The drive from Callicoon, NY to Oyster Bay, NY covers 134.8 miles and takes about 3h 3m behind the wheel.
This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on NY 17, State Highway 17B, Northern Boulevard for much of the mileage,
and the overall profile is highway-focused drive.
The longest uninterrupted segment is about 44.7 miles on NY 17.
At current regular gas prices, budget about $22.19 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.
Break Rhythm
1 planned break
A short stop every 2 to 3 hours is enough for this drive.
Midpoint
67.4 miles from Callicoon, NY
A natural place for your longest stop of the day
, about 1h 27m 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 3h 3m. Total distance: 134.8 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
3h 3m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (74%). Some complex stretches to watch for.
Drive Character
This is a 3h 3m highway drive covering 134.8 miles, with most of the trip on NY 17 and State Highway 17B. The longest continuous stretch is about 44.7 miles on NY 17.
Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 39 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
NY 17 is the longest continuous segment at about 44.7 miles.
How Hard Is This Drive?
This is a straightforward highway drive that stays mostly on NY 17 and State Highway 17B. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 65.9 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 22 significant decision points across 134.8 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 65.9 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 66.6 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 81.2 miles (NY 17): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Critical Maneuvers
5 of 22 key points
These are the spots where you need to pay the most attention. Preview them before you drive.
8
65.9 mi into trip|~1h 25m in
Keep slight left at fork toward I 87, NYST: Albany, New York City
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Toward I 87, NYST: Albany, New York City
7
66.6 mi into trip|~1h 26m in
Keep slight right at fork toward I 87 Toll South: New York City
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Toward I 87 Toll South: New York City
9
81.2 mi into trip|~1h 43m in|NY 17
Keep slight right at fork onto NY 17 toward I 287 South, NJ 17 South: New Jersey
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Exit 15
Toward I 287 South, NJ 17 South: New Jersey
8
82.5 mi into trip|~1h 45m in|NJ 17
Keep slight left at fork onto NJ 17 toward NJ 17 South: Mahwah
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight left / straight lanes.
Exit 66
Toward NJ 17 South: Mahwah
8
111.6 mi into trip|~2h 25m 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 Callicoon, NY and Oyster Bay, NY, road signs point toward Nyst: Albany, New York City, Gsp South: Paterson, Fort Lee and New York.
Nyst: Albany
65.9 mi in|~1h 25m
New York City
65.9 mi in|~1h 25m
Gsp South: Paterson
96.6 mi in|~2h 4m
Fort Lee
96.6 mi in|~2h 4m
New York
96.6 mi in|~2h 4m
Main Roads
Road
Distance
Duration
NY 17
44.7 mi
53m
State Highway 17B
21.7 mi
31m
Northern Boulevard
14.5 mi
24m
NJ 17
14.1 mi
18m
New York State Thruway
13.7 mi
15m
NJ 4
6.7 mi
9m
Cross Bronx Expressway
6.6 mi
8m
Clearview Expressway
2.1 mi
2m
Longest stretch:
NY 17
— 44.7 mi, about 53m
Turn-by-Turn Driving Directions
Step-by-step road directions between Callicoon, NY and Oyster Bay, NY.
1
Start on Hospital Road
22 ft·6 sec·Hospital Road
2
Turn left onto NY 97
0.2 mi·17 sec·State Highway 97
3
Turn left onto NY 17B
425 ft·7 sec·Mill Street
4
Turn slight left onto NY 17B
5.1 mi·7 min·State Highway 17B
5
Continue on NY 17B; CR 117
1.7 mi·2 min·State Highway 17B
6
Continue on NY 17B
15 mi·21 min·State Highway 17B
7
Take the ramp
0.2 mi·27 sec
Toward NY 17 East: New York
8
Merge onto NY 17
44 mi·52 min·NY 17
Use the straight / slight right lanes.
9
Keep slight left at fork
0.7 mi·59 sec
Toward I 87, NYST: Albany, New York CityUse the slight right lane.
10
Keep slight right at fork
0.9 mi·1 min
Toward I 87 Toll South: New York CityUse the slight right lane.
11
Merge onto I 87
14 mi·15 min·New York State Thruway
Use the straight / slight right lanes.
12
Keep slight right at fork onto NY 17
0.9 mi·59 sec·NY 17
Exit 15Toward I 287 South, NJ 17 South: New JerseyUse the slight right lane.
13
Continue on I 287; NJ 17
0.5 mi·39 sec·I 287; NJ 17
14
Keep slight left at fork onto NJ 17
14 mi·18 min·NJ 17
Exit 66Toward NJ 17 South: MahwahUse the slight left / straight lanes.
15
Take the exit
0.1 mi·19 sec
Toward NJ 4, GSP South: Paterson, Fort Lee, New York
16
Keep slight left at fork
0.5 mi·1 min
Toward NJ 4 East: Fort Lee, New York
17
Merge onto NJ 4
0.3 mi·24 sec·NJ 4
Use the right lane.
18
Continue on NJ 4
6.4 mi·8 min·NJ 4
Use the straight / slight right lanes.
19
Take the exit
0.2 mi·18 sec
Toward I 95 North: George Washington BridgeUse the straight / slight left lanes.
20
Merge onto I 95 EXPR
0.7 mi·54 sec·I 95 EXPR
Use the straight / slight right lanes.
21
Keep slight left at fork onto I 95 EXPR
0.8 mi·1 min·I 95 EXPR
22
Continue on I 95; US 1; US 9
0.6 mi·1 min·George Washington Bridge (upper level)
Use the straight / slight right lanes.
23
Continue on I 95; US 1
0.7 mi·1 min·Trans-Manhattan Expressway
24
Continue on I 95; US 1
4.7 mi·6 min·Cross Bronx Expressway
Use the straight / slight right lanes.
25
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.
26
Merge onto I 295
0.6 mi·58 sec·Throgs Neck Expressway
27
Continue on I 295
2.0 mi·3 min·Throgs Neck Bridge
Use the straight / slight right lanes.
28
Continue on I 295
2.0 mi·2 min·Clearview Expressway
Use the straight / slight right lanes.
29
Take the exit
0.2 mi·32 sec
Exit 5Toward NY 25A: Northern BoulevardUse the straight / slight right lanes.
30
Continue on Clearview Expressway
457 ft·17 sec·Clearview Expressway
31
Turn left onto NY 25A
15 mi·24 min·Northern Boulevard
Use the left lane.
32
Turn left onto NY 106
0.3 mi·29 sec·Jericho Oyster Bay Road
33
Turn straight onto NY 106
0.5 mi·46 sec·Oyster Bay Road
34
Keep slight left at fork onto NY 106
260 ft·4 sec·Oyster Bay Road
35
Continue on NY 106
0.9 mi·1 min·Pine Hollow Road
Use the left lane.
36
Continue on NY 106
105 ft·5 sec·South Street
37
Turn right onto Berry Hill Road
112 ft·9 sec·Berry Hill Road
38
Continue on Berry Hill Road
64 ft·2 sec·Berry Hill Road
39
Arrive at destination
Berry Hill Road
Trip Plan
Morning Departure
An early start around 7-8 AM gets you there with plenty of daylight left.
Evening Departure
A late afternoon start means arriving after dark. Morning is better.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 67.4 miles from Callicoon, NY, or about 1h 27m into the drive.
The longest continuous stretch on this route runs about 44.7 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 30 miles or 41m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 67.4 miles or 1h 27m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 2h 24m
Traffic, exits, and arrival timing usually matter more near Oyster Bay, NY than in the middle of the route.
Before You Leave
+
Open the route before leaving Callicoon, 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 Callicoon, NY
This is one driving day of about 134.8 miles and 3h 3m.
Your first comfortable stop window is around 30 miles from Callicoon, 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 NY 17 for about 44.7 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 67.4 mi from Callicoon, NY
· 1h 27m 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.
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...
2 mi from route
~5 min detour
Free
near mile 106.9
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...
3 mi from route
~7 min detour
Free
near mile 106.9
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
~21 min detour
Free
near mile 106.9
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
~25 min detour
Free
near mile 106.9
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...
10 mi from route
~26 min detour
Free
near mile 106.9
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...
11 mi from route
~27 min detour
Free
near mile 106.9
Station data from NREL Alternative Fuel Stations database.
Driving Electric?
About $14 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
40.4
0
$14.15
$6.47
Efficient EV
33.7
0
$11.80
$5.39
EV Truck/SUV
53.9
0
$18.87
$8.63
Gas CO2
47 kg
EV CO2
16 kg (66% 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 17, 2026
Origin
Callicoon, NY
Late night
in Callicoon on Saturday
Local time
12:18 AM
EDT
Current temp
39°F
Unavailable
Live forecast
Destination
Oyster Bay, NY
Late night
in Oyster Bay on Saturday
Local time
12:18 AM
EDT
Current temp
51°F
Scattered Rain Showers then Partly Cloudy
E 5 to 8 mph32% chanceLive forecast
57°F
Ramapo, NY
67 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
12 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
3h 3m on the road
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
Frequently Asked Questions
The drive from Callicoon, NY to Oyster Bay, NY covers 134.8 miles and takes about 3h 3m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are NY 17, State Highway 17B, Northern Boulevard. Most of the drive stays on highways, so watch for ramps and exits.
This is a comfortable same-day trip.
The midpoint is about 67.4 miles from Callicoon, NY. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $22.19 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
An early start around 7-8 AM gets you there with plenty of daylight left. A late afternoon start means arriving after dark. Morning is better.
Plan about 1 meaningful break for fuel, food, or rest. A short stop every 2 to 3 hours is enough for this drive.
This is a demanding drive. With 22 significant decision points across 134.8 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 65.9 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 66.6 miles: Highway fork - watch signs carefully. Lane positioning matters here; at 81.2 miles (NY 17): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Between Callicoon, NY and Oyster Bay, NY, road signs point toward Nyst: Albany, New York City, Gsp South: Paterson, Fort Lee and New York.
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, NREL for EV charging, and NPS for national parks. See our methodology for refresh cadence and limitations.
