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

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There are 9 ways to get from Winchester to Portland by bus, plane, train, bus (Flixbus, Greyhound, Amtrak), 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 to Portland

    best
    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to Portland (PWM)plane plane IAD - PWM
    4h 14m
    $125–472

  2. Drive 584.8 mi

    cheapest
    1. Drive from Winchester to Portlandcar car 584.8 mi
    10h 46m
    $107–155

  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 Bostontrain train
    3. Take the bus from Boston, MA - South Station to Portland, MEbus bus
    12h 41m
    $214–421

  4. Bus

    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 Bostonbus bus
    3. Take the bus from Boston, MA - South Station to Portland, MEbus bus
    15h 20m
    $147–249

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

    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 Portland (PWM)plane plane DCA - PWM
    4h 53m
    $165–715

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

    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 Portland (PWM)plane plane BWI - PWM
    5h 54m
    $146–1,092

  7. Bus to Washington Dulles International Airport, fly to Boston Logan Airport, bus

    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to Boston Logan Airport (BOS)plane plane IAD - BOS
    3. Take the bus from Logan International Airport to Portland, MEbus bus
    7h
    $582–1,202

  8. 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
    4. Take the train from Ny Moynihan Train Hall At Penn Station to Bostontrain train
    5. Take the train from Boston to Portlandtrain train
    13h 48m
    $242–470

  9. Bus via New York

    1. Take the bus from Front Royal Walmart to Washington Union Stationbus bus
    2. Take the bus from Washington Union Station to New York Midtownbus bus
    3. Take the bus from New York Midtown to City of Portlandbus bus
    16h 12m
    $153–231

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

Calendar26Weekly Planes
Duration1h 49mAverage Duration
Ticket$68Cheapest Price
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Questions & Answers

Map of how to get from Winchester to Portland.ExpandLaunch map view
  • Distance: 567.3 mi
  • Duration: 4h 14m

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

You can take a vehicle from Winchester to Portland, ME via Crooked Run Park & Ride, 14th St @ F St NW, 13 St NW+F St NW, Massachusetts Av NE+1 St NE, Washington Union Station, Boston, and Boston, MA - South Station in around 15h 20m.

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