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How to get fromBoston to Chestertownby plane, bus, taxi, train, or car

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There are 10 ways to get from Boston to Chestertown by plane, bus, taxi, train, or car

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 Boston Logan Airport to Baltimore-Washington International Airport, bus, taxi

    best
    1. Fly from Boston Logan Airport (BOS) to Baltimore-Washington International Airport (BWI)plane plane BOS - BWI
    2. Take the bus from BWI-Thurgood Marshall Airport to Kent Island, MDbus bus
    3. Take the taxi from Kent Island, MD to Chestertowntaxi taxi
    3h 59m
    $277–1,116

  2. Drive  376.2 mi

    cheapest
    1. Drive from Boston to Chestertowncar car 376.2 mi
    7h 9m
    $69–100

  3. Train, taxi

    1. Take the train from Boston to Aberdeen Amtrak Stationtrain train Northeast Regional
    2. Take the taxi from Aberdeen Amtrak Station to Chestertowntaxi taxi
    8h 21m
    $214–373

  4. Bus, drive

    1. Take the bus from Boston to New Yorkbus bus
    2. Take the bus from New York to Baltimorebus bus
    3. Drive from Baltimore to Chestertowncar car
    9h 52m
    $101–175

  5. Fly Boston Logan Airport to Philadelphia International Airport, train, taxi

    1. Fly from Boston Logan Airport (BOS) to Philadelphia International Airport (PHL)plane plane BOS - PHL
    2. Take the train from 30th Street Station to Aberdeen Amtrak Stationtrain train
    3. Take the taxi from Aberdeen Amtrak Station to Chestertowntaxi taxi
    5h 17m
    $311–1,080

  6. Fly Boston Logan Airport to Ronald Reagan Washington National Airport, train, drive

    1. Fly from Boston Logan Airport (BOS) to Ronald Reagan Washington National Airport (DCA)plane plane BOS - DCA
    2. Take the train from Washington Union Station to Edgewoodtrain train
    3. Drive from Edgewood to Chestertowncar car
    6h 8m
    $510–1,212

  7. Bus to Manchester Airport, fly to Baltimore-Washington International Airport, bus, taxi

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Baltimore-Washington International Airport (BWI)plane plane MHT - BWI
    3. Take the bus from BWI-Thurgood Marshall Airport to Kent Island, MDbus bus
    4. Take the taxi from Kent Island, MD to Chestertowntaxi taxi
    6h 4m
    $228–807

  8. Train to Theodore Francis Green State Airport, fly to Baltimore-Washington International Airport, bus, taxi

    1. Take the train from South Station to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Baltimore-Washington International Airport (BWI)plane plane PVD - BWI
    3. Take the bus from BWI-Thurgood Marshall Airport to Kent Island, MDbus bus
    4. Take the taxi from Kent Island, MD to Chestertowntaxi taxi
    6h 22m
    $195–581

  9. Train, taxi via New York

    1. Take the train from Boston to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Aberdeen Amtrak Stationtrain train
    3. Take the taxi from Aberdeen Amtrak Station to Chestertowntaxi taxi
    8h 31m
    $209–954

  10. Bus, taxi

    1. Take the bus from Boston to Philadelphia Bus Stationbus bus
    2. Take the bus from Philadelphia Bus Station to Aberdeenbus bus
    3. Take the taxi from Aberdeen to Chestertowntaxi taxi
    12h 20m
    $182–251

Boston Logan Airport (BOS) to Baltimore-Washington International Airport (BWI) flights

Calendar82Weekly Planes
Duration1h 38mAverage Duration
Ticket$61Cheapest Price
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Comparing Your Travel Options

Map of how to get from Boston to Chestertown.ExpandLaunch map view
  • Distance: 432.9 mi
  • Duration: 3h 59m

What companies run services between Boston, MA, USA and Chestertown, MD, USA?

There is no direct connection from Boston to Chestertown. However, you can fly to Baltimore-Washington International Airport (BWI), walk to BWI-Thurgood Marshall Airport, take the bus to Kent Island, MD, then take the taxi to Chestertown. Alternatively, you can take the train to Aberdeen Amtrak Station then take the taxi to Chestertown.

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