Origin
Oyster Bay, NY
Late night in Oyster Bay on Sunday
Local time
12:58 AM
EDT
Current temp
45°F
Unavailable
Live forecast
Trip from Oyster Bay, NY to Pleasantville, NY
Compiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Apr 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
$68
one way
EV Charging
Unknown
Best Time to Leave
4 AM
8h 44m
★
6 AM
8h 52m
8 AM
9h 8m
10 AM
8h 58m
12 PM
8h 56m
3 PM
8h 58m
5 PM
9h 7m
8 PM
8h 47m
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 |
Longest stretch:
Keystone Shortway
— 200 mi, about 3h 44m
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay, NY and Pleasantville, 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 Bridge
Use 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 33
Toward I 295 North: Throgs Neck Bridge, Bronx, New England
Use 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: Hackensack
Use the straight / slight right lanes.
18
Keep slight left at fork
0.4 mi
·
29 sec
Toward I 95 South, NJTP South: Hackensack
Use 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 69
Toward I 80 West: Paterson, Hackensack
Use 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
195 mi
·
3 hr 35 min
·
Keystone Shortway
24
Take the exit
0.5 mi
·
1 min
Toward PA 153: Clearfield, Penfield
25
Keep slight right at fork
0.2 mi
·
32 sec
26
Turn straight onto PA 153
7.5 mi
·
13 min
·
State Park Road
27
Continue on PA 153
5.0 mi
·
8 min
·
Hoovertown Road
28
Continue on PA 153
3.7 mi
·
6 min
·
Penfield Road
29
At end of road, turn right onto US 219
12 mi
·
18 min
·
US 219
30
Turn right onto PA 948
1.0 mi
·
2 min
·
Montmorenci Avenue
31
Continue on PA 948
8.8 mi
·
13 min
·
Montmorenci Road
32
Continue on PA 948
5.4 mi
·
7 min
·
Highland Road
33
At end of road, turn left onto PA 66
2.7 mi
·
3 min
·
Kane-Russell City Road
34
Take the exit onto PA 948
8.6 mi
·
12 min
·
PA 948
35
Continue on PA 666
2.3 mi
·
4 min
·
PA 666
36
At end of road, turn left onto US 6
1.2 mi
·
2 min
·
West Main Street
37
Continue on US 6
4.5 mi
·
6 min
·
Grand Army of the Republic Highway
38
Continue on US 6
1.4 mi
·
2 min
·
South Main Street
39
Continue on US 6
2.9 mi
·
4 min
·
Grand Army of the Republic Highway
40
Continue on US 6
0.2 mi
·
35 sec
·
Main Street
41
Continue on US 6
1.8 mi
·
3 min
·
Crescent Park
Use the straight lane.
42
Continue on Crescent Park
0.4 mi
·
1 min
·
Crescent Park
Use the right lane.
43
Turn right onto Hickory Bridge
0.1 mi
·
17 sec
·
Hickory Bridge
Use the right lane.
44
Continue on Hickory Street
0.2 mi
·
25 sec
·
Hickory Street
Use the straight / left lanes.
45
Turn right onto US 62
0.2 mi
·
23 sec
·
West 4th Avenue
46
Turn left onto US 62
16 mi
·
19 min
·
Market Street
47
At end of road, turn left onto NY 60
0.2 mi
·
15 sec
·
Foote Avenue
48
Turn right onto Martin Road
2.1 mi
·
3 min
·
Martin Road
49
Turn right onto Glenview Avenue
0.1 mi
·
22 sec
·
Glenview Avenue
50
Turn left onto West Virginia Boulevard
0.4 mi
·
53 sec
·
West Virginia Boulevard
51
Continue on Maple Street
0.4 mi
·
51 sec
·
Maple Street
52
Continue on Allen Street
0.2 mi
·
29 sec
·
Allen Street
53
Turn left onto Winsor Street
161 ft
·
5 sec
·
Winsor Street
54
Continue on this road
0.1 mi
·
22 sec
·
this road
55
Continue on Winsor Street Bridge
0.8 mi
·
2 min
·
Winsor Street Bridge
56
At end of road, turn left onto Newton Avenue
73 ft
·
5 sec
·
Newton Avenue
57
Turn right onto Lakeview Avenue
0.8 mi
·
1 min
·
Lakeview Avenue
58
Turn left onto Marvin Parkway
0.2 mi
·
28 sec
·
Marvin Parkway
59
Turn right onto NY 60
283 ft
·
6 sec
·
North Main Street
60
Keep slight left at fork onto NY 60
0.2 mi
·
21 sec
·
North Main Street
61
Keep slight right at fork onto NY 60
0.5 mi
·
56 sec
·
North Main Street
62
Merge onto I 86; NY 17
7.1 mi
·
8 min
·
Southern Tier Expressway
63
Take the exit
1.3 mi
·
2 min
Exit 10
Toward Bemus Point
64
Turn slight right
0.2 mi
·
22 sec
Exit 10
Toward Bemus Point, Ellery Center
65
Turn right onto Bemus-Ellery Road
467 ft
·
18 sec
·
Bemus-Ellery Road
66
Turn left onto Bayview Road
5.1 mi
·
8 min
·
Bayview Road
67
Keep slight right at fork onto Bayview Road
1.6 mi
·
2 min
·
Bayview Road
68
Turn left onto Centralia-Hartfield Road
1.7 mi
·
4 min
·
Centralia-Hartfield Road
69
Arrive at destination
Centralia-Hartfield Road
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.
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 205.7 miles from Oyster Bay, NY, or about 4h 11m 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 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.
Your first comfortable stop window is around 90 miles from Oyster Bay, 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.
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
Fuel and coffee
A short stop after about 90 miles helps settle the day before fatigue starts building.
Meal break
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.
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.
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
$67.70 one way
$135.41 round trip
$4.18/gal
25.4 MPG avg
144 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.52 | $73.21 | $146.42 |
| premium | $4.92 | $79.72 | $159.44 |
| diesel | $5.61 | $90.81 | $181.62 |
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
$68
Tolls
$23
Hotel (1n)
$80–$140
Meals
$50–$100
Total
$221–$331
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, 2026-04-13.
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.
Destination
Pleasantville, NY
Late night in Pleasantville on Sunday
Local time
12:58 AM
EDT
Current temp
49°F
Unavailable
Live forecast
48°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
4 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
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...
2 mi from route
~6 min detour
Free
near mile 28.4
View on nps.gov
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 28.4
View on nps.gov
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 28.4
View on nps.gov
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 28.4
View on nps.gov
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 28.4
View on nps.gov
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 28.4
View on nps.gov
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.
Only 11% highway — the rest is turn-by-turn surface driving.
69 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 15.1 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 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.
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
27.3 mi in
|
~43m
|
via I 95; US 1
Njtp South: Hackensack
29.8 mi in
|
~47m
Hackensack
32.4 mi in
|
~51m
Penfield
301.4 mi in
|
~5h 57m
About the Cities
Starting 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.
Arriving in Pleasantville, NY
Full guide →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
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 206 miles on day one.
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 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. 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.
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 8.9 hours each way, a round trip means 17.7 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.
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, and NPS for national parks. See our methodology for refresh cadence and limitations.
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