The drive from Tonawanda, NY to Southold, NY covers 471.5 miles and takes about 10h 4m behind the wheel.
It usually feels better as a 2-day road trip than as one long push.
The route leans on New York State Thruway, I 81, Keystone Shortway for much of the mileage,
and the overall profile is turn-heavy local drive.
The longest uninterrupted segment is about 99.4 miles on New York State Thruway.
At current regular gas prices, budget about $77.61 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
235.7 miles from Tonawanda, NY
A natural place for your longest stop of the day
, about 4h 59m into the drive
.
Who Is This Route For?
Solo Traveler
10h 4m drive, plan rest stops for pacing.
Scenic Drive
Turn-heavy local drive route profile with national parks nearby.
Drive Character
Expect a 10h 4m drive with frequent turns across 471.5 miles of local and secondary roads.
This route has more turning and local-road decision points than a simple highway run.
There are about 68 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
New York State Thruway is the longest continuous segment at about 99.4 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 8.8 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 47 significant decision points across 471.5 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 8.8 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 108.9 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 259.1 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Critical Maneuvers
5 of 47 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
8
8.8 mi into trip|~14m in
Keep slight left at fork toward I 90 East: Albany
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / slight right lanes.
Exit 1-49
Toward I 90 East: Albany
8
108.9 mi into trip|~2h 10m in
Take the exit toward NY 414: Waterloo, Clyde
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 41
Toward NY 414: Waterloo, Clyde
9
259.1 mi into trip|~5h 26m in|US 6
Keep slight right at fork onto US 6 toward I 84 East, I 380 South, US 6 East: Carbondale, Mt Pocono
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left / slight right lanes.
Exit 187
Toward I 84 East, I 380 South, US 6 East: Carbo...
8
373.7 mi into trip|~7h 42m in
Keep slight left at fork toward I 95 North: George Washington Bridge, New York City
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 95 North: George Washington Bridge, Ne...
9
374 mi into trip|~7h 43m in
Keep slight right at fork toward Leonia, Teaneck
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 70A-B
Toward Leonia, Teaneck
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Tonawanda, NY and Southold, NY, road signs point toward Clyde, Mt Pocono, Milford, New York City, Leonia and Teaneck - among others.
Clyde
108.9 mi in|~2h 10m
Mt Pocono
259.1 mi in|~5h 26m|via US 6
Milford
259.9 mi in|~5h 28m|via I 84; I 380
New York City
373.7 mi in|~7h 42m
Leonia
374 mi in|~7h 43m
Teaneck
374 mi in|~7h 43m
George Washington Bridge Upper Level
376.2 mi in|~7h 47m
Eastern Long Island
391.2 mi in|~8h 7m
Main Roads
Road
Distance
Duration
New York State Thruway
99.4 mi
1h 54m
I 81
98.8 mi
1h 57m
Keystone Shortway
80 mi
1h 37m
Long Island Expressway
58.9 mi
1h 20m
I 380
23.6 mi
25m
East Lake Road
9.9 mi
14m
State Highway 41
9.8 mi
13m
Clark Street Road
9.6 mi
11m
Longest stretch:
New York State Thruway
— 99.4 mi, about 1h 54m
Turn-by-Turn Driving Directions
Step-by-step road directions between Tonawanda, NY and Southold, NY.
1
Start on NY 265
0.1 mi·28 sec·Seymour Street
2
Turn left onto Broad Street
0.3 mi·42 sec·Broad Street
3
Continue on Young Street
0.8 mi·2 min·Young Street
4
Turn left
0.1 mi·28 sec
5
Turn straight onto NY 425
0.9 mi·1 min·Twin Cities Memorial Highway
6
Take the ramp
0.2 mi·30 sec
Toward I 290 East
7
Merge onto I 290
6.3 mi·8 min·Youngmann Expressway
8
Keep slight left at fork
0.6 mi·57 sec
Exit 1-49Toward I 90 East: AlbanyUse the slight left / slight right lanes.
9
Merge onto I 90
99 mi·1 hr 54 min·New York State Thruway
10
Take the exit
0.5 mi·58 sec
Exit 41Toward NY 414: Waterloo, ClydeUse the slight right lane.
11
Keep slight right at fork
327 ft·7 sec
12
Continue on NY 414
0.3 mi·35 sec·State Route 414
13
Turn left onto NY 318
4.1 mi·7 min·NY 318
Use the left lane.
14
At end of road, turn left onto US 20; NY 5
1.9 mi·2 min·Auburn Road
15
Continue on US 20; NY 5
9.6 mi·11 min·Clark Street Road
Use the straight lane.
16
Turn right onto State Street
226 ft·12 sec·State Street
17
Turn left onto Dill Street
0.1 mi·21 sec·Dill Street
18
Continue on Loop Road
458 ft·16 sec·Loop Road
19
Turn left onto Genesee Street
5.5 mi·9 min·Genesee Street
20
Continue on US 20
2.2 mi·4 min·West Genesee Street Road
21
Turn right onto NY 41
0.5 mi·45 sec·East Lake Street
22
Continue on NY 41
9.4 mi·13 min·East Lake Road
23
Continue on NY 41
4.8 mi·7 min·State Route 41
24
Continue on NY 41
0.5 mi·49 sec·East Lake Road
25
Continue on NY 41
9.8 mi·13 min·State Highway 41
26
Turn right onto NY 281
1.2 mi·2 min·North West Street
27
Take the ramp
0.7 mi·1 min
Use the left lane.
28
Keep slight right at fork
0.3 mi·34 sec
Toward I 81 South: Binghamton
29
Merge onto I 81
45 mi·54 min·I 81
Use the straight / slight right lanes.
30
Keep slight right at fork onto I 81
53 mi·1 hr 3 min·I 81
Toward I 81 South: ScrantonUse the straight lane.
31
Keep slight right at fork onto US 6
0.8 mi·1 min·US 6
Exit 187Toward I 84 East, I 380 South, US 6 East: Carbondale, Mt PoconoUse the slight left / slight right lanes.
32
Continue on I 84; I 380
3.7 mi·4 min·I 84; I 380
Toward I 84 East, I 380 South: Mount Pocono, MilfordUse the straight lane.
33
Keep slight right at fork onto I 380
24 mi·25 min·I 380
Exit 4Toward I 380 South: Mount Pocono
34
Keep slight left at fork
1.0 mi·1 min
Exit 1BToward I 80 East: Stroudsburg
35
Merge onto I 80
80 mi·1 hr 37 min·Keystone Shortway
Use the straight / right lanes.
36
Keep slight right at fork onto I 80
5.5 mi·5 min·Christopher Columbus Highway
Toward I 95: George Washington Bridge Lower LevelUse the slight right lane.
37
Keep slight left at fork
0.3 mi·23 sec
Toward I 95 North: George Washington Bridge, New York CityUse the straight / slight right lanes.
38
Keep slight right at fork
0.4 mi·38 sec
Exit 70A-BToward Leonia, TeaneckUse the slight right lane.
39
Turn right
0.2 mi·35 sec
Exit 70AToward LeoniaUse the straight / slight right lanes.
40
Turn straight onto CR 56
454 ft·9 sec·Degraw Avenue
41
Continue on CR 56
1.1 mi·2 min·Fort Lee Road
Use the straight / right lanes.
42
Continue on CR 56
469 ft·13 sec·Main Street
43
Take the ramp
472 ft·12 sec
Toward George Washington Bridge
44
Merge onto US 1; US 9; US 46
0.3 mi·28 sec·Bergen Boulevard
Use the straight / slight right lanes.
45
Take the exit
312 ft·4 sec
Toward George Washington Bridge Upper Level
46
Merge onto I 95 EXPR
0.3 mi·20 sec·I 95 EXPR
Use the straight / slight right lanes.
47
Keep slight left at fork onto I 95 EXPR
0.8 mi·1 min·I 95 EXPR
48
Continue on I 95; US 1; US 9
0.6 mi·1 min·George Washington Bridge (upper level)
Use the straight / slight right lanes.
49
Continue on I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
50
Continue on I 95; US 1
4.7 mi·6 min·Cross Bronx Expressway
Use the straight / slight right lanes.
51
Keep slight right at fork onto I 295
2.0 mi·2 min·Cross Bronx Expressway
Exit 6BToward I 295 South: Throgs Neck BridgeUse the straight / slight left lanes.
52
Merge onto I 295
0.6 mi·58 sec·Throgs Neck Expressway
53
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
Use the straight / slight right lanes.
54
Continue on I 295
3.2 mi·3 min·Clearview Expressway
Use the straight / slight right lanes.
55
Take the exit
0.2 mi·27 sec
Exit 4E-WToward I 495: Manhattan, Eastern Long IslandUse the straight / slight right lanes.
56
Keep slight left at fork
0.3 mi·38 sec
Exit 4EToward I 495 East: Long Island Expressway, Eastern Long Island
57
Merge onto I 495
59 mi·1 hr 20 min·Long Island Expressway
Use the straight / slight right lanes.
58
Keep slight left at fork
0.7 mi·1 min
Exit 73Toward CR 58 East: Old Country Road, Greenport, Orient
59
Keep slight left at fork
492 ft·14 sec
Toward CR 58 east: Greenport, Orient
60
Turn straight onto CR 58
2.3 mi·5 min·Old Country Road
Use the left lane.
61
Enter roundabout onto CR 58
108 ft·6 sec·Old Country Road
Toward Aquebogue, Greenport, Orient
62
Continue on CR 58
0.8 mi·1 min·Old Country Road
Toward Aquebogue, Greenport, Orient
63
Turn left onto CR 43
2.3 mi·3 min·Northville Turnpike
Use the left lane.
64
Turn right onto Sound Avenue
5.4 mi·8 min·Sound Avenue
65
Continue on CR 48; Truck NY 25
8.8 mi·12 min·Middle Road
Use the left lane.
66
Take the exit
232 ft·12 sec
Toward SoutholdUse the right lane.
67
Turn slight right onto Youngs Avenue
0.5 mi·1 min·Youngs Avenue
Use the right lane.
68
Arrive at destination
Youngs Avenue
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 235.7 miles from Tonawanda, NY, or about 4h 59m into the drive.
The longest continuous stretch on this route runs about 99.4 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 104 miles or 2h 4m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 235.7 miles or 4h 59m 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 235.7 miles or 4h 59m
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 8h 36m
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 Tonawanda, 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 Tonawanda, NY
Aim for roughly 236 miles and 5 hours of wheel time on this day.
Day 2
Finish the approach into Southold, NY
Aim for roughly 236 miles and 5 hours of wheel time on this day.
Your first comfortable stop window is around 104 miles from Tonawanda, 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 New York State Thruway for about 99.4 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 235.7 mi from Tonawanda, NY
· 4h 59m into the drive
The midpoint is around 235.7 miles from Tonawanda, NY, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel check
Top up before New York State Thruway if your tank is already low. That segment runs about 99.4 miles.
Overnight split
Hotel stop
For a steadier pace, wrap day one after about 236 miles or 5 hours on the road.
Arriving in Southold, NY
The final approach into Southold, NY usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Southold, NY.
On a multi-day trip, keep the last day a little lighter so you reach Southold, NY with some flexibility left in the schedule.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
National Parks Near This Route
Worth a detour if your schedule allows.
General Grant National Memorial
National Memorial
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...
4 mi from route
~11 min detour
Free
near mile 373.9
Caution: Lower Crypt Access Subject to Safe Conditions
Women’s Rights National Historical Park tells the story of the first Women’s Rights Convention, held in Seneca Falls, New York on July 19-20, 1848. It is a story of struggles for civil rights, human r...
4 mi from route
~10 min detour
Free
near mile 113.8
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...
5 mi from route
~11 min detour
Free
near mile 373.9
Harriet Tubman was guided by a deep faith and devotion to family, freedom, and community. After emancipating herself and members of her family, she moved them from Ontario, Canada to Fleming and Aubur...
5 mi from route
~12 min detour
Free
near mile 130.1
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
~23 min detour
Free
near mile 373.9
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
~26 min detour
Free
near mile 373.9
Park data from the National Park Service API. Alerts update every 2 hours.
Fuel & Cost
Regular Gas
$77.61 one way
$155.22 round trip
$4.18/gal25.4 MPG avg165 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$83.92
$167.85
premium
$4.92
$91.39
$182.77
diesel
$5.61
$104.10
$208.20
Estimated Tolls: $27.68
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
New York State Thruway
(99.4 mi)$4.97
Northville Turnpike
(2.3 mi)$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
$78
Tolls
$28
Hotel (1n)
$80–$140
Meals
$50–$100
Total
$235–$345
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 165 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $50 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
141.5
1
$49.51
$22.63
Efficient EV
117.9
1
$41.26
$18.86
EV Truck/SUV
188.6
2
$66.01
$30.18
Gas CO2
165 kg
EV CO2
55 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 15, 2026
Origin
Tonawanda, NY
Late night
in Tonawanda on Friday
Local time
12:21 AM
EDT
Current temp
44°F
Unavailable
Live forecast
Destination
Southold, NY
Late night
in Southold on Friday
Local time
12:21 AM
EDT
Current temp
59°F
Unavailable
Live forecast
57°F
Ramapo, NY
236 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
15 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
10h 4m 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 Tonawanda, NY to Southold, NY covers 471.5 miles and takes about 10h 4m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are New York State Thruway, I 81, Keystone Shortway. 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 236 miles on day one.
The midpoint is about 235.7 miles from Tonawanda, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $77.61 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 47 significant decision points across 471.5 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 8.8 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 108.9 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 259.1 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Between Tonawanda, NY and Southold, NY, road signs point toward Clyde, Mt Pocono, Milford, New York City, Leonia and Teaneck - among others.
Yes. Nearby national parks include General Grant National Memorial, Women's Rights National Historical Park and Hamilton Grange National Memorial. There are 6 parks within detour distance of this route.
