from Highland, NY, which is a good place for a longer meal and fuel stop.

These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.

Heads-up: tricky spots

5 of 25

5 decision points cluster between mile 15.2 and 78.3 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.

8
15.2 mi into trip | ~22m in

Take the ramp toward I 84 West, NY 52 West

Lane positioning matters here. Multiple destination signs - pick the right one

Use the left lane. Toward I 84 West, NY 52 West
8
17.5 mi into trip | ~25m in

Take the exit toward I 87: New York City, Albany, New York State Thruway

Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one

Use the slight right lane. Exit 36A Toward I 87: New York City, Albany, New York St...
9
47.8 mi into trip | ~1h 1m 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
49.2 mi into trip | ~1h 2m 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
78.3 mi into trip | ~1h 42m 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

Fuel & Cost

Regular Gas

$16.69 one way

$33.38 round trip

$4.18/gal 25.4 MPG avg 36 kg CO2
Fuel Type $/gal One Way Round Trip
midgrade $4.52 $18.05 $36.10
premium $4.92 $19.65 $39.31
diesel $5.61 $22.39 $44.78

Estimated Tolls: $24.00

George Washington Bridge $16.00
Throgs Neck Bridge $6.55
New York State Thruway (29 mi) $1.45

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

$17

Tolls

$24

Meals

$25–$50

Total

$66–$91

Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.

Estimated CO2 emission: 35.5 kg one way. Prices: EIA weekly data, 2026-04-13.

Driving Electric?

About $11 in charging · 0 stops · 66% less CO2

Vehicle Type kWh Stops DC Fast Home Charge
Average EV 30.4 0 $10.65 $4.87
Efficient EV 25.4 0 $8.87 $4.06
EV Truck/SUV 40.6 0 $14.20 $6.49

Gas CO2

35 kg

EV CO2

12 kg (66% less)

This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.

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 18, 2026

Origin

Highland, NY

Afternoon in Highland on Saturday

Local time

1:28 PM

EDT

Current temp

44°F

Unavailable

Live forecast

Destination

Oyster Bay, NY

Afternoon in Oyster Bay on Saturday

Local time

1:28 PM

EDT

Current temp

45°F

Unavailable

Live forecast

49°F

Ramapo, NY

51 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.

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

1 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

2h 20m on the road

Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.

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

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 ~5 min detour Free near mile 73.4
View on nps.gov
General Grant National Memorial

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 ~7 min detour Free near mile 73.4
View on nps.gov
Stonewall National Monument

Stonewall National Monument

National Monument

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 73.4
View on nps.gov
African Burial Ground National Monument

African Burial Ground National Monument

National Monument

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 73.4
View on nps.gov
Federal Hall National Memorial

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...

10 mi from route ~26 min detour Free near mile 73.4
View on nps.gov
Castle Clinton National Monument

Castle Clinton National Monument

National Monument

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 73.4
View on nps.gov

Park data from the National Park Service API. Alerts update every 2 hours.

What kind of drive is this?

101.4 mi in 2h 20m — 50% highway, the rest on surface roads. Biggest road: New York State Thruway.

50% highway, the rest on surface roads — varied driving throughout.
40 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 29 mi on New York State Thruway.

How Hard Is This Drive?

10/10

This route mixes highway mileage with some local-road sections near the start or finish. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 15.2 miles in.

Driving Effort 10/10

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 25 significant decision points across 101.4 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 15.2 miles: Lane positioning matters here. Multiple destination signs - pick the right one; at 17.5 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 47.8 miles (NY 17): Highway fork - watch signs carefully. 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 Highland, NY and Oyster Bay, NY, road signs point toward Albany, New York State Thruway, Gsp South: Paterson, Fort Lee and New York.

Albany

17.5 mi in | ~25m

New York State Thruway

17.5 mi in | ~25m

Gsp South: Paterson

63.3 mi in | ~1h 21m

Fort Lee

63.3 mi in | ~1h 21m

New York

63.3 mi in | ~1h 21m

About the Cities

Arriving in Oyster Bay, NY

Full guide →

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.

City content from Wikivoyage (CC BY-SA 4.0) and Wikidata (CC0).

Who Is This Route For?

Weekend Trip

Doable as a same-day drive at 2h 20m. Total distance: 101.4 miles.

Family Friendly

Moderate complexity with 0 natural rest stops along the way.

Solo Traveler

2h 20m drive, comfortable solo distance.

First-Time Driver

Mostly highway driving (50%). Some complex stretches to watch for.

Scenic Drive

Mixed highway & surface route profile with national parks nearby.

Frequently Asked Questions

The longest stretch is about 29 miles on New York State Thruway. The full list of main roads is in the Roads section above.

Expect about $24.00 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.

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 Oyster 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. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.

The main spots that need attention: at 15.2 miles: Lane positioning matters here. Multiple destination signs - pick the right one; at 17.5 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 47.8 miles (NY 17): 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.

Yes. A round trip is manageable in a single day if you plan a break at Oyster Bay, NY before heading back.

How this page is built

Compiled by the Trip.ovh planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, EIA for fuel prices, and NPS for national parks. See our methodology for refresh cadence and limitations.

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