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

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There are 11 ways to get from Portland to Westport by plane, train, train (Amtrak), bus (Flixbus, Greyhound), or car

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 John F. Kennedy International Airport, train

    best
    1. Fly from Portland International Airport (PDX) to John F. Kennedy International Airport (JFK)plane plane PDX - JFK
    2. Take the train from Grand Central Terminal to Darientrain train
    10h 2m
    $242–595

  2. Fly to Long Island Mac Arthur Airport, train

    cheapest
    1. Fly from Portland International Airport (PDX) to Long Island Mac Arthur Airport (ISP)plane plane PDX - ISP
    2. Take the train from Central Islip to Grand Central Terminaltrain train
    3. Take the train from Grand Central Terminal to Darientrain train
    14h 43m
    $203–757

  3. Train via Chicago

    1. Take the train from Portland to Chicago Union Stationtrain train
    2. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train
    3. Take the train from Croton-Harmon to 125th Street - Harlemtrain train
    4. Take the train from 125th Street - Harlem to Westporttrain train
    2d 20h
    $894–1,990

  4. Bus

    1. Take the bus from Portland Curbside Bus Stop to Pasco Bus Stopbus bus
    2. Take the bus from Pasco Bus Stop to Denver Union Stationbus bus
    3. Take the bus from Denver Union Station to Chicago Bus Stationbus bus
    4. Take the bus from Chicago Bus Station to New York Midtownbus bus
    5. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus
    2d 23h
    $460–845

  5. Drive 2,918.7 mi

    1. Drive from Portland to Westportcar car 2,918.7 mi
    46h 57m
    $533–770

  6. Fly to Laguardia Airport, train

    1. Fly from Portland International Airport (PDX) to Laguardia Airport (LGA)plane plane PDX - LGA
    2. Take the train from 125th Street - Harlem to Darientrain train
    11h 22m
    $240–934

  7. Fly to Newark Liberty International Airport, train

    1. Fly from Portland International Airport (PDX) to Newark Liberty International Airport (EWR)plane plane PDX - EWR
    2. Take the train from Newark Liberty International Airport to Bridgeport Amtrak Stationtrain train
    10h 53m
    $224–700

  8. Fly to Westchester County Airport

    1. Fly from Portland International Airport (PDX) to Westchester County Airport (HPN)plane plane PDX - HPN
    13h 14m
    $205–825

  9. Fly to Philadelphia International Airport, train

    1. Fly from Portland International Airport (PDX) to Philadelphia International Airport (PHL)plane plane PDX - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from Ny Moynihan Train Hall At Penn Station to Bridgeport Amtrak Stationtrain train
    12h 22m
    $253–1,043

  10. Fly to Boston Logan Airport, train

    1. Fly from Portland International Airport (PDX) to Boston Logan Airport (BOS)plane plane PDX - BOS
    2. Take the train from Boston to Bridgeport Amtrak Stationtrain train
    12h 19m
    $269–614

  11. Train

    1. Take the train from Portland to Vancouvertrain train
    2. Take the train from Vancouver to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Yonkerstrain train
    4d 22h
    $996–2,109

Portland to Westport by bus and foot

Calendar7Weekly Services
Duration2d 23hAverage Duration
Ticket$460Cheapest Price
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Questions & Answers

Map of how to get from Portland to Westport.ExpandLaunch map view
  • Distance: 2,522.9 mi
  • Duration: 10h 2m

What companies run services between Portland, OR, USA and Westport, CT, USA?

You can take a train from Portland to Westport via Chicago Union Station, Croton-Harmon, 125th Street - Harlem, and Westport in around 2d 20h. Alternatively, you can take a bus from Portland Curbside Bus Stop to Post Rd. West at Myrtle Ave. via Pasco Bus Stop, Denver Union Station, Chicago Bus Station, New York Midtown, Port Authority Bus Terminal, and Bridgeport Transportation Center in around 2d 23h.

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