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How to get fromConnecticut to Winchesterby train (Amtrak), bus (Greyhound, Flixbus), car, train, or plane

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There are 5 ways to get from Connecticut to Winchester by train (Amtrak), bus (Greyhound, Flixbus), 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 (Amtrak)

    best
    1. Take the train from Bridgeport Amtrak Station to Bostontrain train Northeast Regional
    4h 4m
    $59–121

  2. Bus

    cheapest
    1. Take the bus from Bridgeport Bus Stop to Hartford Union Stationbus bus Greyhound US0255s
    2. Take the bus from Hartford Union Station to Bostonbus bus Greyhound US0230 / ...
    5h 22m
    $28–53

  3. Drive 153.1 mi

    1. Drive from Bridgeport to Winchestercar car 153.1 mi
    2h 50m
    $28–41

  4. Train to Laguardia Airport, fly

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Boston Logan Airport (BOS)plane plane LGA - BOS
    5h 29m
    $68–380

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

    1. Take the train from Stamford to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Boston Logan Airport (BOS)plane plane JFK - BOS
    5h 36m
    $235–1,051

Connecticut to Winchester by train, subway, and bus (Amtrak)

Calendar70Weekly Services
Duration4h 4mAverage Duration
Ticket$59Cheapest Price
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Questions & Answers

Map of how to get from Connecticut to Winchester.ExpandLaunch map view
  • Distance: 182.8 mi
  • Duration: 4h 4m

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

Amtrak operates a train from Bridgeport Amtrak Station to Boston every 3 hours. Tickets cost $55–120 and the journey takes 2h 53m. Alternatively, you can take a bus from Bridgeport Bus Stop to Laraway Rd @ Winchester Ctr via Hartford Union Station, Boston, Chinatown, Wellington, and Wellington in around 5h 22m.

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