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

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There are 9 ways to get from Stamford 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 Stamford to Grand Central Terminaltrain train New Haven / ...
    2. Take the bus from New York to Winchesterbus bus Nyc
    6h 59m
    $77–111

  2. Drive 312.2 mi

    cheapest
    1. Drive from Stamford to Winchestercar car 312.2 mi
    5h 54m
    $57–83

  3. Train, taxi

    1. Take the train from Stamford 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 24m
    $140–789

  4. 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

  5. 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

  6. Train to Laguardia Airport, fly to Ronald Reagan Washington National Airport, bus

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Ronald Reagan Washington National Airport (DCA)plane plane LGA - DCA
    3. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    7h 15m
    $147–639

  7. 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

  8. Train to John F. Kennedy International Airport, fly to Ronald Reagan Washington National Airport, bus

    1. Take the train from Stamford to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Ronald Reagan Washington National Airport (DCA)plane plane JFK - DCA
    3. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    7h 39m
    $979–2,600

  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 35m
    $154–722

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

Calendar28Weekly Planes
Duration1h 30mAverage Duration
Ticket$55Cheapest Price
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Questions & Answers

Map of how to get from Stamford to Winchester.ExpandLaunch map view
  • Distance: 368.9 mi
  • Duration: 6h 59m

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

There is no direct connection from Stamford 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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