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How to get fromWinchester to Sleepy Hollowby bus, train, bus (Greyhound), car, taxi, plane, bus (Flixbus), or shuttle

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There are 11 ways to get from Winchester to Sleepy Hollow by bus, train, bus (Greyhound), car, taxi, plane, bus (Flixbus), or shuttle

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, train

    best
    1. Take the bus from Front Royal Walmart to Washington Union Stationbus bus Valley Flyer
    2. Take the train from Washington Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Acela
    7h 30m
    $138–242

  2. Drive 301 mi

    cheapest
    1. Drive from Winchester to Sleepy Hollowcar car 301 mi
    5h 47m
    $55–80

  3. Bus via New York

    1. Take the bus from Front Royal Walmart to Washington Union Stationbus bus Valley Flyer
    2. Take the bus from Union Station to Port Authority Bus Terminalbus bus Washington
    8h 47m
    $115–179

  4. Taxi, bus to Washington Dulles International Airport, fly to Laguardia Airport, train

    1. Take the taxi from Winchester to Front Royal Walmarttaxi taxi
    2. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    3. Fly from Washington Dulles International Airport (IAD) to Laguardia Airport (LGA)plane plane IAD - LGA
    4. Take the train from 125th Street - Harlem to Tarrytowntrain train
    5h 34m
    $126–504

  5. Taxi, train

    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 Ny Moynihan Train Hall At Penn Stationtrain train
    7h 49m
    $144–263

  6. Bus

    1. Take the bus from Crooked Run Park & Ride to 14th St @ F St NWbus bus 611-Fr
    2. Take the bus from Washington Union Station to White Plains Stationbus bus FlixBus 2605
    10h 29m
    $104–142

  7. Taxi, bus to Ronald Reagan Washington National Airport, fly to Laguardia Airport, train

    1. Take the taxi from Winchester to Crooked Run Park & Ridetaxi taxi
    2. Take the bus from Crooked Run Park & Ride to Virginia Ave @ 21st St NWbus bus
    3. Fly from Ronald Reagan Washington National Airport (DCA) to Laguardia Airport (LGA)plane plane DCA - LGA
    4. Take the train from 125th Street - Harlem to Tarrytowntrain train
    6h 6m
    $161–787

  8. Bus to Washington Dulles International Airport, fly to Newark Liberty International Airport, shuttle

    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to Newark Liberty International Airport (EWR)plane plane IAD - EWR
    3. Take a shuttle bus from Newark Airport Terminal B to Grand Centralshuttle bus
    6h 16m
    $553–1,637

  9. Bus to Washington Dulles International Airport, fly to John F. Kennedy International Airport, train

    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to John F. Kennedy International Airport (JFK)plane plane IAD - JFK
    3. Take the train from Grand Central Terminal to Tarrytowntrain train
    5h 44m
    $1,033–1,305

  10. Taxi, bus to Ronald Reagan Washington National Airport, fly to John F. Kennedy International Airport, train

    1. Take the taxi from Winchester to Crooked Run Park & Ridetaxi taxi
    2. Take the bus from Crooked Run Park & Ride to Virginia Ave @ 21st St NWbus bus
    3. Fly from Ronald Reagan Washington National Airport (DCA) to John F. Kennedy International Airport (JFK)plane plane DCA - JFK
    4. Take the train from Jamaica to Grand Central Terminaltrain train
    5. Take the train from Grand Central Terminal to Tarrytowntrain train
    6h 11m
    $978–1,898

  11. Taxi, bus to Ronald Reagan Washington National Airport, fly to Westchester County Airport, line 13 bus

    1. Take the taxi from Winchester to Crooked Run Park & Ridetaxi taxi
    2. Take the bus from Crooked Run Park & Ride to Virginia Ave @ 21st St NWbus bus
    3. Fly from Ronald Reagan Washington National Airport (DCA) to Westchester County Airport (HPN)plane plane DCA - HPN
    4. Take the bus from White Plains Bus Terminal Lane F to Wildey St @ Valley Stbus bus
    7h 10m
    $156–721

Washington Dulles International Airport (IAD) to Laguardia Airport (LGA) flights

Calendar28Weekly Planes
Duration1h 25mAverage Duration
Ticket$59Cheapest Price
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Questions & Answers

Map of how to get from Winchester to Sleepy Hollow.ExpandLaunch map view
  • Distance: 352.1 mi
  • Duration: 7h 30m

What companies run services between Winchester, VA, USA and Sleepy Hollow, NY, USA?

You can take a vehicle from Winchester to Tarrytown via Front Royal Walmart, Union Station, Port Authority Bus Terminal, West 42nd Street & 8th Avenue, E 42 St/Madison Av, and Grand Central Terminal in around 8h 47m.

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