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How to get fromWinchester to Benningtonby bus, plane, train, bus (Greyhound), car, taxi, or bus (Flixbus)

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There are 7 ways to get from Winchester to Bennington by bus, plane, train, bus (Greyhound), car, taxi, or bus (Flixbus)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Bus to Washington Dulles International Airport, fly, bus

    best
    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to Albany County Airport (ALB)plane plane IAD - ALB
    3. Take the bus from Albany International Airport to Green Mountain Community Bus Terminalbus bus
    6h 42m
    $143–554

  2. Drive 422.6 mi

    cheapest
    1. Drive from Winchester to Benningtoncar car 422.6 mi
    8h 17m
    $78–112

  3. Bus, train

    1. Take the bus from Front Royal Walmart to Washington Union Stationbus bus
    2. Take the train from Washington Union Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from Ny Moynihan Train Hall At Penn Station to Albany-Rensselaer Amtrak Stationtrain train
    4. Take the bus from AMTRAK Station Rensselaer to Green Mountain Community Bus Terminalbus bus 7
    11h 30m
    $184–330

  4. Bus

    1. Take the bus from Front Royal Walmart to Washington Union Stationbus bus
    2. Take the bus from Union Station to Port Authority Bus Terminalbus bus
    3. Take the bus from New York to Albanybus bus
    4. Take the bus from Greyhound \ Trailways Terminal to Green Mountain Community Bus Terminalbus bus 7
    13h 28m
    $139–266

  5. Bus to Ronald Reagan Washington National Airport, fly, bus

    1. Take the bus from Crooked Run Park & Ride to Virginia Ave @ 21st St NWbus bus
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Albany County Airport (ALB)plane plane DCA - ALB
    3. Take the bus from Albany International Airport to Green Mountain Community Bus Terminalbus bus
    7h 23m
    $183–877

  6. Taxi, train, train to Baltimore-Washington International Airport, fly, bus

    1. Take the taxi from Winchester to DUFFIELDS W VA MARC ebtaxi taxi
    2. Take the train from DUFFIELDS W VA MARC eb to Washington Union Stationtrain train
    3. Take the train from Washington Union Station to BWI Thurgood Marshalltrain train
    4. Fly from Baltimore-Washington International Airport (BWI) to Albany County Airport (ALB)plane plane BWI - ALB
    5. Take the bus from Albany International Airport to Green Mountain Community Bus Terminalbus bus
    8h 24m
    $159–1,204

  7. Bus via Washington

    1. Take the bus from Crooked Run Park & Ride to 14th St @ F St NWbus bus
    2. Take the bus from Washington Union Station to New York Midtownbus bus
    3. Take the bus from New York, NY to Albany-Rensselaerbus bus Nyc
    4. Take the bus from AMTRAK Station Rensselaer to Green Mountain Community Bus Terminalbus bus 7
    13h 48m
    $122–198

Washington Dulles International Airport (IAD) to Albany County Airport (ALB) flights

Calendar28Weekly Planes
Duration1h 31mAverage Duration
Ticket$75Cheapest Price
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Questions & Answers

Map of how to get from Winchester to Bennington.ExpandLaunch map view
  • Distance: 449.1 mi
  • Duration: 6h 42m

What companies run services between Winchester, VA, USA and Bennington, VT, USA?

You can take a vehicle from Winchester to Green Mountain Community Bus Terminal via Front Royal Walmart, Union Station, Port Authority Bus Terminal, New York, Albany, and Greyhound \ Trailways Terminal in around 13h 28m.

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