Oak Bluffs to Ossining runs about 5 times a day, with the first departure around 06:09 and the last around 07:30. One passenger pays €17.39, every fee included. The fastest door to door is 10h over 291 km, on services run by 1 operator across 1 mode.
What one seat costs
Every operator we hold on this corridor starts at €17.39, so there is no spread to show.
Typical fares · Priced for October 5, 2026
€17.39
- 164%Moves across the booking window
When it runs, leaving Oak Bluffs
No operator has filed a timetable for this direction yet, so the first and last departure below follow the pattern of the corridor. Read them as the shape of the service day rather than as times to turn up for.
- 06:09First departure
- 07:30Last departure
- 5Services per day
- 20%Run direct
Seastreak runs this service and does not sell it here. Bookaway takes the payment.
Buying this trip
Bookaway lists departures for Oak Bluffs to Ossining on your date, and you pay on their side.
See Oak Bluffs to Ossining on Bookaway
Partner link. We do not sell this ticket, and we earn nothing from this one.
Fares by date
What this journey usually costs, by departure date. It shows which days run dearer.
Typical fares
- about €48.74Fri18
- about €46.53Sat19
- about €41.04Sun20
- about €30.59Mon21
- about €31.14Tue22
- about €31.14Wed23
- about €36.09Thu24
- about €29.49Fri25
- about €26.74Sat26
- about €26.74Sun27
- about €21.79Mon28
- about €25.64Tue29
- about €25.09Wed30
- about €32.24Thu1
- about €26.19Fri2
- about €27.84Sat3
- about €20.69Sun4
- about €17.39Mon5
- about €21.24Tue6
- about €23.44Wed7
- about €22.89Thu8
Based on what this route has cost recently. The operator sets the price on the day, and the live fare is confirmed when you book.
The ferry gets you into Ossining. It does not get you a bed, and neither do we.
A room in Ossining for the night the ferry gets in
Sort by distance from Ossining station and you can see which places are ten minutes on foot and which are not.
Search Ossining on Booking.comOr compare on Expedia
Partner links. We do not sell accommodation. We earn a commission when a booking completes, and it never changes what you pay.
When to book Oak Bluffs to Ossining
The same search run across the whole booking window, so the shape of the curve is visible rather than described.
- €22.3390 days
- €18.4960 days
- €19.5945 days
- €22.3330 days
- €22.8921 days
- €32.2414 days
- €36.097 days
- €41.043 days
- €48.741 days
- Cheapest lead time
- Fares bottom out around 60 days ahead, at €18.49.
- How much it moves
- The gap between the cheapest and most expensive lead time is 164 percent. The most expensive point is €48.74, 1 days out.
- What that means
- Today sits inside the cheap window, which closes about 60 days before departure. Waiting from here has usually cost money on this corridor rather than saved it.
Book now Fares on this route are lowest around 60 days ahead. You are inside that window.
This corridor, specifically
Facts that apply to Oak Bluffs to Ossining and to no other route on the site.
Clocks
Both ends keep the same time, so the arrival is the departure plus the journey.
The shape of it
291 km
277 km as the crow flies, 5% further by the route services take. The bearing runs west.
Who lives at each end
3,778 → 25,441
Population at the departure city and at the arrival city, which is usually what decides how often anything runs.
How we know
0/2
2 of these connections were inferred from service-area overlap rather than observed in a timetable. We would rather say so.
The route
What the journey looks like
Direct or connecting, how far the route really runs, and what happens when a connection is missed.
- Direct or connecting
- 20% of the services we sell on this corridor run through without a change. The remaining 80% involve one connection.
- How far it really runs
- The route covers 291 km against 277 km in a straight line, a detour of 5 percent. Track and road geometry account for the difference.
- Where the change is
- Connections are made at New London, South Kingstown, Bridgeport, Branford. The gap between arriving and leaving is 59 minutes, of which about 5 is walking.
- If the connection is missed
- The tightest connection we sell here has a 16 percent chance of not being made on the timetable alone. Both legs are sold on one booking, so a missed connection is ours to fix and you are rebooked at no charge.
Who runs this route
Ossining is small enough to see in an afternoon, which is easier without the luggage. Storing it is not our business.
Baggage storage near Ossining station
Most of the points near Ossining station open before the first train and close after the last one.
Check Ossining on StasherOr try Bounce
Partner links. We do not run these networks. We earn a commission on a booking, and the price is the same as going direct.
Questions about Oak Bluffs to Ossining
The questions people actually ask about this trip, answered from the same prices and times the page above is built on rather than written once and left to go stale.
How long does it take to get from Oak Bluffs to Ossining?
The fastest journey from Oak Bluffs to Ossining takes 10h door to door, of which 9h 51m is spent moving, on the ferry. Most services take around 10h 33m, because that average includes slower stopping services and journeys with a connection. Times include reaching the terminal and leaving it at the far end.
How much does it cost to travel from Oak Bluffs to Ossining?
The cheapest fare from Oak Bluffs to Ossining is €17.39, as of September 17, 2026. A typical fare across the next three weeks is €26.74. Both figures are the total for one passenger, including taxes, supplier fees and our service fee, so nothing is added at checkout.
What is the cheapest way to get from Oak Bluffs to Ossining?
The cheapest way from Oak Bluffs to Ossining is by ferry, at €17.39 for one passenger on October 5, 2026. That journey takes 11h 21m door to door. Cheaper is rarely faster on this corridor, and the comparison table on this page shows what each mode costs against what it saves.
When should I book Oak Bluffs to Ossining?
Fares from Oak Bluffs to Ossining bottom out around 60 days before departure, at €18.49. Across the whole booking window the gap between the cheapest and the most expensive lead time is 164 percent, measured on September 17, 2026. Booking inside the last week has consistently cost more on this corridor.
Which day of the week is cheapest for Oak Bluffs to Ossining?
Monday is the cheapest day to depart from Oak Bluffs to Ossining, at €21.79. That is the median of 21 priced departure days across the next three weeks, as of September 17, 2026. Shifting a departure by one day is usually worth more than shifting the booking by one week.
Which month is cheapest for Oak Bluffs to Ossining?
February is the cheapest of the next 5 months to travel from Oak Bluffs to Ossining, at €14.64 for one passenger. Each month is priced on its fifteenth, so the comparison is like for like rather than a mix of weekends and midweek departures.
Who runs service from Oak Bluffs to Ossining?
No operator record names Oak Bluffs to Ossining directly. Seastreak publish service areas covering both ends and may serve it, so we list them as possible operators rather than confirmed ones.
Is there a direct service from Oak Bluffs to Ossining?
20 percent of the services we sell from Oak Bluffs to Ossining are direct. The rest connect at New London, South Kingstown, Bridgeport, Branford, with about 59 minutes between the two services. Both legs are sold on one booking, so a missed connection is rebooked at no charge.
Which station or terminal do services from Oak Bluffs to Ossining use?
Services from Oak Bluffs to Ossining by ferry leave from Falmouth-Edgartown Ferry and arrive at Ossining. Allow about 1h 30m in total for reaching the departure terminal and leaving the arrival one, which is already included in every door to door time on this page.
Can I change or refund a ticket from Oak Bluffs to Ossining?
1 of the 1 operators we sell from Oak Bluffs to Ossining allow a change or a refund. A change on a changeable fare costs €5.00. The operator table on this page names which is which, and the condition is shown again before you pay.
Where these numbers come from
Places, coordinates, operators, which operator serves which pair, and every distance on this page are real and come from open data. Where a corridor has a filed timetable the departure times are real too, and ferry fares are the prices the operators publish themselves.
Derived from service area No carrier record names this exact pair. The operators listed publish a service area covering both places at a distance their mode plausibly carries people, which is evidence that the corridor is served and not evidence of a specific service. Pages state which, because presenting the two as the same thing would be dishonest.
Where no operator publishes a fare for a corridor, the price here is our own estimate, worked out from the real distance and the real operator through a fare curve that follows lead time, day of the week and season. It tells you roughly what the journey costs. It is not a seat anyone has agreed to sell, and the payment step will not take it.
Defined in full at Door to door, Fares, The booking window, Carbon, Distances
- On this page
- Every figure above was computed for Oak Bluffs to Ossining on September 17, 2026: 291 km of route against 277 km in a straight line, 5 services a day, 1 operator a cheapest fare of €17.39, and 10h door to door on the fastest mode. The return direction is computed separately and its numbers are not these numbers.
Being on the water gives Ossining a set of days out that do not start at a station. We do not sell those either.
Day trips out of Ossining and across United States
Day trips that leave Ossining in the morning and cover a good part of United States by evening.
See Ossining on GetYourGuideOr browse Viator
Partner links. We do not sell tours or tickets. We earn a commission on a booking, and it never changes the price.
The two ends, compared
Oak Bluffs reaches 21 places in 1 countries on services we hold, over distances from 32 to 300 km. Ossining reaches 21 places in 1 countries, from 35 to 315 km.
Other ways to make this journey
Leaving Oak Bluffs
- 21Places you can leave for
- 1Countries
- 2Operators
Arriving in Ossining
Leaving Ossining
- 21Places you can leave for
- 1Countries
- 1Operators