This 409.9-mile journey from Randolph, NY, to Oyster Bay, NY, is a significant undertaking, estimated to take around 8 hours and 16 minutes of driving time. Given its length and the recommended 2-day split, it's best to plan for an overnight stop rather than attempting it as a single day trip. The primary arteries for this drive are the Southern Tier Expressway and I-81, making it a highway-focused experience across the Northeast region. With an estimated fuel cost of $67 and a plan for 2 stops, this route offers a straightforward path through New York State.
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 miles from Randolph, NY
A natural place for your longest stop of the day
, about 3h 59m into the drive
.
Drive Character
Expect a predominantly highway-focused drive, with 73% of the route utilizing major interstates. The longest uninterrupted stretch is a substantial 207.8 miles along the Southern Tier Expressway, so be prepared for extended periods of consistent speed. While largely a highway experience, the transitions between the Southern Tier Expressway, Keystone Shortway, and I-81 will offer some variation in the road's personality. This is a drive designed for covering ground efficiently.
Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 39 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Southern Tier Expressway is the longest continuous segment at about 207.8 miles.
How Hard Is This Drive?
This is a straightforward highway drive that stays mostly on Southern Tier Expressway and Keystone Shortway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 209.1 miles in near I 81.
Driving Effort9/10
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 24 significant decision points across 409.9 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 209.1 miles (I 81): Highway fork - watch signs carefully. Lane positioning matters here; at 262.5 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 377.1 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Critical Maneuvers
5 of 24 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
7
209.1 mi into trip|~4h 4m in|I 81
Keep slight right at fork onto I 81 toward I 81 South: Scranton
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight lane.
Toward I 81 South: Scranton
9
262.5 mi into trip|~5h 7m in|US 6
Keep slight right at fork onto US 6 toward I 84 East, I 380 South, US 6 East: Carbondale, Mt Pocono
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left / slight right lanes.
Exit 187
Toward I 84 East, I 380 South, US 6 East: Carbo...
8
377.1 mi into trip|~7h 23m in
Keep slight left at fork toward I 95 North: George Washington Bridge, New York City
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 95 North: George Washington Bridge, Ne...
9
377.3 mi into trip|~7h 23m in
Keep slight right at fork toward Leonia, Teaneck
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 70A-B
Toward Leonia, Teaneck
8
386.8 mi into trip|~7h 38m 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
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Randolph, NY and Oyster Bay, NY, road signs point toward Mt Pocono, Milford, New York City, Leonia, Teaneck and George Washington Bridge Upper Level.
Step-by-step road directions between Randolph, NY and Oyster Bay, NY.
1
Start on Main Street
1.0 mi·1 min·Main Street
2
Take the ramp
0.3 mi·39 sec
3
Merge onto I 86; NY 17
208 mi·4 hr 1 min·Southern Tier Expressway
4
Keep slight right at fork onto I 81
53 mi·1 hr 3 min·I 81
Toward I 81 South: ScrantonUse the straight lane.
5
Keep slight right at fork onto US 6
0.8 mi·1 min·US 6
Exit 187Toward I 84 East, I 380 South, US 6 East: Carbondale, Mt PoconoUse the slight left / slight right lanes.
6
Continue on I 84; I 380
3.7 mi·4 min·I 84; I 380
Toward I 84 East, I 380 South: Mount Pocono, MilfordUse the straight lane.
7
Keep slight right at fork onto I 380
24 mi·25 min·I 380
Exit 4Toward I 380 South: Mount Pocono
8
Keep slight left at fork
1.0 mi·1 min
Exit 1BToward I 80 East: Stroudsburg
9
Merge onto I 80
80 mi·1 hr 37 min·Keystone Shortway
Use the straight / right lanes.
10
Keep slight right at fork onto I 80
5.5 mi·5 min·Christopher Columbus Highway
Toward I 95: George Washington Bridge Lower LevelUse the slight right lane.
11
Keep slight left at fork
0.3 mi·23 sec
Toward I 95 North: George Washington Bridge, New York CityUse the straight / slight right lanes.
12
Keep slight right at fork
0.4 mi·38 sec
Exit 70A-BToward Leonia, TeaneckUse the slight right lane.
13
Turn right
0.2 mi·35 sec
Exit 70AToward LeoniaUse the straight / slight right lanes.
14
Turn straight onto CR 56
454 ft·9 sec·Degraw Avenue
15
Continue on CR 56
1.1 mi·2 min·Fort Lee Road
Use the straight / right lanes.
16
Continue on CR 56
469 ft·13 sec·Main Street
17
Take the ramp
472 ft·12 sec
Toward George Washington Bridge
18
Merge onto US 1; US 9; US 46
0.3 mi·28 sec·Bergen Boulevard
Use the straight / slight right lanes.
19
Take the exit
312 ft·4 sec
Toward George Washington Bridge Upper Level
20
Merge onto I 95 EXPR
0.3 mi·20 sec·I 95 EXPR
Use the straight / slight right lanes.
21
Keep slight left at fork onto I 95 EXPR
0.8 mi·1 min·I 95 EXPR
22
Continue on I 95; US 1; US 9
0.6 mi·1 min·George Washington Bridge (upper level)
Use the straight / slight right lanes.
23
Continue on I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
24
Continue on I 95; US 1
4.7 mi·6 min·Cross Bronx Expressway
Use the straight / slight right lanes.
25
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.
26
Merge onto I 295
0.6 mi·58 sec·Throgs Neck Expressway
27
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
Use the straight / slight right lanes.
28
Continue on I 295
2.0 mi·2 min·Clearview Expressway
Use the straight / slight right lanes.
29
Take the exit
0.2 mi·32 sec
Exit 5Toward NY 25A: Northern BoulevardUse the straight / slight right lanes.
30
Continue on Clearview Expressway
457 ft·17 sec·Clearview Expressway
31
Turn left onto NY 25A
15 mi·24 min·Northern Boulevard
Use the left lane.
32
Turn left onto NY 106
0.3 mi·29 sec·Jericho Oyster Bay Road
33
Turn straight onto NY 106
0.5 mi·46 sec·Oyster Bay Road
34
Keep slight left at fork onto NY 106
260 ft·4 sec·Oyster Bay Road
35
Continue on NY 106
0.9 mi·1 min·Pine Hollow Road
Use the left lane.
36
Continue on NY 106
105 ft·5 sec·South Street
37
Turn right onto Berry Hill Road
112 ft·9 sec·Berry Hill Road
38
Continue on Berry Hill Road
64 ft·2 sec·Berry Hill Road
39
Arrive at destination
Berry Hill Road
Trip Plan
For this 8-hour drive, consider an early morning departure to maximize daylight hours, especially if splitting it over two days. Planning your two stops strategically along the 409.9 miles will break up the driving and allow for rest. Given the longest stretch is over 200 miles, ensure you're fueled up before embarking on that segment. The estimated fuel cost of $67 is a good baseline for budgeting, but always check current prices. Breaking the drive into two days is highly recommended to avoid fatigue.
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 miles from Randolph, NY, or about 3h 59m into the drive.
The longest continuous stretch on this route runs about 207.8 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 45m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 205 miles or 3h 59m 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 miles or 3h 59m
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 6h 51m
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 Randolph, 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 Randolph, NY
Aim for roughly 205 miles and 4.1 hours of wheel time on this day.
Day 2
Finish the approach into Oyster Bay, NY
Aim for roughly 205 miles and 4.1 hours of wheel time on this day.
Your first comfortable stop window is around 90 miles from Randolph, 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 Southern Tier Expressway for about 207.8 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 205 mi from Randolph, NY
· 3h 59m into the drive
Place data sourced from public business listings. Hours and availability may vary.
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
~5 min detour
Free
near mile 381.7
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 381.7
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 381.7
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 381.7
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 381.7
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 381.7
Station data from NREL Alternative Fuel Stations database.
Driving Electric?
About $43 in charging
· 1 stop
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
123
1
$43.04
$19.68
Efficient EV
102.5
1
$35.87
$16.40
EV Truck/SUV
164
2
$57.39
$26.23
Gas CO2
143 kg
EV CO2
48 kg (66% 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 17, 2026
Origin
Randolph, NY
Night
in Randolph on Thursday
Local time
11:00 PM
EDT
Current temp
42°F
Unavailable
Live forecast
Destination
Oyster Bay, NY
Night
in Oyster Bay on Thursday
Local time
11:00 PM
EDT
Current temp
58°F
Mostly Cloudy then Slight Chance Rain Showers
SW 5 to 8 mph18% chanceLive forecast
Special Weather Statement
Special Weather Statement issued April 16 at 9:36PM EDT by NWS Albany NY
Special Weather Statement
Special Weather Statement issued April 16 at 9:03PM EDT by NWS Buffalo NY
57°F
Ramapo, NY
205 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
16 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 16m 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.
Frequently Asked Questions
The drive from Randolph, NY to Oyster Bay, NY covers 409.9 miles and takes about 8h 16m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Southern Tier Expressway, Keystone Shortway, I 81. Most of the drive stays on highways, so watch for ramps and exits.
Consider an overnight stop or starting very early.
Yes. This route is usually more comfortable as a 2-day drive. A sensible stopping point is after roughly 205 miles on day one.
The midpoint is about 205 miles from Randolph, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $67.47 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Start early — leave by 6-7 AM to arrive at a reasonable hour. This is a long drive — plan for a morning departure or consider splitting it into two days.
Plan about 2 meaningful breaks for fuel, food, or rest. Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
This is a demanding drive. With 24 significant decision points across 409.9 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.
The main spots that need attention: at 209.1 miles (I 81): Highway fork - watch signs carefully. Lane positioning matters here; at 262.5 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 377.1 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Between Randolph, NY and Oyster Bay, NY, road signs point toward Mt Pocono, Milford, New York City, Leonia, Teaneck and George Washington Bridge Upper Level.
