The drive from Bennington, NY to Oyster Bay, NY covers 377.2 miles and takes about 7h 53m behind the wheel.
This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Southern Tier Expressway, Keystone Shortway, I 81 for much of the mileage,
and the overall profile is highway-focused drive.
The longest uninterrupted segment is about 104.5 miles on Southern Tier Expressway.
At current regular gas prices, budget about $62.09 one way before food or hotel costs.
Trip Pace
Same-day drive is realistic
A same-day return is possible, but it will make for a full day on the road.
Break Rhythm
2 planned breaks
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
188.6 miles from Bennington, NY
A natural place for your longest stop of the day
, about 3h 56m into the drive
.
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 7h 53m. Total distance: 377.2 miles.
Family Friendly
Moderate complexity with 2 natural rest stops along the way.
Solo Traveler
7h 53m drive, plan rest stops for pacing.
Drive Character
This is a 7h 53m highway drive covering 377.2 miles, with most of the trip on Southern Tier Expressway and Keystone Shortway. The longest continuous stretch is about 104.5 miles on Southern Tier Expressway.
Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 51 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Southern Tier Expressway is the longest continuous segment at about 104.5 miles.
How Hard Is This Drive?
This is a straightforward highway drive that stays mostly on Southern Tier Expressway and Keystone Shortway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 176.4 miles in near I 81.
Driving Effort9/10
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 28 significant decision points across 377.2 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 176.4 miles (I 81): Highway fork - watch signs carefully. Lane positioning matters here; at 229.8 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 344.3 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Critical Maneuvers
5 of 28 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
7
176.4 mi into trip|~3h 41m in|I 81
Keep slight right at fork onto I 81 toward I 81 South: Scranton
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight lane.
Toward I 81 South: Scranton
9
229.8 mi into trip|~4h 45m 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
344.3 mi into trip|~7h 1m 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
344.6 mi into trip|~7h 1m 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
8
354 mi into trip|~7h 15m in|I 295 / Cross Bronx Expressway
Keep slight right at fork onto I 295 / Cross Bronx Expressway toward I 295 South: Throgs Neck Bridge
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight left lanes.
Exit 6B
Toward I 295 South: Throgs Neck Bridge
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Bennington, NY and Oyster Bay, NY, road signs point toward Mt Pocono, Milford, New York City, Leonia, Teaneck and George Washington Bridge Upper Level.
Place data sourced from public business listings. Hours and availability may vary.
National Parks Near This Route
Worth a detour if your schedule allows.
Hamilton Grange National Memorial
National Memorial
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...
3 mi from route
~8 min detour
Free
near mile 351.2
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
~10 min detour
Free
near mile 351.2
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
~24 min detour
Free
near mile 351.2
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...
11 mi from route
~27 min detour
Free
near mile 351.2
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...
11 mi from route
~28 min detour
Free
near mile 351.2
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...
12 mi from route
~29 min detour
Free
near mile 351.2
Park data from the National Park Service API. Alerts update every 2 hours.
Fuel & Cost
Regular Gas
$62.09 one way
$124.18 round trip
$4.18/gal25.4 MPG avg132 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$67.14
$134.28
premium
$4.92
$73.11
$146.22
diesel
$5.61
$83.28
$166.56
Estimated Tolls: $22.55
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
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
$62
Tolls
$23
Meals
$25–$50
Total
$110–$135
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 132 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $40 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
113.2
1
$39.61
$18.11
Efficient EV
94.3
1
$33.00
$15.09
EV Truck/SUV
150.9
1
$52.81
$24.14
Gas CO2
132 kg
EV CO2
44 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
Bennington, NY
Late night
in Bennington on Saturday
Local time
3:27 AM
EDT
Current temp
43°F
Unavailable
Live forecast
Destination
Oyster Bay, NY
Late night
in Oyster Bay on Saturday
Local time
3:27 AM
EDT
Current temp
45°F
Unavailable
Live forecast
57°F
Ramapo, NY
189 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
2 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
7h 53m on the road
Start early — leave by 6-7 AM to arrive at a reasonable hour.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
Frequently Asked Questions
The drive from Bennington, NY to Oyster Bay, NY covers 377.2 miles and takes about 7h 53m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Southern Tier Expressway, Keystone Shortway, I 81. Most of the drive stays on highways, so watch for ramps and exits.
This is a comfortable same-day trip.
The midpoint is about 188.6 miles from Bennington, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $62.09 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 28 significant decision points across 377.2 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 176.4 miles (I 81): Highway fork - watch signs carefully. Lane positioning matters here; at 229.8 miles (US 6): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 344.3 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Between Bennington, NY and Oyster Bay, NY, road signs point toward Mt Pocono, Milford, New York City, Leonia, Teaneck and George Washington Bridge Upper Level.
Yes. Nearby national parks include Hamilton Grange National Memorial, General Grant National Memorial and Stonewall 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.
