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

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There are 9 ways to get from Bridgeport 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. Train to Laguardia Airport, fly to Charlottesville, drive

    1. Take the train from Bridgeport to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Charlottesville (CHO)plane plane LGA - CHO
    3. Drive from Charlottesville (CHO) to Winchestercar car
    6h 28m
    $93–444

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

    1. Take the train from Bridgeport 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 53m
    $131–474

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

    1. Take the train from Bridgeport 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 42m
    $537–1,639

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

    1. Take the train from Bridgeport 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
    7h 18m
    $1,038–1,315

  8. Train to Bradley International Airport, fly to Washington Dulles International Airport, bus

    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Washington Dulles International Airport (IAD)plane plane BDL - IAD
    3. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    7h 48m
    $129–442

  9. Train, line 971 bus to Westchester County Airport, fly to Ronald Reagan Washington National Airport, bus, taxi

    1. Take the train from Bridgeport to Stamfordtrain train
    2. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus bus
    3. Fly from Westchester County Airport (HPN) to Ronald Reagan Washington National Airport (DCA)plane plane HPN - DCA
    4. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    5. Take the taxi from Crooked Run Park & Ride to Winchestertaxi taxi
    8h 58m
    $160–737

Laguardia Airport (LGA) to Charlottesville (CHO) flights

Calendar27Weekly Planes
Duration1h 57mAverage Duration
Ticket$61Cheapest Price
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Questions & Answers

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

What companies run services between Bridgeport, CT, USA and Winchester, VA, USA?

There is no direct connection from Bridgeport 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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