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

Find Transport to Chestertown

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There are 11 ways to get from Boston to Chestertown by train, taxi, bus, car, ferry, plane, or subway

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, taxi

    best
    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
    $333–477

  2. Drive  376.2 mi

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

  3. Bus, taxi

    1. Take the bus from Boston to New York Midtownbus bus
    2. Take the bus from Midtown - 400 8th Ave to Smyrna, DE - 134 N Dupont Blvdbus bus
    3. Take the taxi from Smyrna, DE - 134 N Dupont Blvd to Chestertowntaxi taxi
    8h 35m
    $184–245

  4. Ferry to Boston Logan Airport, fly to Baltimore-Washington International Airport, bus, taxi

    1. Take the ferry from Long Wharf to Logan Airport Ferry Terminalferry ferry
    2. Fly from Boston Logan Airport (BOS) to Baltimore-Washington International Airport (BWI)plane plane BOS - BWI
    3. Take the bus from Baltimore to Kent Islandbus bus
    4. Take the taxi from Kent Island to Chestertowntaxi taxi
    5h 35m
    $284–1,155

  5. 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
    $259–994

  6. 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
    $96–174

  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 Baltimore to Kent Islandbus bus
    4. Take the taxi from Kent Island to Chestertowntaxi taxi
    6h 4m
    $199–598

  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 Baltimore to Kent Islandbus bus
    4. Take the taxi from Kent Island to Chestertowntaxi taxi
    6h 32m
    $210–661

  9. Ferry to Boston Logan Airport, fly to Philadelphia International Airport, train, taxi

    1. Take the ferry from Long Wharf to Logan Airport Ferry Terminalferry ferry
    2. Fly from Boston Logan Airport (BOS) to Philadelphia International Airport (PHL)plane plane BOS - PHL
    3. Take the train from 30th Street Station to Aberdeen Amtrak Stationtrain train
    4. Take the taxi from Aberdeen Amtrak Station to Chestertowntaxi taxi
    7h 2m
    $331–1,169

  10. Ferry to Boston Logan Airport, fly to Ronald Reagan Washington National Airport, train, drive

    1. Take the ferry from Long Wharf to Logan Airport Ferry Terminalferry ferry
    2. Fly from Boston Logan Airport (BOS) to Ronald Reagan Washington National Airport (DCA)plane plane BOS - DCA
    3. Take the train from Washington Union Station to Edgewoodtrain train
    4. Drive from Edgewood to Chestertowncar car
    7h 54m
    $472–1,148

  11. Ferry to Boston Logan Airport, fly to Washington Dulles International Airport, subway, train, drive

    1. Take the ferry from Long Wharf to Logan Airport Ferry Terminalferry ferry
    2. Fly from Boston Logan Airport (BOS) to Washington Dulles International Airport (IAD)plane plane BOS - IAD
    3. Take the subway from Washington Dulles International Airport, Silver Line Center Platform to Metro Center, Blue/Orange/Silver Line Center Platformsubway subway
    4. Take the train from Washington Union Station to Edgewoodtrain train
    5. Drive from Edgewood to Chestertowncar car
    8h 31m
    $622–1,147

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

Calendar110Weekly Planes
Duration1h 38mAverage Duration
Ticket$70Cheapest Price
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Comparing Your Travel Options

Map of how to get from Boston to Chestertown.ExpandLaunch map view
  • Distance: 443 mi
  • Duration: 8h 21m

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

There is no direct connection from Boston to Chestertown. However, you can take the train to Aberdeen Amtrak Station then take the taxi to Chestertown. Alternatively, you can take the bus to New York Midtown, walk to Midtown - 400 8th Ave, take the bus to Smyrna, DE - 134 N Dupont Blvd, then take the taxi to Chestertown.

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