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How to get fromPittsburgh to Winchesterby bus, plane, train (Amtrak), car, train, or bus (Greyhound)

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There are 7 ways to get from Pittsburgh to Winchester by bus, plane, train (Amtrak), car, train, or bus (Greyhound)

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 Pittsburgh International Airport, fly to Boston Logan Airport

    best
    1. Take the bus from Seventh Ave + Smithfield St to Pittsburgh International Airportbus bus
    2. Fly from Pittsburgh International Airport (PIT) to Boston Logan Airport (BOS)plane plane PIT - BOS
    5h 27m

  2. Bus

    cheapest
    1. Take the bus from Pittsburgh Greyhound to Port Authority Bus Terminalbus bus Pittsburgh
    2. Take the bus from Manhattan, NY to Cambridge - Alewife Stationbus bus Manhattan-Cambridge
    13h 47m
    $92–135

  3. Train (Amtrak)

    1. Take the train from Pittsburgh Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train Pennsylvanian
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Bostontrain train Acela
    14h 49m
    $221–456

  4. Drive 568.6 mi

    1. Drive from Pittsburgh to Winchestercar car 568.6 mi
    10h 26m
    $104–150

  5. Fly Pittsburgh International Airport to Theodore Francis Green State Airport, train

    1. Fly from Pittsburgh International Airport (PIT) to Theodore Francis Green State Airport (PVD)plane plane PIT - PVD
    2. Take the train from TF Green Airport to Rugglestrain train
    7h 29m
    $150–681

  6. Train to Cleveland-Hopkins International Airport, fly to Boston Logan Airport

    1. Take the train from Pittsburgh Amtrak Station to Cleveland Amtraktrain train
    2. Fly from Cleveland-Hopkins International Airport (CLE) to Boston Logan Airport (BOS)plane plane CLE - BOS
    8h 12m
    $238–1,060

  7. Bus via South Station

    1. Take the bus from Pittsburgh Intermodal Station to Port Authority Bus Terminalbus bus Greyhound US0421 / ...
    2. Take the bus from Port Authority Bus Terminal to South Stationbus bus New York
    16h 1m
    $102–202

Pittsburgh to Winchester by train, subway, and bus (Amtrak)

Calendar7Weekly Services
Duration14h 49mAverage Duration
Ticket$221Cheapest Price
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Questions & Answers

Map of how to get from Pittsburgh to Winchester.ExpandLaunch map view
  • Distance: 540.5 mi
  • Duration: 5h 27m

What companies run services between Pittsburgh, PA, USA and Winchester, MA, USA?

You can take a bus from Pittsburgh Greyhound to Cambridge St @ Church St via Port Authority Bus Terminal, Manhattan, NY, and Alewife in around 13h 47m. Alternatively, you can take a train from Pittsburgh Amtrak Station to Laraway Rd @ Winchester Ctr via Ny Moynihan Train Hall At Penn Station, Boston, Back Bay, Wellington, and Wellington in around 14h 49m.

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