The drive from Oyster Bay, NY to Randolph, NY covers 410.4 miles and takes about 8h 19m behind the wheel.
It usually feels better as a 2-day road trip than as one long push.
The route leans on Keystone Shortway, Christopher Columbus Highway, US 219 for much of the mileage,
and the overall profile is turn-heavy local drive.
The longest uninterrupted segment is about 200 miles on Keystone Shortway.
At current regular gas prices, budget about $67.55 one way before food or hotel costs.
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
205.2 miles from Oyster Bay, NY
A natural place for your longest stop of the day
, about 4h 10m into the drive
.
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.
Turn-heavy local drive route profile with national parks nearby.
Drive Character
Expect a 8h 19m drive with frequent turns across 410.4 miles of local and secondary roads.
This route has more turning and local-road decision points than a simple highway run.
There are about 47 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Keystone Shortway is the longest continuous segment at about 200 miles.
How Hard Is This Drive?
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 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 30 significant decision points across 410.4 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.
Critical Maneuvers
5 of 30 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
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
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 Randolph, 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
Main Roads
Road
Distance
Duration
Keystone Shortway
200 mi
3h 44m
Christopher Columbus Highway
68.2 mi
1h 20m
US 219
46.5 mi
53m
Southern Tier Expressway
25.5 mi
29m
Northern Boulevard
13.4 mi
22m
Bennetts Valley Highway
10.5 mi
16m
Million Dollar Highway
8.3 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 Randolph, 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
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
Turn right onto PA 255
7.9 mi·12 min·Bennetts Valley Highway
28
Continue on PA 255
0.2 mi·20 sec·Million Dollar Highway
29
Continue on PA 255
2.6 mi·3 min·Bennetts Valley Highway
30
Turn straight onto PA 255
8.1 mi·12 min·Million Dollar Highway
31
Continue on PA 120; PA 255
0.1 mi·14 sec·South Saint Marys Street
32
Turn right onto PA 120; PA 255
147 ft·3 sec·Railroad Street
33
Turn left onto PA 120; PA 255
382 ft·8 sec·South Michael Street
34
Continue on PA 255
0.1 mi·14 sec·North Michael Street
35
Turn left onto PA 255
0.7 mi·1 min·Maurus Street
36
Continue on PA 255
4.4 mi·6 min·Johnsonburg Road
37
Continue on PA 255
2.3 mi·3 min·Johnsonburg-Saint Marys Road
38
Continue on PA 255
0.8 mi·1 min·Powers Avenue
39
Keep slight right at fork
149 ft·5 sec
40
Merge onto US 219
6.6 mi·7 min·US 219
41
Keep slight right at fork onto US 219
40 mi·44 min·US 219
42
Take the exit onto US 219
0.4 mi·46 sec·US 219
43
Merge onto I 86; US 219; NY 17
26 mi·29 min·Southern Tier Expressway
44
Take the exit
0.2 mi·29 sec
Exit 16Toward Randolph, Gowanda
45
Keep slight right at fork
170 ft·5 sec
46
Turn right onto Main Street
0.9 mi·1 min·Main Street
47
Arrive at destination
Main Street
Trip Plan
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 205.2 miles from Oyster Bay, NY, or about 4h 10m 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 205.2 miles or 4h 10m 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 205.2 miles or 4h 10m
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 9m
Traffic, exits, and arrival timing usually matter more near Randolph, 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 205 miles and 4.2 hours of wheel time on this day.
Day 2
Finish the approach into Randolph, NY
Aim for roughly 205 miles and 4.2 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.
Halfway Point
Midpoint
About 205.2 mi from Oyster Bay, NY
· 4h 10m 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...
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...
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 28.3
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 28.3
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 28.3
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 28.3
Park data from the National Park Service API. Alerts update every 2 hours.
Fuel & Cost
Regular Gas
$67.55 one way
$135.11 round trip
$4.18/gal25.4 MPG avg144 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$73.05
$146.10
premium
$4.92
$79.54
$159.09
diesel
$5.61
$90.61
$181.22
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
$220–$330
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 143.6 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
123.1
1
$43.09
$19.70
Efficient EV
102.6
1
$35.91
$16.42
EV Truck/SUV
164.2
2
$57.46
$26.27
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.
Forecast as of Apr 18, 2026
Origin
Oyster Bay, NY
Morning
in Oyster Bay on Saturday
Local time
10:42 AM
EDT
Current temp
52°F
Mostly Cloudy
NE 5 mph0% chanceLive forecast
Destination
Randolph, NY
Morning
in Randolph on Saturday
Local time
10:42 AM
EDT
Current temp
42°F
Unavailable
Live forecast
42°F
Waverly, 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
10 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 19m 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 Oyster Bay, NY to Randolph, NY covers 410.4 miles and takes about 8h 19m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Keystone Shortway, Christopher Columbus Highway, US 219. Expect a mix of highway and local road driving.
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 205.2 miles from Oyster Bay, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $67.55 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 30 significant decision points across 410.4 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.
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.
Between Oyster Bay, NY and Randolph, NY, road signs point toward Upper Level, Njtp South: Hackensack, Hackensack and Penfield.
Yes. Nearby national parks include Hamilton Grange National Memorial, General Grant National Memorial and Stonewall National Monument. There are 6 parks within detour distance of this route.
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.
