The drive from Sheepshead Bay, NY to Southold, NY covers 98.2 miles and takes about 2h 21m behind the wheel.
This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Sunrise Highway, Belt Parkway, Middle Road for much of the mileage,
and the overall profile is turn-heavy local drive.
The longest uninterrupted segment is about 60.1 miles on Sunrise Highway.
At current regular gas prices, budget about $16.16 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
49.1 miles from Sheepshead Bay, NY
A natural place for your longest stop of the day
, about 1h 10m into the drive
.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 2h 21m. Total distance: 98.2 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
2h 21m drive, comfortable solo distance.
Scenic Drive
Turn-heavy local drive route profile with national parks nearby.
Drive Character
Expect a 2h 21m drive with frequent turns across 98.2 miles of local and secondary roads.
This route has more turning and local-road decision points than a simple highway run.
There are about 20 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Sunrise Highway is the longest continuous segment at about 60.1 miles.
How Hard Is This Drive?
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. You will hit about 13 points where you need to pay attention to lane position or signs. The trickiest moment comes around 1.1 miles in near Knapp Street.
Driving Effort6/10
Moderate - straightforward overall, but long enough or busy enough to require pacing
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 98.2 miles you will encounter 13 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 1.1 miles (Knapp Street): Lane positioning matters here; at 1.2 miles: Lane positioning matters here. Multiple destination signs - pick the right one; at 1.6 miles (BP / Belt Parkway): Merge point - match speed before joining. Lane positioning matters here.
Critical Maneuvers
5 of 13 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
5
1.1 mi into trip|~3m in|Knapp Street
Turn right onto Knapp Street
Lane positioning matters here
Use the straight / right lanes.
7
1.2 mi into trip|~3m in
Turn left toward Belt Parkway East, Kennedy Airport
Lane positioning matters here. Multiple destination signs - pick the right one
Use the left lane.
Toward Belt Parkway East, Kennedy Airport
5
1.6 mi into trip|~4m in|BP / Belt Parkway
Merge onto BP / Belt Parkway
Merge point - match speed before joining. Lane positioning matters here
Use the straight / slight right lanes.
8
14.1 mi into trip|~23m in
Take the exit toward NY 27: Sunrise Highway, Brookville Boulevard
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 23B
Toward NY 27: Sunrise Highway, Brookville Boule...
6
97.6 mi into trip|~2h 19m in
Take the exit toward Southold
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the right lane.
Toward Southold
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Sheepshead Bay, NY and Southold, NY, road signs point toward Cr 31 North: Riverhead, Northville and Orient Point.
Cr 31 North: Riverhead
75.4 mi in|~1h 46m
Northville
78 mi in|~1h 50m|via CR 105
Orient Point
78 mi in|~1h 50m|via CR 105
Main Roads
Road
Distance
Duration
Sunrise Highway
60.1 mi
1h 21m
Belt Parkway
12.6 mi
18m
Middle Road
8.8 mi
12m
Sound Avenue
5.4 mi
8m
Cross River Drive
4.8 mi
6m
Quogue Riverhead Road
1.5 mi
2m
South Conduit Avenue
1 mi
1m
Old Riverhead Road
0.8 mi
1m
Longest stretch:
Sunrise Highway
— 60.1 mi, about 1h 21m
Turn-by-Turn Driving Directions
Step-by-step road directions between Sheepshead Bay, NY and Southold, NY.
1
Start on Avenue Y
0.2 mi·1 min·Avenue Y
2
Turn right onto Nostrand Avenue
0.4 mi·59 sec·Nostrand Avenue
3
Turn left onto Shore Parkway
0.4 mi·1 min·Shore Parkway
4
Turn right onto Knapp Street
451 ft·22 sec·Knapp Street
Use the straight / right lanes.
5
Turn left
0.4 mi·49 sec
Toward Belt Parkway East, Kennedy AirportUse the left lane.
6
Merge onto BP
13 mi·18 min·Belt Parkway
Use the straight / slight right lanes.
7
Take the exit
0.1 mi·22 sec
Exit 23BToward NY 27: Sunrise Highway, Brookville BoulevardUse the slight right lane.
8
Continue on NY 27
1.0 mi·1 min·South Conduit Avenue
Use the straight / right lanes.
9
Continue on NY 27
60 mi·1 hr 21 min·Sunrise Highway
Use the slight right lane.
10
Take the exit
0.3 mi·44 sec
Exit 63 NToward CR 31 North: Riverhead
11
Continue on CR 31
0.8 mi·1 min·Old Riverhead Road
12
Enter roundabout onto CR 104
161 ft·2 sec·Quogue Riverhead Road
13
Continue on CR 104
1.5 mi·2 min·Quogue Riverhead Road
14
Turn straight onto CR 105
4.8 mi·6 min·Cross River Drive
Toward Northville, Orient PointUse the right lane.
15
Turn right onto CR 43
0.5 mi·1 min·Northville Turnpike
Use the right lane.
16
Turn right onto Sound Avenue
5.4 mi·8 min·Sound Avenue
17
Continue on CR 48; Truck NY 25
8.8 mi·12 min·Middle Road
Use the left lane.
18
Take the exit
232 ft·12 sec
Toward SoutholdUse the right lane.
19
Turn slight right onto Youngs Avenue
0.5 mi·1 min·Youngs Avenue
Use the right lane.
20
Arrive at destination
Youngs Avenue
Trip Plan
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 49.1 miles from Sheepshead Bay, NY, or about 1h 10m into the drive.
The longest continuous stretch on this route runs about 60.1 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 22 miles or 34m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 49.1 miles or 1h 10m 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 53m
Traffic, exits, and arrival timing usually matter more near Southold, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Sheepshead 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.
Day 1
Settle into the route from Sheepshead Bay, NY
This is one driving day of about 98.2 miles and 2h 21m.
Your first comfortable stop window is around 22 miles from Sheepshead Bay, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on Sunrise Highway for about 60.1 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 49.1 mi from Sheepshead Bay, NY
· 1h 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.
Gateway National Recreation Area
National Recreation Area
Spanning 27,000 acres from Sandy Hook in New Jersey to Breezy Point in New York City, the park is both the gateway from the ocean into New York Harbor, and the gateway to the National Park Service for...
2 mi from route
~6 min detour
Free
Park Closure: Dead Horse Bay (Brooklyn) Remains Closed to the Public
Immerse yourself in an enchanting collage of coastal life and history. Rhythmic waves, high dunes, ancient maritime forests, historic landmarks and glimpses of wildlife, Fire Island has been a special...
6 mi from route
~14 min detour
Free
near mile 54.2
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...
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...
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...
From 1794 to 1966, the U.S. Army presence on Governors Island played a vital role in the social, political, and economic life of New York City. The island then served as the headquarters of the U.S. C...
Park data from the National Park Service API. Alerts update every 2 hours.
Fuel & Cost
Regular Gas
$16.16 one way
$32.33 round trip
$4.18/gal25.4 MPG avg34 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$17.48
$34.96
premium
$4.92
$19.03
$38.07
diesel
$5.61
$21.68
$43.36
Estimated Tolls: $0.04
Northville Turnpike
(0.5 mi)$0.04
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
$16
Tolls
$0
Meals
$25–$50
Total
$41–$66
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 34.4 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $10 in charging
· 0 stops
· 68% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
29.5
0
$10.31
$4.71
Efficient EV
24.6
0
$8.59
$3.93
EV Truck/SUV
39.3
0
$13.75
$6.28
Gas CO2
34 kg
EV CO2
11 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 15, 2026
Origin
Sheepshead Bay, NY
Afternoon
in Sheepshead Bay on Friday
Local time
4:52 PM
EDT
Current temp
50°F
Unavailable
Live forecast
Destination
Southold, NY
Afternoon
in Southold on Friday
Local time
4:52 PM
EDT
Current temp
54°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
4 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
2h 21m 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.
Frequently Asked Questions
The drive from Sheepshead Bay, NY to Southold, NY covers 98.2 miles and takes about 2h 21m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Sunrise Highway, Belt Parkway, Middle Road. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 49.1 miles from Sheepshead Bay, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $16.16 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.
This drive requires moderate attention. Across 98.2 miles you will encounter 13 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
The main spots that need attention: at 1.1 miles (Knapp Street): Lane positioning matters here; at 1.2 miles: Lane positioning matters here. Multiple destination signs - pick the right one; at 1.6 miles (BP / Belt Parkway): Merge point - match speed before joining. Lane positioning matters here.
Between Sheepshead Bay, NY and Southold, NY, road signs point toward Cr 31 North: Riverhead, Northville and Orient Point.
Yes. Nearby national parks include Gateway National Recreation Area, Fire Island National Seashore and African Burial Ground 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.
