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How to get fromPortland to Ossiningby plane, train, bus, bus (Flixbus), car, train (Amtrak), or bus (Amtrak, Greyhound)

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There are 8 ways to get from Portland to Ossining by plane, train, bus, bus (Flixbus), car, train (Amtrak), or bus (Amtrak, Greyhound)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly to Laguardia Airport, train

    best
    1. Fly from Portland (PWM) to Laguardia Airport (LGA)plane plane PWM - LGA
    2. Take the train from 125th Street - Harlem to Ossiningtrain train
    3h 19m
    $88–505

  2. Drive 287 mi

    cheapest
    1. Drive from Portland to Ossiningcar car 287 mi
    5h 16m
    $53–76

  3. Bus, train

    1. Take the bus from Portland, ME to Boston, MA - South Stationbus bus
    2. Take the train from Boston to Stamford Amtrak Stationtrain train
    3. Take the train from Stamford to 125th Street - Harlemtrain train
    4. Take the train from 125th Street - Harlem to Ossiningtrain train
    8h 5m
    $85–776

  4. Bus (Flixbus)

    1. Take the bus from City of Portland to New York Midtownbus bus FlixBus N2615
    9h 2m
    $66–106

  5. Fly to John F. Kennedy International Airport, train

    1. Fly from Portland (PWM) to John F. Kennedy International Airport (JFK)plane plane PWM - JFK
    2. Take the train from Grand Central Terminal to Ossiningtrain train
    3h 16m
    $69–319

  6. Fly to Newark Liberty International Airport, train

    1. Fly from Portland (PWM) to Newark Liberty International Airport (EWR)plane plane PWM - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Stationtrain train
    4h 14m
    $569–2,053

  7. Train

    1. Take the train from Portland to Bostontrain train
    2. Take the train from Boston to Stamford Amtrak Stationtrain train
    3. Take the train from Stamford to 125th Street - Harlemtrain train
    4. Take the train from 125th Street - Harlem to Ossiningtrain train
    8h 48m
    $104–811

  8. Bus via Boston

    1. Take the bus from Portland, ME to Boston, MA - South Stationbus bus Portland / ...
    2. Take the bus from Boston to White Plains Bus Stationbus bus Greyhound US0240
    9h 27m
    $54–111

Portland to Ossining by bus and train

Calendar118Weekly Services
Duration8h 5mAverage Duration
Ticket$85Cheapest Price
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Questions & Answers

Map of how to get from Portland to Ossining.ExpandLaunch map view
  • Distance: 302.6 mi
  • Duration: 3h 19m

What companies run services between Portland, ME, USA and Ossining, NY, USA?

Flixbus USA operates a bus from City of Portland to New York Midtown once daily. Tickets cost $55–90 and the journey takes 7h 16m. Alternatively, you can take a train from Portland to Ossining via Boston, North Station, Back Bay, Boston, Stamford Amtrak Station, Stamford, and 125th Street - Harlem in around 8h 48m.

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