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How to get fromWinchester to Connecticutby train (Amtrak), car, plane, or train

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There are 4 ways to get from Winchester to Connecticut by train (Amtrak), car, plane, or train

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 (Amtrak)

    best
    1. Take the train from Boston to Bridgeport Amtrak Stationtrain train Northeast Regional
    4h 12m
    $59–130

  2. Drive 152.8 mi

    cheapest
    1. Drive from Winchester to Bridgeportcar car 152.8 mi
    2h 51m
    $28–41

  3. Fly to Laguardia Airport, train

    1. Fly from Boston Logan Airport (BOS) to Laguardia Airport (LGA)plane plane BOS - LGA
    2. Take the train from 125th Street - Harlem to Stamfordtrain train
    4h 56m
    $78–430

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

    1. Fly from Boston Logan Airport (BOS) to John F. Kennedy International Airport (JFK)plane plane BOS - JFK
    2. Take the train from Grand Central Terminal to Stamfordtrain train
    5h 24m
    $235–1,051

Winchester to Connecticut by train and subway (Amtrak)

Calendar60Weekly Services
Duration4h 12mAverage Duration
Ticket$59Cheapest Price
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Questions & Answers

Map of how to get from Winchester to Connecticut.ExpandLaunch map view
  • Distance: 181.6 mi
  • Duration: 4h 12m

What companies run services between Winchester, MA, USA and Connecticut, USA?

Amtrak operates a train from Boston to Bridgeport Amtrak Station every 3 hours. Tickets cost $55–120 and the journey takes 2h 41m.

Airlines
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