Compiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Sep 4, 2026 · Editorial standards
Drive Time
1h 45m
Distance
70.1 mi
113 km
Drive Score
9/10
Great drive
Same Day?
Yes, doable
Fuel Cost
$12
one way
EV Charging
Unknown
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Oyster Bay, NY
Wikimedia Commons
Southold, NY
Wikimedia Commons
The drive from Oyster Bay, NY to Southold, NY covers 70.1 miles and takes about 1h 45m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Long Island Expressway, Middle Road, Sound Avenue for much of the mileage, and the overall profile is mostly highway. The longest uninterrupted segment is about 42.6 miles on Long Island Expressway. At current regular gas prices, budget about $11.76 one way before food or hotel costs.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
35 miles from Oyster Bay, NY
A natural place for your longest stop of the day , about 50m into the drive .
| Road | Distance | Duration |
|---|---|---|
| Long Island Expressway | 42.6 mi | 57m |
| Middle Road | 8.8 mi | 12m |
| Sound Avenue | 5.4 mi | 8m |
| Old Country Road | 3.1 mi | 7m |
| Northville Turnpike | 2.3 mi | 3m |
| Split Rock Road | 1.8 mi | 3m |
| Jackson Avenue | 1 mi | 2m |
| Sugar Toms Lane | 0.9 mi | 1m |
Hour-of-day weekday pattern from 32 FHWA count stations on your route.
Peak
3 PM
~4,892 veh/hr typical
Quietest
2 AM
~524 veh/hr
Peak-to-quiet ratio
9.3×
busier at peak than in the quiet hours
Averaged across 74 weeks of 2023 FHWA Travel Monitoring Analysis System data. Weekday hours only (Mon–Fri).
Step-by-step road directions between Oyster Bay, NY and Southold, NY.
Start on Berry Hill Road
Turn sharp left onto NY 106
Continue on NY 106
Turn left onto Sugar Toms Lane
Continue on Split Rock Road
Turn slight right onto Berry Hill Road
Turn straight onto Jackson Avenue
Turn left onto NY 25
Take the ramp
Merge onto NY 135
Take the exit
Merge onto I 495
Keep slight left at fork
Keep slight left at fork
Turn straight onto CR 58
Enter roundabout onto CR 58
Continue on CR 58
Turn left onto CR 43
Turn right onto Sound Avenue
Continue on CR 48; Truck NY 25
Take the exit
Turn slight right onto Youngs Avenue
Arrive at destination
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.
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 35 miles or 50m 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 Southold, NY than in the middle of the route.
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 70.1 miles and 1h 45m.
Rest stops, refuel points, and overnight suggestions along this route.
Mid-route town
Meal stop
35 mi into the route
Best for: Lunch, fuel, and a longer reset
This sits close to the middle of the route, so it works well for the longest stop of the day.
A short stop after about 15 miles helps settle the day before fatigue starts building.
The midpoint is around 35 miles from Oyster Bay, NY, which is a good place for a longer meal and fuel stop.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
5 decision points cluster between mile 0.1 and 49.8 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
Turn sharp left onto NY 106 / South Street
Sharp turn - reduce speed on approach
Turn left onto NY 25 / Jericho Turnpike
Lane positioning matters here
Take the exit toward I 495 East: Riverhead
Exit ramp - move to the correct lane early. Lane positioning matters here
Keep slight left at fork toward CR 58 East: Old Country Road, Greenport, Orient
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Keep slight left at fork toward CR 58 east: Greenport, Orient
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Regular Gas
$11.76 one way
$23.51 round trip
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.63 | $12.77 | $25.53 |
| premium | $5.05 | $13.95 | $27.89 |
| diesel | $5.60 | $15.45 | $30.90 |
Estimated Tolls: $0.16
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
$12
Tolls
$0
Meals
$25–$50
Total
$37–$62
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 24.5 kg one way. Prices: EIA weekly data, 2026-08-31.
Driving Electric?
About $7 in charging · 0 stops · 68% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 21 | 0 | $7.36 | $3.36 |
| Efficient EV | 17.5 | 0 | $6.13 | $2.80 |
| EV Truck/SUV | 28 | 0 | $9.81 | $4.49 |
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.
Current conditions at both ends of the drive.
Origin
Late night in Oyster Bay on Friday
Local time
3:35 AM
EDT
Current temp
67°F
Showers And Thunderstorms
Destination
Late night in Southold on Friday
Local time
3:35 AM
EDT
Current temp
67°F
Showers And Thunderstorms
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
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
Both ends of the route are sitting at about the same temperature right now.
Road read
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
Worth a detour if your schedule allows.
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70.1 mi in 1h 45m, mostly highway — 42.6 mi of that is on Long Island Expressway.
This is a straightforward highway drive that stays mostly on Long Island Expressway and Middle Road. 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.
Demanding - stay alert through the decision-heavy sections
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 70.1 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.
Mostly flat terrain
Total Climb
325 ft
Total Descent
346 ft
Highest Point
205 ft
~5 mi in
Elevation Range
180 ft
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Oyster Bay, NY and Southold, NY, road signs point toward Greenport, Orient, Cr 58 East: Greenport and Aquebogue.
Greenport
Orient
Cr 58 East: Greenport
Aquebogue
Founded 1667
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
Founded 1640
Southold is a town in Suffolk County, New York. It is the eastern half of Long Island's North Fork.
Top landmarks
City content from Wikivoyage (CC BY-SA 4.0) and Wikidata (CC0).
Weekend Trip
Doable as a same-day drive at 1h 45m. Total distance: 70.1 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 45m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (65%). Some complex stretches to watch for.
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, USGS 3DEP for elevation, NPS for national parks, and FHWA TMAS for hourly traffic volumes. See our methodology for refresh cadence and limitations.
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