Spanning 72.4 miles across Long Island, this trip from Bridgehampton to Oyster Bay typically takes about 1 hour and 46 minutes behind the wheel. Because the total duration is quite manageable, this route is perfectly suited for a single-day excursion, meaning you won’t need to worry about booking an overnight stay. You should budget approximately $12 for fuel to cover the journey. Navigating this path requires transitioning between County Road 39A, the Sunrise Highway, and the Long Island Expressway. It is a straightforward drive within the Northeast region, ideal for travelers looking to move efficiently between these two points without the need for additional stops.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
36.2 miles from Bridgehampton, NY
A natural place for your longest stop of the day
, about 54m into the drive
.
Main Roads
Road
Distance
Duration
Long Island Expressway
27.6 mi
36m
Sunrise Highway
24.2 mi
31m
County Road 39A
5.5 mi
11m
Montauk Highway
4.7 mi
9m
Horseblock Road
3.9 mi
5m
Berry Hill Road
3.7 mi
6m
Jackson Avenue
1 mi
2m
South Oyster Bay Road
0.8 mi
1m
Longest stretch:
Long Island Expressway
— 27.6 mi, about 36m
Turn-by-Turn Driving Directions
Step-by-step road directions between Bridgehampton, NY and Oyster Bay, NY.
1
Start on CR 79
67 ft·1 sec·Bridgehampton–Sag Harbor Turnpike
2
Turn right onto NY 27
4.7 mi·9 min·Montauk Highway
Use the right lane.
3
Take the exit onto NY 27
372 ft·7 sec·NY 27
Toward NY 27 West: New York
4
Merge onto NY 27; CR 39A
5.5 mi·11 min·County Road 39A
5
Continue on NY 27
24 mi·31 min·Sunrise Highway
6
Take the exit
0.1 mi·23 sec
Exit 57NToward CR 16 West: Yaphank, Horseblock RoadUse the right lane.
7
Turn left onto CR 56
0.2 mi·21 sec·Victory Avenue
8
Turn right onto CR 16
3.9 mi·5 min·Horseblock Road
Use the left lane.
9
Turn left onto Express Drive North
0.2 mi·14 sec·Express Drive North
Use the left lane.
10
Take the ramp
0.2 mi·21 sec
Toward I 495 WEST: New York
11
Merge onto I 495
28 mi·36 min·Long Island Expressway
Use the straight / slight right lanes.
12
Take the exit
0.2 mi·32 sec
Exit 43Toward South Oyster Bay Road, Bethpage, SyossetUse the slight right lane.
13
Turn straight onto North Service Road
239 ft·11 sec·North Service Road
14
Turn right onto South Oyster Bay Road
0.8 mi·1 min·South Oyster Bay Road
Use the left lane.
15
Continue on Jackson Avenue
1.0 mi·2 min·Jackson Avenue
16
Turn slight left onto Berry Hill Road
283 ft·7 sec·Berry Hill Road
Use the left lane.
17
Continue on Berry Hill Road
2.4 mi·4 min·Berry Hill Road
18
Continue on Berry Hill Road
1.2 mi·2 min·Berry Hill Road
19
Continue on Berry Hill Road
64 ft·2 sec·Berry Hill Road
20
Arrive at destination
Berry Hill Road
Trip Plan
Planning your departure is key to managing the flow of this 72.4-mile trip, as traffic patterns on the Long Island Expressway can fluctuate significantly throughout the day. Since this is a relatively short drive, you have the flexibility to depart whenever suits your schedule, though avoiding peak commuting hours is always a smart move. You won't need to plan for formal stops, but keep your $12 fuel budget in mind before you head out to ensure you have enough range for the full distance. Because you will be switching between County Road 39A and the Sunrise Highway, keep a close eye on your GPS navigation to ensure smooth transitions between these different road types. Enjoy the convenience of a trip that gets you from Bridgehampton to Oyster Bay in under two hours.
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 36.2 miles from Bridgehampton, NY, or about 54m into the drive.
The longest continuous stretch on this route runs about 27.6 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 16 miles or 28m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 36.2 miles or 54m 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 29m
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 Bridgehampton, NY so your first major turns are already loaded.
Day 1
Settle into the route from Bridgehampton, NY
This is one driving day of about 72.4 miles and 1h 46m.
Your first comfortable stop window is around 16 miles from Bridgehampton, 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 27.6 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 12
5 decision points cluster between mile 0 and 66.8 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
0 mi into trip|~0m in|NY 27 / Montauk Highway
Turn right onto NY 27 / Montauk Highway
Lane positioning matters here
Use the right lane.
8
34.4 mi into trip|~52m in
Take the exit toward CR 16 West: Yaphank, Horseblock Road
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the right lane.
Exit 57N
Toward CR 16 West: Yaphank, Horseblock Road
5
34.7 mi into trip|~52m in|CR 16 / Horseblock Road
Turn right onto CR 16 / Horseblock Road
Lane positioning matters here
Use the left lane.
8
66.6 mi into trip|~1h 35m in
Take the exit toward South Oyster Bay Road, Bethpage, Syosset
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 43
Toward South Oyster Bay Road, Bethpage, Syosset
6
66.8 mi into trip|~1h 36m in|South Oyster Bay Road
Turn right onto South Oyster Bay Road
Lane positioning matters here
Use the left lane.
Fuel & Cost
Regular Gas
$11.92 one way
$23.83 round trip
$4.18/gal25.4 MPG avg25 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$12.89
$25.77
premium
$4.92
$14.03
$28.06
diesel
$5.61
$15.99
$31.97
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$12
Meals
$25–$50
Total
$37–$62
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 25.3 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $8 in charging
· 0 stops
· 68% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
21.7
0
$7.60
$3.48
Efficient EV
18.1
0
$6.34
$2.90
EV Truck/SUV
29
0
$10.14
$4.63
Gas CO2
25 kg
EV CO2
8 kg (68% 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
Bridgehampton, NY
Late night
in Bridgehampton on Sunday
Local time
12:22 AM
EDT
Current temp
57°F
Unavailable
Live forecast
Destination
Oyster Bay, NY
Late night
in Oyster Bay on Sunday
Local time
12:22 AM
EDT
Current temp
45°F
Unavailable
Live forecast
51°F
Shirley, NY
36 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.
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
12 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 46m 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 mixed driving experience that shifts between local arteries and major thoroughfares. With 38% of your journey spent on highways, you will encounter a blend of traffic patterns as you navigate the transition from rural-leaning roads to more structured expressway travel. The longest uninterrupted stretch occurs on the Long Island Expressway, where you can settle into a 27.6-mile segment of steady driving. While the route is not a monotonous interstate grind, the variation between regional roads and high-speed lanes keeps the drive engaging. You will find that the character of the road evolves as you move from the eastern end of the island toward the north shore.
38% highway, the rest on surface roads — varied driving throughout.
20 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 27.6 mi on Long Island Expressway.
How Hard Is This Drive?
7/10
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 early in the drive near NY 27 / Montauk Highway.
Driving Effort7/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 72.4 miles you will encounter 12 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: near the start (NY 27 / Montauk Highway): Lane positioning matters here; at 34.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 34.7 miles (CR 16 / Horseblock Road): 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 Bridgehampton, NY and Oyster Bay, NY, road signs point toward Cr 16 West: Yaphank, Bethpage and Syosset.
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.
Doable as a same-day drive at 1h 46m. Total distance: 72.4 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 46m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (38%). Some complex stretches to watch for.
Scenic Drive
Mixed highway & surface route profile.
Frequently Asked Questions
The longest stretch is about 27.6 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 Oyster Bay, 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: near the start (NY 27 / Montauk Highway): Lane positioning matters here; at 34.4 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 34.7 miles (CR 16 / Horseblock Road): Lane positioning matters here.
Yes. A round trip is manageable in a single day if you plan a break at Oyster Bay, NY before heading back.
