Trip from Oyster Bay, NY to Pleasantville, NY
Pin this tripCompiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Jul 19, 2026 · Editorial standards
Drive Time
8h 51m
Distance
411.3 mi
662 km
Drive Score
7/10
Good drive
Same Day?
2-day trip
Fuel Cost
$67
one way
EV Charging
Unknown
Best Time to Leave
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Oyster Bay, NY
Wikimedia Commons
Pleasantville, NY
Renan Tagliaferro
Trip Overview
Oyster Bay, NY to Pleasantville, NY is 411.3 miles and takes about 8h 51m via Keystone Shortway, with a fuel budget near $68 and enough daylight to finish in a day. This trip stays within the Northeast region, specifically New York, and is designed as an overnight journey with 2 recommended days. Expect a route that involves frequent turns and local driving, making it more of an exploratory drive than a direct interstate haul. It's a good option if you prefer a less predictable path and have the time to enjoy the scenery along the way.
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
205.7 miles from Oyster Bay, NY
A natural place for your longest stop of the day , about 4h 11m into the drive .
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Keystone Shortway | 200 mi | 3h 44m |
| Christopher Columbus Highway | 68.2 mi | 1h 20m |
| Market Street | 15.6 mi | 19m |
| Northern Boulevard | 13.4 mi | 22m |
| 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 |
Traffic on I-80
Hour-of-day weekday pattern from 194 FHWA count stations on your route.
Peak
3 PM
~3,076 veh/hr typical · worst 3,665
Quietest
1 AM
~346 veh/hr
Peak-to-quiet ratio
8.9×
busier at peak than in the quiet hours
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 Oyster Bay, NY and Pleasantville, NY.
Start on Berry Hill Road
Turn sharp left onto NY 106
Continue on NY 106
Continue on NY 106
Turn right onto NY 25A
Take the ramp
Merge onto CI
Take the exit
Merge onto I 295
Continue on I 295
Keep slight left at fork onto I 295
Keep slight left at fork onto I 95; US 1
Continue on I 95; US 1
Continue on I 95 EXPR; US 1 EXPR; US 9 EXPR
Keep slight left at fork onto I 95 EXPR; US 1 EXPR; US 9 EXPR
Keep slight left at fork onto I 95 EXPR; NJTP
Take the exit
Keep slight left at fork
Merge onto I 95; NJTP
Take the exit
Continue on I 80
Keep slight left at fork onto I 80
Keep slight left at fork onto I 80
Take the exit
Keep slight right at fork
Turn straight onto PA 153
Continue on PA 153
Continue on PA 153
At end of road, turn right onto US 219
Turn right onto PA 948
Continue on PA 948
Continue on PA 948
At end of road, turn left onto PA 66
Take the exit onto PA 948
Continue on PA 666
At end of road, turn left onto US 6
Continue on US 6
Continue on US 6
Continue on US 6
Continue on US 6
Continue on US 6
Continue on Crescent Park
Turn right onto Hickory Bridge
Continue on Hickory Street
Turn right onto US 62
Turn left onto US 62
At end of road, turn left onto NY 60
Turn right onto Martin Road
Turn right onto Glenview Avenue
Turn left onto West Virginia Boulevard
Continue on Maple Street
Continue on Allen Street
Turn left onto Winsor Street
Continue on this road
Continue on Winsor Street Bridge
At end of road, turn left onto Newton Avenue
Turn right onto Lakeview Avenue
Turn left onto Marvin Parkway
Turn right onto NY 60
Keep slight left at fork onto NY 60
Keep slight right at fork onto NY 60
Merge onto I 86; NY 17
Take the exit
Turn slight right
Turn right onto Bemus-Ellery Road
Turn left onto Bayview Road
Keep slight right at fork onto Bayview Road
Turn left onto Centralia-Hartfield Road
Arrive at destination
Trip Plan
Given the 8-hour 51-minute duration and its turn-heavy nature, splitting this trip over 2 days is highly recommended to avoid fatigue. Aim to depart early in the morning to maximize daylight hours for navigation. With 2 planned stops, ensure you factor in time for refueling and rest breaks, especially since the longest stretch is 200 miles. Keep a close eye on your navigation system as you'll be making frequent turns between local roads.
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.
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 90 miles or 1h 59m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 205.7 miles or 4h 11m 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 205.7 miles or 4h 11m
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 17m
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 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.
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 Oyster Bay, NY
Aim for roughly 206 miles and 4.4 hours of wheel time on this day.
Day 2
Finish the approach into Pleasantville, NY
Aim for roughly 206 miles and 4.4 hours of wheel time on this day.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Mid-route town
Overnight candidate
206 mi into the route
Best for: Hotel check-in, dinner, and a fresh start
This lines up well with a realistic day-end stop if you are breaking the drive into stages.
Find hotels in Waverly, NYOvernight Options
Night 1
206 mi · about 4.4h in
A practical overnight split lands near Waverly, NY after about 206 miles or 4.4 hours of driving.
Find hotelsPacing Suggestions
A short stop after about 90 miles helps settle the day before fatigue starts building.
The midpoint is around 205.7 miles from Oyster Bay, NY, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel checkTop up before Keystone Shortway if your tank is already low. That segment runs about 200 miles.
Overnight split
Hotel stopFor a steadier pace, wrap day one after about 206 miles or 4.4 hours on the road.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Stops Along Your Drive
Picked by where they fit in your drive — first break, midpoint reset, final stretch.
Rest Area
Montour County Rest Area Westbound
Rest area
Rest Area
Rest Area
Love's Travel Stop
TA
Pilot Travel Center
Pilot Travel Center
Crescent Lake Rest Area
Clinton County Rest Area Eastbound
Centre County Rest Area Eastbound
Luzerne County Rest Area Eastbound
TA
Service Plaza
Rest Area
Pennsylvania Welcome Center
Onvo Travel Plaza
Rest Area
Flying J Travel Center
Flying J Travel Center
Sapp Brothers Travel Center
Hickory Run Truck Plaza
Clinton County Rest Area Westbound
Montour County Rest Area Eastbound
Columbia County Rest Area Eastbound
Columbia County Rest Area Westbound
Chautauqua Lake Rest Area
TA
TA
Service Plaza
Service Plaza
Service Plaza
Onvo Travel Plaza
Blue Ridge Travel Plaza
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 465 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.
Take the ramp toward Cross Island Parkway North, Whitestone Bridge
Lane positioning matters here. Multiple destination signs - pick the right one
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
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
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
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
Fuel & Cost
Regular Gas
$66.54 one way
$133.07 round trip
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.46 | $72.20 | $144.41 |
| premium | $4.85 | $78.50 | $157.01 |
| diesel | $4.80 | $77.66 | $155.32 |
Estimated Tolls: $22.83
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
$67
Tolls
$23
Hotel (1n)
$80–$140
Meals
$50–$100
Total
$219–$329
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 143.9 kg one way. Prices: EIA weekly data, 2026-07-13.
Driving Electric?
About $43 in charging · 1 stop · 67% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 123.4 | 1 | $43.19 | $19.74 |
| Efficient EV | 102.8 | 1 | $35.99 | $16.45 |
| EV Truck/SUV | 164.5 | 2 | $57.58 | $26.32 |
Gas CO2
144 kg
EV CO2
48 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.
Origin
Oyster Bay, NY
Late night in Oyster Bay on Sunday
Local time
3:13 AM
EDT
Current temp
70°F
Smoke
Destination
Pleasantville, NY
Late night in Pleasantville on Sunday
Local time
3:13 AM
EDT
Current temp
62°F
Smoke
85°F
Waverly, NY
206 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
8 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
8h 51m 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...
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...
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...
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...
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...
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...
Park data from the National Park Service API. Alerts update every 2 hours.
What kind of drive is this?
This drive is characterized as a 'Turn-heavy local drive,' meaning you'll encounter numerous intersections and changes in direction. With only an 11% highway share, most of your time will be spent on local roads. The longest uninterrupted stretch you'll experience is 200 miles on the Keystone Shortway, offering a solid period of more consistent travel before returning to more varied local routes. Be prepared for a driving experience that requires constant attention to navigation and road conditions.
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 15.1 miles in.
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 46 significant decision points across 411.3 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.
Elevation Profile
Hilly terrain with moderate elevation changes
Total Climb
3,224 ft
Total Descent
1,862 ft
Highest Point
1,870 ft
~323.2 mi in
Elevation Range
1,824 ft
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
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 Pleasantville, NY, road signs point toward Upper Level, Njtp South: Hackensack, Hackensack and Penfield.
Upper Level
Njtp South: Hackensack
Hackensack
Penfield
About the Cities
Starting in Oyster Bay, NY
Full guide →Founded 1667
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
Arriving in Pleasantville, NY
Full guide →Founded 1695
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.
City content from Wikivoyage (CC BY-SA 4.0) and Wikidata (CC0).
Who Is This Route For?
Solo Traveler
8h 51m drive, plan rest stops for pacing.
Scenic Drive
Mostly surface roads route profile with national parks nearby.
Frequently Asked Questions
How this page is built
Compiled by the US Trip Planner planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, EIA for fuel prices, USGS 3DEP for elevation, NPS for national parks, and FHWA TMAS for hourly traffic volumes. See our methodology for refresh cadence and limitations.
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