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How to get fromFairfield to Winchesterby train (Amtrak), car, train, or plane

Find Transport to Winchester

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There are 4 ways to get from Fairfield to Winchester by train (Amtrak), car, train, 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. Train

    best
    1. Take the train from Fairfield to New Haventrain train New Haven
    2. Take the train from New Haven to Bostontrain train Northeast Regional
    5h 16m
    $48–672

  2. Drive 157.6 mi

    cheapest
    1. Drive from Fairfield to Winchestercar car 157.6 mi
    2h 57m
    $29–42

  3. Train to Laguardia Airport, fly

    1. Take the train from Fairfield to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Boston Logan Airport (BOS)plane plane LGA - BOS
    5h 51m
    $72–395

  4. Train to John F. Kennedy International Airport, fly

    1. Take the train from Fairfield to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Boston Logan Airport (BOS)plane plane JFK - BOS
    6h 1m
    $239–1,057

Fairfield to Winchester by train, subway, and bus

Calendar109Weekly Services
Duration5h 16mAverage Duration
Ticket$48Cheapest Price
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Questions & Answers

Map of how to get from Fairfield to Winchester.ExpandLaunch map view
  • Distance: 187.7 mi
  • Duration: 5h 16m

What companies run services between Fairfield, CT, USA and Winchester, MA, USA?

You can take a train from Fairfield to Laraway Rd @ Winchester Ctr via New Haven, Boston, Back Bay, Wellington, and Wellington in around 5h 16m.

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Train operators

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