This 377.4-mile journey from Oyster Bay, NY to Bennington, NY will take approximately 7 hours and 54 minutes of driving time. It's a solid day trip option, covering a significant distance within New York State. The route is primarily highway-focused, utilizing major interstates like I-86 and I-81, along with Christopher Columbus Highway. With an estimated fuel cost of $62, it's a budget-friendly option for a single day's adventure. You'll spend most of your time on well-maintained highways, making for a generally straightforward drive.
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
188.7 miles from Oyster Bay, NY
A natural place for your longest stop of the day
, about 3h 58m into the drive
.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 7h 54m. Total distance: 377.4 miles.
Family Friendly
Moderate complexity with 2 natural rest stops along the way.
Solo Traveler
7h 54m drive, plan rest stops for pacing.
Drive Character
Expect a highway-focused drive for about 62% of this trip. You'll be spending a good portion of your time on interstates, including a significant 100-mile stretch on I-86. This means consistent speeds and relatively few traffic lights for extended periods. While the majority is highway, be prepared for the character to shift as you transition between major routes. The uninterrupted highway segments offer a chance to make good time, so plan your stops accordingly.
Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 42 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
I 86 is the longest continuous segment at about 100 miles.
How Hard Is This Drive?
This is a straightforward highway drive that stays mostly on I 86 and Christopher Columbus Highway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 15.1 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 26 significant decision points across 377.4 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 15.1 miles: Lane positioning matters here. Multiple destination signs - pick the right one; at 17.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 29.8 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Critical Maneuvers
5 of 26 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
7
15.1 mi into trip|~25m in
Take the ramp toward Cross Island Parkway North, Whitestone Bridge
Lane positioning matters here. Multiple destination signs - pick the right one
Use the right lane.
Toward Cross Island Parkway North, Whitestone B...
8
17.6 mi into trip|~29m in
Take the exit toward I 295 North: Throgs Neck Bridge, Bronx, New England
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 33
Toward I 295 North: Throgs Neck Bridge, Bronx,...
8
29.8 mi into trip|~47m in
Take the exit toward I 95 South, NJTP South: Hackensack
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 95 South, NJTP South: Hackensack
8
30.1 mi into trip|~48m in
Keep slight left at fork toward I 95 South, NJTP South: Hackensack
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left / slight right lanes.
Toward I 95 South, NJTP South: Hackensack
8
32.4 mi into trip|~51m in
Take the exit toward I 80 West: Paterson, Hackensack
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 69
Toward I 80 West: Paterson, Hackensack
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Oyster Bay, NY and Bennington, NY, road signs point toward Upper Level, Njtp South: Hackensack, Hackensack and Letchworth Park.
Upper Level
27.3 mi in|~43m|via I 95; US 1
Njtp South: Hackensack
29.8 mi in|~47m
Hackensack
32.4 mi in|~51m
Letchworth Park
338.1 mi in|~6h 52m
Main Roads
Road
Distance
Duration
I 86
100 mi
1h 56m
Christopher Columbus Highway
68.2 mi
1h 20m
I 81
58.1 mi
1h 9m
Genesee Expressway
32.9 mi
37m
I 380
27.7 mi
30m
Keystone Shortway
17.3 mi
24m
Northern Boulevard
13.4 mi
22m
Varysburg Road
10.9 mi
15m
Longest stretch:
I 86
— 100 mi, about 1h 56m
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay, NY and Bennington, NY.
1
Start on Berry Hill Road
288 ft·21 sec·Berry Hill Road
2
Turn sharp left onto NY 106
429 ft·9 sec·South Street
3
Continue on NY 106
0.9 mi·1 min·Pine Hollow Road
4
Continue on NY 106
0.7 mi·1 min·Oyster Bay Road
5
Turn right onto NY 25A
13 mi·22 min·Northern Boulevard
Use the left lane.
6
Take the ramp
0.2 mi·28 sec
Toward Cross Island Parkway North, Whitestone BridgeUse the right lane.
7
Merge onto CI
2.3 mi·3 min·Cross Island Parkway
Use the straight / slight right lanes.
8
Take the exit
0.6 mi·1 min
Exit 33Toward I 295 North: Throgs Neck Bridge, Bronx, New EnglandUse the straight / slight right lanes.
9
Merge onto I 295
1.8 mi·3 min·Throgs Neck Bridge
10
Continue on I 295
0.7 mi·1 min·Throgs Neck Expressway
Use the straight / slight right lanes.
11
Keep slight left at fork onto I 295
6.6 mi·8 min·Cross Bronx Expressway
Use the straight / slight right lanes.
12
Keep slight left at fork onto I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
Toward Upper Level
13
Continue on I 95; US 1
0.6 mi·59 sec·George Washington Bridge (upper level)
14
Continue on I 95 EXPR; US 1 EXPR; US 9 EXPR
0.5 mi·48 sec·I 95 EXPR; US 1 EXPR; US 9 EXPR
15
Keep slight left at fork onto I 95 EXPR; US 1 EXPR; US 9 EXPR
0.6 mi·39 sec·I 95 EXPR; US 1 EXPR; US 9 EXPR
Use the straight / slight right lanes.
16
Keep slight left at fork onto I 95 EXPR; NJTP
0.1 mi·8 sec·I 95 EXPR; NJTP
17
Take the exit
0.2 mi·22 sec
Toward I 95 South, NJTP South: HackensackUse the straight / slight right lanes.
18
Keep slight left at fork
0.4 mi·29 sec
Toward I 95 South, NJTP South: HackensackUse the slight left / slight right lanes.
19
Merge onto I 95; NJTP
2.0 mi·2 min·New Jersey Turnpike
Use the straight / slight right lanes.
20
Take the exit
0.8 mi·1 min
Exit 69Toward I 80 West: Paterson, HackensackUse the straight / slight right lanes.
21
Continue on I 80
68 mi·1 hr 20 min·Christopher Columbus Highway
Use the straight / slight right lanes.
22
Keep slight left at fork onto I 80
5.5 mi·8 min·Keystone Shortway
Use the straight / slight right lanes.
23
Keep slight left at fork onto I 80
12 mi·15 min·Keystone Shortway
24
Take the exit
0.7 mi·46 sec
Exit 293Toward I 380 North: Scranton
25
Continue on I 380
28 mi·30 min·I 380
Use the straight lane.
26
Merge onto I 81
58 mi·1 hr 9 min·I 81
Use the straight lane.
27
Keep slight left at fork onto I 86; NY 17
100 mi·1 hr 56 min·I 86; NY 17
Toward I 86: Corning
28
Keep slight left at fork onto I 390
33 mi·37 min·Genesee Expressway
Toward I 390: Rochester
29
Take the exit
0.2 mi·23 sec
Exit 6Toward NY 36: Mount Morris, Letchworth Park
30
Turn left onto NY 36
4.3 mi·7 min·Sonyea Road
31
Continue on NY 36
1.8 mi·4 min·Main Street
32
Continue on NY 36
1.3 mi·1 min·Mount Morris Road
33
Turn left onto CR 64
2.3 mi·3 min·Perry Road
34
Continue on US 20A
7.4 mi·10 min·Leicester Road
35
Continue on US 20A
4.6 mi·8 min·East Buffalo Street
36
Continue on US 20A
1.7 mi·2 min·West Buffalo Road
37
Continue on US 20A
11 mi·15 min·Varysburg Road
38
Turn right onto NY 77
0.8 mi·1 min·State Highway 77
39
Continue on NY 77
4.0 mi·5 min·Alleghany Road
40
Turn right
0.1 mi·24 sec
41
Turn left onto NY 354
75 ft·1 sec·Clinton Street
42
Arrive at destination
NY 354
Trip Plan
To maximize your daylight, aim for an early morning departure from Oyster Bay. With 7 hours and 54 minutes of estimated driving, planning for two stops will help break up the journey comfortably. Keep an eye on your fuel gauge, especially during the 100-mile stretch on I-86, as services can be more spread out. Since this route is manageable in a single day, you have the flexibility to adjust your stop times based on how you feel. Consider using a navigation app that highlights upcoming rest areas or fuel stations to avoid any last-minute searches.
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.
You can normally do this drive in one day.
Plan roughly 2 meaningful breaks for fuel, food, and rest.
The halfway point lands around 188.7 miles from Oyster Bay, NY, or about 3h 58m into the drive.
The longest continuous stretch on this route runs about 100 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 83 miles or 1h 51m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 188.7 miles or 3h 58m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 6h 28m
Traffic, exits, and arrival timing usually matter more near Bennington, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Oyster 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.
+
Pick one backup stop option before the midpoint in case traffic changes your pacing.
Day 1
Settle into the route from Oyster Bay, NY
This is one driving day of about 377.4 miles and 7h 54m.
Your first comfortable stop window is around 83 miles from Oyster Bay, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 2 real breaks rather than only quick fuel stops.
The longest stretch is on I 86 for about 100 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 188.7 mi from Oyster Bay, NY
· 3h 58m into the drive
The midpoint is around 188.7 miles from Oyster Bay, NY, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel check
Top up before I 86 if your tank is already low. That segment runs about 100 miles.
Arriving in Bennington, NY
The final approach into Bennington, 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 Bennington, NY.
After long uninterrupted mileage, take five minutes before the last urban segment to reset and refocus on exits, merges, and city traffic.
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.
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...
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...
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...
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...
Park data from the National Park Service API. Alerts update every 2 hours.
Fuel & Cost
Regular Gas
$62.12 one way
$124.24 round trip
$4.18/gal25.4 MPG avg132 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$67.17
$134.35
premium
$4.92
$73.15
$146.29
diesel
$5.61
$83.33
$166.65
Estimated Tolls: $22.83
George Washington Bridge
$16.00
Throgs Neck Bridge
$6.55
New Jersey Turnpike
(2 mi)$0.28
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
$39.63
$18.12
Efficient EV
94.4
1
$33.02
$15.10
EV Truck/SUV
151
1
$52.84
$24.15
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 16, 2026
Origin
Oyster Bay, NY
Late night
in Oyster Bay on Friday
Local time
2:54 AM
EDT
Current temp
45°F
Unavailable
Live forecast
Destination
Bennington, NY
Late night
in Bennington on Friday
Local time
2:54 AM
EDT
Current temp
43°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 cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
7h 54m 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 Oyster Bay, NY to Bennington, NY covers 377.4 miles and takes about 7h 54m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are I 86, Christopher Columbus Highway, 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 188.7 miles from Oyster Bay, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $62.12 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 26 significant decision points across 377.4 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 15.1 miles: Lane positioning matters here. Multiple destination signs - pick the right one; at 17.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 29.8 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Between Oyster Bay, NY and Bennington, NY, road signs point toward Upper Level, Njtp South: Hackensack, Hackensack and Letchworth Park.
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.
