If you are looking to travel from Oyster Bay to Tuckahoe, you are in for a 66-mile journey that typically takes about 1 hour and 35 minutes. This trek is best suited as a simple one-day trip, as it is short enough to complete in a single sitting without the need for an overnight stay. You will navigate primarily via local roads like South Street, Pine Hollow Road, and Sugar Toms Lane rather than utilizing major interstates. Budgeting around $11 for fuel should cover your needs for the trip. Since both locations are situated in the Northeast, you will remain within the familiar landscape of New York for the entire duration of your drive.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
33 miles from Oyster Bay, NY
A natural place for your longest stop of the day
, about 47m into the drive
.
Main Roads
Road
Distance
Duration
Long Island Expressway
37.1 mi
50m
Sunrise Highway
13.2 mi
15m
Captain Daniel Roe Highway
4.6 mi
7m
County Road 39
3.3 mi
7m
Split Rock Road
1.8 mi
3m
Jackson Avenue
1 mi
2m
Sugar Toms Lane
0.9 mi
1m
Pine Hollow Road
0.9 mi
1m
Longest stretch:
Long Island Expressway
— 37.1 mi, about 50m
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay, NY and Tuckahoe, 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
Turn left onto Sugar Toms Lane
0.9 mi·1 min·Sugar Toms Lane
5
Continue on Split Rock Road
1.8 mi·3 min·Split Rock Road
6
Turn slight right onto Berry Hill Road
283 ft·7 sec·Berry Hill Road
7
Turn straight onto Jackson Avenue
1.0 mi·2 min·Jackson Avenue
8
Turn left onto NY 25
0.4 mi·36 sec·Jericho Turnpike
Use the left lane.
9
Take the ramp
0.3 mi·43 sec
Toward NY 135 South: Seaford
10
Merge onto NY 135
0.6 mi·37 sec·Seaford-Oyster Bay Expressway
Use the straight / slight right lanes.
11
Take the exit
0.3 mi·39 sec
Exit 13EToward I 495 East: RiverheadUse the right lane.
12
Merge onto I 495
37 mi·50 min·Long Island Expressway
Use the straight / right lanes.
13
Take the exit
0.3 mi·36 sec
Exit 70Toward CR 111: Manorville, EastportUse the straight / slight right lanes.
14
Turn right onto CR 111
4.6 mi·7 min·Captain Daniel Roe Highway
Use the right lane.
15
Take the exit
0.6 mi·49 sec
Toward NY 27 East: Montauk
16
Merge onto NY 27
13 mi·15 min·Sunrise Highway
17
Continue on NY 27; CR 39
3.3 mi·7 min·County Road 39
18
Turn slight left onto CR 52
0.1 mi·18 sec·Sandy Hollow Road
19
Turn right
330 ft·51 sec
20
Continue on this road
330 ft·30 sec·this road
21
At end of road, turn left onto CR 52
465 ft·8 sec·Sandy Hollow Road
22
Turn right onto Sebonac Road
127 ft·5 sec·Sebonac Road
Use the right lane.
23
Turn right
67 ft·4 sec
24
Arrive at destination
Trip Plan
Since this is a straightforward 66-mile drive, you have plenty of flexibility regarding your departure time. You won't need to worry about planning for multiple stops or long-distance rest breaks, as the duration is manageable for most drivers. Keep in mind that because you are sticking exclusively to local roads, traffic patterns on these specific streets can fluctuate, so check your GPS before you head out. With no formal stops programmed into the route, you can easily pull over whenever you need a breather. A great way to prepare is to ensure your fuel tank is ready for the trip, keeping that $11 estimate in mind as you head out from Oyster Bay.
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 33 miles from Oyster Bay, NY, or about 47m into the drive.
The longest continuous stretch on this route runs about 37.1 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 15 miles or 23m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 33 miles or 47m 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 18m
Traffic, exits, and arrival timing usually matter more near Tuckahoe, 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.
Day 1
Settle into the route from Oyster Bay, NY
This is one driving day of about 66 miles and 1h 35m.
Your first comfortable stop window is around 15 miles from Oyster Bay, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on Long Island Expressway for about 37.1 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 16
5 decision points cluster between mile 0.1 and 65.9 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
6
0.1 mi into trip|~0m in|NY 106 / South Street
Turn sharp left onto NY 106 / South Street
Sharp turn - reduce speed on approach
6
4.8 mi into trip|~9m in|NY 25 / Jericho Turnpike
Turn left onto NY 25 / Jericho Turnpike
Lane positioning matters here
Use the left lane.
7
6.2 mi into trip|~11m in
Take the exit toward I 495 East: Riverhead
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the right lane.
Exit 13E
Toward I 495 East: Riverhead
8
43.6 mi into trip|~1h 1m in
Take the exit toward CR 111: Manorville, Eastport
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 70
Toward CR 111: Manorville, Eastport
6
65.9 mi into trip|~1h 34m in|CR 52 / Sandy Hollow Road
At end of road, turn left onto CR 52 / Sandy Hollow Road
Complex interchange - multiple decisions in a short stretch
Fuel & Cost
Regular Gas
$10.86 one way
$21.73 round trip
$4.18/gal25.4 MPG avg23 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$11.75
$23.49
premium
$4.92
$12.79
$25.58
diesel
$5.61
$14.57
$29.14
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$11
Meals
$25–$50
Total
$36–$61
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 23.1 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $7 in charging
· 0 stops
· 65% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
19.8
0
$6.93
$3.17
Efficient EV
16.5
0
$5.77
$2.64
EV Truck/SUV
26.4
0
$9.24
$4.22
Gas CO2
23 kg
EV CO2
8 kg (65% 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 16, 2026
Origin
Oyster Bay, NY
Morning
in Oyster Bay on Sunday
Local time
6:39 AM
EDT
Current temp
45°F
Unavailable
Live forecast
Destination
Tuckahoe, NY
Morning
in Tuckahoe on Sunday
Local time
6:39 AM
EDT
Current temp
42°F
Unavailable
Live forecast
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
3 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
1h 35m 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.
More Details
What kind of drive is this?
Expect a turn-heavy local drive that keeps you engaged behind the wheel. Unlike a monotonous highway cruise, this route features zero highway miles, meaning you will be navigating local intersections and turns for the full distance. The road profile is technical, requiring your full attention as you transition between the various local thoroughfares. Because there are no long, uninterrupted stretches of open road, you should prepare for a consistent, steady pace throughout the entire 1 hour and 35 minutes. This is a hands-on driving experience that prioritizes local navigation over speed.
58% highway, the rest on surface roads — varied driving throughout.
24 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 37.1 mi on Long Island Expressway.
How Hard Is This Drive?
8/10
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 0.1 miles in near NY 106 / South Street.
Driving Effort8/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 66 miles you will encounter 16 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
Where does it get tricky?
The main spots that need attention: at 0.1 miles (NY 106 / South Street): Sharp turn - reduce speed on approach; at 4.8 miles (NY 25 / Jericho Turnpike): Lane positioning matters here; at 6.2 miles: Exit ramp - move to the correct lane early. Lane positioning matters here.
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 Tuckahoe, NY, road signs point toward Cr 111: Manorville and Eastport.
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
Doable as a same-day drive at 1h 35m. Total distance: 66 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 35m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (58%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 37.1 miles on Long Island Expressway. The full list of main roads is in the Roads section above.
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 Tuckahoe, NY before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Yes. At under 2 hours behind the wheel, this works well for families — plan one quick stop if you have younger kids.
The main spots that need attention: at 0.1 miles (NY 106 / South Street): Sharp turn - reduce speed on approach; at 4.8 miles (NY 25 / Jericho Turnpike): Lane positioning matters here; at 6.2 miles: Exit ramp - move to the correct lane early. Lane positioning matters here.
Yes. A round trip is manageable in a single day if you plan a break at Tuckahoe, NY before heading back.
