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How to get fromConnecticut to Winchesterby train, bus, taxi, car, or plane

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There are 9 ways to get from Connecticut to Winchester by train, bus, taxi, car, 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, bus

    best
    1. Take the train from Bridgeport to Grand Central Terminaltrain train New Haven
    2. Take the bus from New York to Winchesterbus bus Nyc
    7h 29m
    $82–118

  2. Drive 333.5 mi

    cheapest
    1. Drive from Bridgeport to Winchestercar car 333.5 mi
    6h 20m
    $61–88

  3. Train, taxi

    1. Take the train from Bridgeport Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Washington Union Stationtrain train
    3. Take the train from Washington Union Station to DUFFIELDS W VA MARC wbtrain train
    4. Take the taxi from DUFFIELDS W VA MARC wb to Winchestertaxi taxi
    7h 51m
    $151–276

  4. Fly Bradley International Airport to Washington Dulles International Airport, bus

    1. Fly from Bradley International Airport (BDL) to Washington Dulles International Airport (IAD)plane plane BDL - IAD
    2. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    5h 19m
    $110–396

  5. Fly Bradley International Airport to Ronald Reagan Washington National Airport, bus

    1. Fly from Bradley International Airport (BDL) to Ronald Reagan Washington National Airport (DCA)plane plane BDL - DCA
    2. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    6h 15m
    $131–548

  6. Train to Laguardia Airport, fly to Washington Dulles International Airport, bus

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Washington Dulles International Airport (IAD)plane plane LGA - IAD
    3. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    6h 23m
    $126–467

  7. Train to Newark Liberty International Airport, fly to Washington Dulles International Airport, bus

    1. Take the train from Stamford Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Fly from Newark Liberty International Airport (EWR) to Washington Dulles International Airport (IAD)plane plane EWR - IAD
    3. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    6h 15m
    $526–2,152

  8. Train to John F. Kennedy International Airport, fly to Washington Dulles International Airport, bus

    1. Take the train from Stamford to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Washington Dulles International Airport (IAD)plane plane JFK - IAD
    3. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    6h 48m
    $1,033–1,308

  9. Fly Westchester County Airport to Ronald Reagan Washington National Airport, bus

    1. Fly from Westchester County Airport (HPN) to Ronald Reagan Washington National Airport (DCA)plane plane HPN - DCA
    2. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    7h 40m
    $154–722

Bradley International Airport (BDL) to Washington Dulles International Airport (IAD) flights

Calendar28Weekly Planes
Duration1h 27mAverage Duration
Ticket$51Cheapest Price
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Questions & Answers

Map of how to get from Connecticut to Winchester.ExpandLaunch map view
  • Distance: 391.4 mi
  • Duration: 7h 29m

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

There is no direct connection from Connecticut to Winchester. However, you can take the train to Grand Central Terminal, walk to 42 St-Bryant Park, take the subway to East Broadway, walk to New York, take the bus to Winchester, then take the taxi to Winchester. Alternatively, you can take the train to Ny Moynihan Train Hall At Penn Station, take the train to Washington Union Station, take the train to DUFFIELDS W VA MARC wb, then take the taxi to Winchester.

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