Oyster Bay to Rhinebeck is 106.6 miles and takes about 2h 38m via Albany Post Road and NY 9A, with a fuel budget near $18 and enough daylight to finish in a day. This one-day drive stays within New York, transitioning from the Northeast region to another part of the Northeast. Expect a route that involves frequent turns, making it more of a local exploration than a straightforward highway journey. Given its relatively short duration, it's an accessible trip for a single day, allowing ample time for any necessary stops or detours.
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
53.3 miles from Oyster Bay, NY
A natural place for your longest stop of the day
, about 1h 25m into the drive
.
Main Roads
Road
Distance
Duration
Albany Post Road
33.7 mi
44m
NY 9A
14.7 mi
22m
Northern Boulevard
13.4 mi
22m
Sprain Brook Parkway
12.6 mi
17m
South Road
11 mi
15m
Throgs Neck Expressway
2.5 mi
3m
South Columbus Avenue
2.3 mi
3m
Cross Island Parkway
2.3 mi
3m
Longest stretch:
Albany Post Road
— 33.7 mi, about 44m
Turn-by-Turn Driving Directions
Step-by-step road directions between Oyster Bay, NY and Rhinebeck, 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 right at fork onto I 695
1.8 mi·2 min·Throgs Neck Expressway
Exit 10Toward I 695 North: New HavenUse the straight / slight right lanes.
12
Merge onto I 95
1.0 mi·1 min·Bruckner Expressway
13
Continue on I 95
2.0 mi·3 min·New England Thruway
Use the straight / slight left lanes.
14
Take the exit
351 ft·16 sec
Exit 13Toward Conner StreetUse the slight right lane.
15
Turn left onto Tillotson Avenue
0.1 mi·22 sec·Tillotson Avenue
16
Turn left onto Conner Street
0.3 mi·30 sec·Conner Street
17
Continue on NY 22
0.3 mi·59 sec·Provost Avenue
18
Continue on NY 22
0.2 mi·17 sec·South 3rd Avenue
19
Turn slight right onto NY 22
2.3 mi·3 min·South Columbus Avenue
Use the left / straight lanes.
20
Take the ramp
0.3 mi·37 sec
Toward Cross County Parkway WestUse the left lane.
21
Merge onto Cross County Parkway
0.6 mi·54 sec·Cross County Parkway
22
Take the exit
0.1 mi·18 sec
Exit 6Toward Bronx Parkway, Sprain ParkwayUse the straight / slight right lanes.
23
Keep slight right at fork
0.4 mi·1 min
Toward Bronx Parkway North, Sprain ParkwayUse the slight left / slight right lanes.
24
Merge onto Bronx River Parkway
0.3 mi·32 sec·Bronx River Parkway
25
Keep slight left at fork onto Sprain Brook Parkway
13 mi·17 min·Sprain Brook Parkway
Use the straight / slight right lanes.
26
Continue on Taconic State Parkway
1.8 mi·2 min·Taconic State Parkway
Use the straight / slight right lanes.
27
Take the exit
0.5 mi·1 min
Exit 5Toward NY 9A, NY 100 NorthUse the slight right lane.
28
Continue on NY 9A; NY 100
15 mi·22 min·NY 9A; NY 100
29
Turn left onto US 6; US 9; US 202
0.2 mi·12 sec·US 6; US 9; US 202
30
Enter roundabout onto US 9
21 ft·0 sec·Albany Post Road
Toward Fishkill
31
Continue on US 9
23 mi·30 min·Albany Post Road
Toward FishkillUse the straight lane.
32
Continue on US 9
8.2 mi·11 min·South Road
Use the straight / slight right lanes.
33
Continue on US 9
1.2 mi·1 min·North Road
34
Continue on US 9
11 mi·13 min·Albany Post Road
35
Continue on US 9
2.7 mi·4 min·South Road
36
Continue on US 9
0.5 mi·1 min·Mill Street
37
Arrive at destination
US 9
Trip Plan
Since this is a single-day drive of under 3 hours, you have the flexibility to depart whenever suits you best, though an early start will maximize your daylight. Plan for at least one stop to break up the 106.6 miles and manage the frequent turns. Keep an eye on your fuel; with a projected cost of $18, it's wise to top up before you leave Oyster Bay or at your planned stop. A good tip for this route is to familiarize yourself with the Albany Post Road section, as it represents the longest continuous stretch and will likely be where you spend a good portion of your driving time.
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 53.3 miles from Oyster Bay, NY, or about 1h 25m into the drive.
The longest continuous stretch on this route runs about 33.7 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 23 miles or 38m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 53.3 miles or 1h 25m 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 12m
Traffic, exits, and arrival timing usually matter more near Rhinebeck, 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 106.6 miles and 2h 38m.
Your first comfortable stop window is around 23 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 Albany Post Road for about 33.7 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 22
5 decision points cluster between mile 17.6 and 44.9 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
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
20.7 mi into trip|~35m in|I 695 / Throgs Neck Expressway
Keep slight right at fork onto I 695 / Throgs Neck Expressway toward I 695 North: New Haven
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Exit 10
Toward I 695 North: New Haven
8
29.6 mi into trip|~50m in
Take the exit toward Bronx Parkway, Sprain Parkway
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 6
Toward Bronx Parkway, Sprain Parkway
8
29.8 mi into trip|~50m in
Keep slight right at fork toward Bronx Parkway North, Sprain Parkway
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left / slight right lanes.
Toward Bronx Parkway North, Sprain Parkway
8
44.9 mi into trip|~1h 11m in
Take the exit toward NY 9A, NY 100 North
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 5
Toward NY 9A, NY 100 North
Fuel & Cost
Regular Gas
$17.55 one way
$35.09 round trip
$4.18/gal25.4 MPG avg37 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.52
$18.97
$37.95
premium
$4.92
$20.66
$41.32
diesel
$5.61
$23.54
$47.07
Estimated Tolls: $6.69
Throgs Neck Bridge
$6.55
New England Thruway
(2 mi)$0.14
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
$18
Tolls
$7
Meals
$25–$50
Total
$49–$74
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 37.3 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $11 in charging
· 0 stops
· 68% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
32
0
$11.19
$5.12
Efficient EV
26.7
0
$9.33
$4.26
EV Truck/SUV
42.6
0
$14.92
$6.82
Gas CO2
37 kg
EV CO2
12 kg (68% 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 20, 2026
Origin
Oyster Bay, NY
Morning
in Oyster Bay on Tuesday
Local time
6:37 AM
EDT
Current temp
58°F
Unavailable
Live forecast
Destination
Rhinebeck, NY
Morning
in Rhinebeck on Tuesday
Local time
6:37 AM
EDT
Current temp
60°F
Unavailable
Live forecast
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
2h 38m on the road
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
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...
7 mi from route
~19 min detour
Free
near mile 22.1
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...
7 mi from route
~16 min detour
Free
near mile 22.1
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...
12 mi from route
~31 min detour
Free
near mile 18.4
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...
12 mi from route
~29 min detour
Free
near mile 22.1
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...
13 mi from route
~33 min detour
Free
near mile 18.4
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...
13 mi from route
~32 min detour
Free
near mile 18.4
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This route is characterized as a 'Turn-heavy local drive', with only 20% of the journey on highways. You'll navigate a series of local roads, including significant portions of Albany Post Road and NY 9A. The longest uninterrupted stretch you'll encounter is 33.7 miles on Albany Post Road. Be prepared for a driving experience that requires attention to navigation due to the numerous turns involved, rather than a consistent speed on a major highway.
Only 20% highway — the rest is turn-by-turn surface driving.
37 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 33.7 mi on Albany Post Road.
How Hard Is This Drive?
10/10
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 17.6 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 106.6 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 17.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 20.7 miles (I 695 / Throgs Neck Expressway): Highway fork - watch signs carefully. Lane positioning matters here; at 29.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
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 Rhinebeck, NY, road signs point toward Cross Island Parkway North, Bronx, New England, Cross County Parkway West, Bronx Parkway North and Fishkill.
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.
Top landmarks
•Christ Church — historic Episcopal parish in Oyster Bay, New York, USA
Rhinebeck is a township in Dutchess County, New York. The township encompasses the village of Rhinebeck and the hamlet of Rhinecliff. The downtown area of Rhinebeck is small enough to walk around within an hour or so, exclusive of extra time to visit churches and shops, have a meal, etc., and well worth it, as it is full of beautiful, lovingly decorated houses. It also has a beautifully preserved, functioning Roosevelt-era post office with murals that depict the history of the area and other interesting documentation.
Top landmarks
•Rhinebeck Village Historic District — historic district in New York state, USA
•United States Post Office — government building in Rhinebeck, New York
Doable as a same-day drive at 2h 38m. Total distance: 106.6 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
2h 38m drive, comfortable solo distance.
Scenic Drive
Mostly surface roads route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 33.7 miles on Albany Post Road. The full list of main roads is in the Roads section above.
Expect about $6.69 in tolls one way, starting with Throgs Neck Bridge. Most Northeast and Midwest toll agencies accept E-ZPass; in the West and Texas, transponders like TxTag or FasTrak apply. If you do not have a transponder, cashless tolling plates will mail a bill to the vehicle's registered address — usually with a surcharge, so a rental-car toll pass is often cheaper than paying by mail.
Yes — we found about 2 rest areas or service plazas within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Rhinebeck, NY before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 1 meaningful breaks. There are 2 rest areas along the route for bathroom stops.
The main spots that need attention: at 17.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one; at 20.7 miles (I 695 / Throgs Neck Expressway): Highway fork - watch signs carefully. Lane positioning matters here; at 29.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — General Grant National Memorial, Hamilton Grange National Memorial and African Burial Ground National Monument (6 total within detour distance). See the National Parks section for detour distances and tips on detours.
Yes. A round trip is manageable in a single day if you plan a break at Rhinebeck, NY before heading back.
