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

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There are 10 ways to get from Waterbury 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 Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport to Grand Central Terminaltrain train
    3. Take the bus from New York to Winchesterbus bus Nyc
    8h 38m
    $92–135

  2. Drive 363.1 mi

    cheapest
    1. Drive from Waterbury to Winchestercar car 363.1 mi
    6h 54m
    $67–96

  3. Train, taxi

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from Ny Moynihan Train Hall At Penn Station to Washington Union Stationtrain train
    4. Take the train from Washington Union Station to DUFFIELDS W VA MARC wbtrain train
    5. Take the taxi from DUFFIELDS W VA MARC wb to Winchestertaxi taxi
    9h 43m
    $161–295

  4. Bus to Bradley International Airport, fly to Washington Dulles International Airport, bus

    1. Take the bus from W Main St @ Leavenworth St to Central Row South Side @ Travelersbus bus
    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
    6h 43m
    $111–422

  5. Bus

    1. Take the bus from W Main St @ Leavenworth St to Asylum St @ Bushnell Parkbus bus 928
    2. Take the bus from Hartford to New Yorkbus bus
    3. Take the bus from New York to Winchesterbus bus Nyc
    10h 19m
    $92–164

  6. Bus to Bradley International Airport, fly to Ronald Reagan Washington National Airport, bus

    1. Take the bus from W Main St @ Leavenworth St to Central Row South Side @ Travelersbus bus
    2. Fly from Bradley International Airport (BDL) to Ronald Reagan Washington National Airport (DCA)plane plane BDL - DCA
    3. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    7h 39m
    $132–564

  7. Train, train to Laguardia Airport, fly to Charlottesville, drive

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport to 125th Street - Harlemtrain train
    3. Fly from Laguardia Airport (LGA) to Charlottesville (CHO)plane plane LGA - CHO
    4. Drive from Charlottesville (CHO) to Winchestercar car
    7h 39m
    $104–461

  8. Train, train to Laguardia Airport, fly to Washington Dulles International Airport, bus

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport to 125th Street - Harlemtrain train
    3. Fly from Laguardia Airport (LGA) to Washington Dulles International Airport (IAD)plane plane LGA - IAD
    4. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    8h 4m
    $142–511

  9. Bus to Bradley International Airport, fly to Baltimore-Washington International Airport, train, taxi

    1. Take the bus from W Main St @ Leavenworth St to Central Row South Side @ Travelersbus bus
    2. Fly from Bradley International Airport (BDL) to Baltimore-Washington International Airport (BWI)plane plane BDL - BWI
    3. Take the train from BWI Thurgood Marshall to Washington Union Stationtrain train
    4. Take the train from Washington Union Station to DUFFIELDS W VA MARC wbtrain train
    5. Take the taxi from DUFFIELDS W VA MARC wb to Winchestertaxi taxi
    8h 38m
    $122–1,039

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

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Fly from Newark Liberty International Airport (EWR) to Washington Dulles International Airport (IAD)plane plane EWR - IAD
    4. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    8h 34m
    $547–1,658

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

Calendar28Weekly Planes
Duration1h 27mAverage Duration
Ticket$53Cheapest Price
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Questions & Answers

Map of how to get from Waterbury to Winchester.ExpandLaunch map view
  • Distance: 423.3 mi
  • Duration: 8h 38m

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

You can take a bus from W Main St @ Leavenworth St to Winchester via Asylum St @ Bushnell Park, Hartford, New York, 42 St-Times Square, Canal St, New York, and Winchester in around 10h 19m.

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