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How to get fromMontauk to Gloucesterby ferry, train, car, car ferry, or plane

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There are 6 ways to get from Montauk to Gloucester by ferry, train, car, car ferry, or plane

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

  1. Ferry, train

    best
    1. Take the ferry from Montauk to New Londonferry ferry
    2. Take the train from New London to Bostontrain train
    3. Take the train from North Station to Gloucestertrain train
    6h 15m
    $94–160

  2. Drive, car ferry

    cheapest
    1. Drive from Montauk to Orient Pointcar car
    2. Take the carferry from Orient Point to New Londoncarferry car ferry
    3. Drive from New London to Gloucestercar car
    5h 57m
    $50–144

  3. Train to John F. Kennedy International Airport, fly, train

    1. Take the train from Montauk to Jamaicatrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Boston Logan Airport (BOS)plane plane JFK - BOS
    3. Take the train from Chelsea to Gloucestertrain train
    7h 44m
    $240–1,084

  4. Drive, train

    1. Drive from Montauk to New Londoncar car
    2. Take the train from New London to Bostontrain train
    3. Take the train from North Station to Gloucestertrain train
    8h 31m
    $78–143

  5. Train to Long Island Mac Arthur Airport, fly, train

    1. Take the train from Montauk to Patchoguetrain train
    2. Fly from Long Island Mac Arthur Airport (ISP) to Boston Logan Airport (BOS)plane plane ISP - BOS
    3. Take the train from Chelsea to Gloucestertrain train
    7h 25m
    $275–405

  6. Train to Laguardia Airport, fly, train

    1. Take the train from Montauk to Jamaicatrain train
    2. Fly from Laguardia Airport (LGA) to Boston Logan Airport (BOS)plane plane LGA - BOS
    3. Take the train from Chelsea to Gloucestertrain train
    8h 16m
    $79–418

John F. Kennedy International Airport (JFK) to Boston Logan Airport (BOS) flights

Calendar99Weekly Planes
Duration1h 28mAverage Duration
Ticket$37Cheapest Price
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Questions & Answers

Map of how to get from Montauk to Gloucester.ExpandLaunch map view
  • Distance: 162.6 mi
  • Duration: 6h 15m

What companies run services between Montauk, NY, USA and Gloucester, MA, USA?

There is no direct connection from Montauk to Gloucester. However, you can take the taxi to Montauk, take the ferry to New London, walk to New London, take the train to Boston, walk to Back Bay, take the subway to North Station, walk to North Station, then take the train to Gloucester. Alternatively, you can take a vehicle from Montauk to Gloucester via Orient Point and New London in around 5h 57m.

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Train operators
Ferry operators

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