The drive from Oyster Bay, NY to Dundee, NY covers 295.7 miles and takes about 6h 15m behind the wheel.
This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Christopher Columbus Highway, I 86, I 81 for much of the mileage,
and the overall profile is mixed drive.
The longest uninterrupted segment is about 68.2 miles on Christopher Columbus Highway.
At current regular gas prices, budget about $48.67 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
1 planned break
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
147.8 miles from Oyster Bay, NY
A natural place for your longest stop of the day
, about 3h 9m 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 6h 15m. Total distance: 295.7 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
6h 15m drive, plan rest stops for pacing.
Scenic Drive
Mixed drive route profile with national parks nearby.
Drive Character
The drive from Oyster Bay, NY to Dundee, NY covers 295.7 miles and takes about 6h 15m, using a mix of highways and local roads.
Expect a mix of faster highway mileage and slower local approaches near the beginning or end.
There are about 42 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Christopher Columbus Highway is the longest continuous segment at about 68.2 miles.
How Hard Is This Drive?
This route mixes highway mileage with some local-road sections near the start or finish. 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 27 significant decision points across 295.7 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 27 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 Dundee, NY, road signs point toward Cross Island Parkway North, Bronx, New England, Upper Level, Njtp South: Hackensack and Hackensack - among others.
Cross Island Parkway North
15.1 mi in|~25m
Bronx
17.6 mi in|~29m
New England
17.6 mi in|~29m
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
Cr 64: Watkins Glen
266.1 mi in|~5h 29m
Main Roads
Road
Distance
Duration
Christopher Columbus Highway
68.2 mi
1h 20m
I 86
60.9 mi
1h 11m
I 81
58.1 mi
1h 9m
I 380
27.7 mi
30m
Keystone Shortway
17.3 mi
24m
Northern Boulevard
13.4 mi
22m
Watkins Road
11.6 mi
15m
North Madison Avenue
8.7 mi
11m
Longest stretch:
Christopher Columbus Highway
— 68.2 mi, about 1h 20m
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay, NY and Dundee, 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
61 mi·1 hr 11 min·I 86; NY 17
Toward I 86: Corning
28
Take the exit
0.2 mi·37 sec
Exit 52AToward NY 14 North, CR 64: Watkins Glen
29
Turn left onto CR 64
0.1 mi·9 sec·County Road 64
30
Take the exit
0.1 mi·22 sec
31
Merge onto NY 14
1.4 mi·1 min·Westinghouse Road
32
At end of road, turn left onto NY 14
5.6 mi·7 min·Watkins Road
33
Continue on NY 14
1.5 mi·3 min·Main Street
34
Continue on NY 14
6.0 mi·7 min·Watkins Road
35
Continue on NY 14
2.3 mi·4 min·South Franklin Street
Use the straight lane.
36
Continue on NY 14
385 ft·5 sec·Lake Shore Drive
37
Continue on NY 14
8.7 mi·11 min·North Madison Avenue
38
Turn left onto Dundee-Glenora Road
3.0 mi·7 min·Dundee-Glenora Road
39
Continue on Saunders Street
0.3 mi·37 sec·Saunders Street
40
Turn right onto NY 14A
0.4 mi·40 sec·Main Street
41
Turn right onto Seneca Street
75 ft·2 sec·Seneca Street
42
Arrive at destination
Seneca Street
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.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 147.8 miles from Oyster Bay, NY, or about 3h 9m into the drive.
The longest continuous stretch on this route runs about 68.2 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 65 miles or 1h 30m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 147.8 miles or 3h 9m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 5h 1m
Traffic, exits, and arrival timing usually matter more near Dundee, 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.
Day 1
Settle into the route from Oyster Bay, NY
This is one driving day of about 295.7 miles and 6h 15m.
Your first comfortable stop window is around 65 miles from Oyster Bay, NY.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 1 real break rather than only quick fuel stops.
The longest stretch is on Christopher Columbus Highway for about 68.2 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 147.8 mi from Oyster Bay, NY
· 3h 9m 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.
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
~10 min detour
Free
near mile 30.6
Caution: Lower Crypt Access Subject to Safe Conditions
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...
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 30.6
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 30.6
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 30.6
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 30.6
Park data from the National Park Service API. Alerts update every 2 hours.
Fuel & Cost
Regular Gas
$48.67 one way
$97.35 round trip
$4.18/gal25.4 MPG avg104 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$52.63
$105.26
premium
$4.92
$57.31
$114.62
diesel
$5.61
$65.29
$130.57
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
$49
Tolls
$23
Meals
$25–$50
Total
$97–$122
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 103.5 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $31 in charging
· 1 stop
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
88.7
1
$31.05
$14.19
Efficient EV
73.9
0
$25.87
$11.83
EV Truck/SUV
118.3
1
$41.40
$18.92
Gas CO2
103 kg
EV CO2
35 kg (66% 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 18, 2026
Origin
Oyster Bay, NY
Morning
in Oyster Bay on Saturday
Local time
7:40 AM
EDT
Current temp
51°F
Scattered Rain Showers then Partly Cloudy
E 5 to 8 mph32% chanceLive forecast
Destination
Dundee, NY
Morning
in Dundee on Saturday
Local time
7:40 AM
EDT
Current temp
41°F
Unavailable
Live forecast
57°F
Ramapo, NY
148 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
10 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
6h 15m 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 Dundee, NY covers 295.7 miles and takes about 6h 15m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Christopher Columbus Highway, I 86, I 81. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 147.8 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 $48.67 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 1 meaningful break 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 27 significant decision points across 295.7 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 Dundee, NY, road signs point toward Cross Island Parkway North, Bronx, New England, Upper Level, Njtp South: Hackensack and Hackensack - among others.
Yes. Nearby national parks include General Grant National Memorial, Hamilton Grange 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.
