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How to get fromOakville to Winchesterby train, plane, bus, car, taxi, shuttle, or train (Amtrak)

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There are 11 ways to get from Oakville to Winchester by train, plane, bus, car, taxi, shuttle, or train (Amtrak)

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 to Toronto Island Airport, fly to Washington Dulles International Airport, bus

    best
    1. Take the train from Oakville GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Washington Dulles International Airport (IAD)plane plane YTZ - IAD
    3. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    6h 47m
    $184–631

  2. Drive 390.6 mi

    cheapest
    1. Drive from Oakville to Winchestercar car 390.6 mi
    8h 21m
    $90–130

  3. Train, bus

    1. Take the train from Oakville to New York Penn Stationtrain train VIA Rail
    2. Take the bus from New York to Winchesterbus bus Nyc
    18h 15m
    $209–414

  4. Bus

    1. Take the bus from Mississauga to New Yorkbus bus Adt N801 / ...
    2. Take the bus from New York to Winchesterbus bus Nyc
    18h 45m
    $137–413

  5. Train to Toronto Pearson International Airport, fly to Washington Dulles International Airport, bus, taxi

    1. Take the train from Oakville GO to Union Station GOtrain train
    2. Fly from Toronto Pearson International Airport (YYZ) to Washington Dulles International Airport (IAD)plane plane YYZ - IAD
    3. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    4. Take the taxi from Front Royal Walmart to Winchestertaxi taxi
    7h 18m
    $614–1,181

  6. Fly Toronto Pearson International Airport to Ronald Reagan Washington National Airport, bus

    1. Fly from Toronto Pearson International Airport (YYZ) to Ronald Reagan Washington National Airport (DCA)plane plane YYZ - DCA
    2. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    8h 18m
    $560–1,973

  7. Shuttle to Buffalo Niagara International Airport, fly to Washington Dulles International Airport, bus

    1. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Washington Dulles International Airport (IAD)plane plane BUF - IAD
    3. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    8h 37m
    $214–601

  8. Shuttle to Buffalo Niagara International Airport, fly to Ronald Reagan Washington National Airport, bus

    1. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Ronald Reagan Washington National Airport (DCA)plane plane BUF - DCA
    3. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    9h 35m
    $235–793

  9. Train

    1. Take the train from Oakville to Buffalotrain train
    2. Take the train from Buffalo Depew Station to Cleveland Amtraktrain train
    3. Take the train from Cleveland Amtrak to Martinsburg Amtrak Stationtrain train
    18h 34m
    $246–601

  10. Train, taxi

    1. Take the train from Oakville to New York 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
    19h 6m
    $270–558

  11. Bus, train

    1. Take the bus from Toronto to Buffalobus bus
    2. Take the bus from Buffalo, Ny to Pittsburgh, Pabus bus 530
    3. Take the train from Pittsburgh Amtrak Station to Martinsburg Amtrak Stationtrain train
    20h 31m
    $191–472

Toronto Island Airport (YTZ) to Washington Dulles International Airport (IAD) flights

Calendar21Weekly Planes
Duration1h 25mAverage Duration
Ticket$50Cheapest Price
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Questions & Answers

Map of how to get from Oakville to Winchester.ExpandLaunch map view
  • Distance: 435.7 mi
  • Duration: 6h 47m

What companies run services between Oakville, ON, Canada and Winchester, VA, USA?

You can take a bus from Oakville GO Bus to Winchester via Erin Mills Transitway Station, Erin Mills Station West Platform 4, Mississauga, New York, 42 St-Times Square, Canal St, New York, and Winchester in around 18h 45m. Alternatively, you can take a train from Oakville to Winchester via Buffalo Depew Station, Cleveland Amtrak, and Martinsburg Amtrak Station in around 18h 34m.

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