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How to get fromPortland to Winchesterby plane, bus, train, car, taxi, bus (Amtrak, Flixbus), or bus (Amtrak)

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There are 8 ways to get from Portland to Winchester by plane, bus, train, car, taxi, bus (Amtrak, Flixbus), or bus (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. Fly to Washington Dulles International Airport, bus

    best
    1. Fly from Portland (PWM) to Washington Dulles International Airport (IAD)plane plane PWM - IAD
    2. Take the bus from Dulles International Airport to Front Royal Walmartbus bus
    4h 7m
    $135–515

  2. Drive 584.3 mi

    cheapest
    1. Drive from Portland to Winchestercar car 584.3 mi
    10h 49m
    $107–154

  3. Bus, train

    1. Take the bus from Portland, ME to Boston, MA - South Stationbus bus
    2. Take the train from Boston to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the bus from New York to Winchesterbus bus Nyc
    12h 25m
    $137–887

  4. Train, bus

    1. Take the train from Portland to Bostontrain train
    2. Take the train from Boston to Washington Union Stationtrain train
    3. Take the bus from Washington Union Station to Front Royal Walmartbus bus
    14h 6m
    $229–443

  5. Fly to Ronald Reagan Washington National Airport, bus

    1. Fly from Portland (PWM) to Ronald Reagan Washington National Airport (DCA)plane plane PWM - DCA
    2. Take the bus from I St NW @ 15th St NW to Crooked Run Park & Ridebus bus
    5h 9m
    $166–706

  6. Fly to Baltimore-Washington International Airport, train, taxi

    1. Fly from Portland (PWM) to Baltimore-Washington International Airport (BWI)plane plane PWM - BWI
    2. Take the train from BWI Thurgood Marshall 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
    5h 56m
    $150–1,144

  7. Bus

    1. Take the bus from Portland, ME to Boston, MA - South Stationbus bus
    2. Take the bus from Boston to NYC Downtownbus bus
    3. Take the bus from New York to Winchesterbus bus Nyc
    13h 14m
    $114–189

  8. Bus via New York

    1. Take the bus from Portland, ME to Boston, MA - South Stationbus bus
    2. Take the bus from South Station to Port Authority Bus Terminalbus bus
    3. Take the bus from New York to Winchesterbus bus Nyc
    13h 16m
    $127–247

Portland (PWM) to Washington Dulles International Airport (IAD) flights

Calendar33Weekly Planes
Duration2h 14mAverage Duration
Ticket$77Cheapest Price
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Questions & Answers

Map of how to get from Portland to Winchester.ExpandLaunch map view
  • Distance: 565.9 mi
  • Duration: 4h 7m

What companies run services between Portland, ME, USA and Winchester, VA, USA?

You can take a bus from Portland, ME to Winchester via Boston, MA - South Station, Boston, NYC Downtown, New York, and Winchester in around 13h 14m.

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