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

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There are 9 ways to get from Brattleboro to Chestertown by train, bus, taxi, car, or plane

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, bus, taxi

    best
    1. Take the train from Brattleboro Station to Ny Moynihan Train Hall At Penn Stationtrain train
    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
    9h 24m
    $214–324

  2. Drive 361.7 mi

    cheapest
    1. Drive from Brattleboro to Chestertowncar car 361.7 mi
    6h 54m
    $66–96

  3. Bus, drive

    1. Take the bus from Brattleboro to Hartford Union Stationbus bus
    2. Take the bus from Hartford to New Yorkbus bus
    3. Take the bus from New York to Baltimorebus bus
    4. Drive from Baltimore to Chestertowncar car
    11h 12m
    $133–197

  4. Train to Bradley International Airport, fly to Baltimore-Washington International Airport, bus, taxi

    1. Take the train from Brattleboro Station to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Baltimore-Washington International Airport (BWI)plane plane BDL - 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
    7h 22m
    $220–612

  5. Train, taxi

    1. Take the train from Brattleboro Station 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
    9h 39m
    $234–379

  6. Train to Bradley International Airport, fly to Ronald Reagan Washington National Airport, train, drive

    1. Take the train from Brattleboro Station to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Ronald Reagan Washington National Airport (DCA)plane plane BDL - DCA
    3. Take the train from Washington Union Station to Edgewoodtrain train
    4. Drive from Edgewood to Chestertowncar car
    9h 26m
    $113–540

  7. Train to Bradley International Airport, fly to Philadelphia International Airport, train, taxi

    1. Take the train from Brattleboro Station to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Philadelphia International Airport (PHL)plane plane BDL - 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
    8h 46m
    $223–640

  8. Train, bus to Albany County Airport, fly to Baltimore-Washington International Airport, bus, taxi

    1. Take the train from Brattleboro Station to Northamptontrain train
    2. Take the bus from Northampton to Albany Bus Terminal, NYbus bus
    3. Fly from Albany County Airport (ALB) to Baltimore-Washington International Airport (BWI)plane plane ALB - BWI
    4. Take the bus from BWI-Thurgood Marshall Airport to Kent Island, MDbus bus
    5. Take the taxi from Kent Island, MD to Chestertowntaxi taxi
    9h 28m
    $255–792

  9. Train, train to Boston Logan Airport, fly to Baltimore-Washington International Airport, bus, taxi

    1. Take the train from Brattleboro Station to Springfieldtrain train
    2. Take the train from Springfield to Bostontrain train
    3. Fly from Boston Logan Airport (BOS) to Baltimore-Washington International Airport (BWI)plane plane BOS - BWI
    4. Take the bus from BWI-Thurgood Marshall Airport to Kent Island, MDbus bus
    5. Take the taxi from Kent Island, MD to Chestertowntaxi taxi
    10h 27m
    $342–1,271

Bradley International Airport (BDL) to Baltimore-Washington International Airport (BWI) flights

Calendar28Weekly Planes
Duration1h 22mAverage Duration
Ticket$58Cheapest Price
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Questions & Answers

Map of how to get from Brattleboro to Chestertown.ExpandLaunch map view
  • Distance: 424.4 mi
  • Duration: 9h 24m

What companies run services between Brattleboro, VT, USA and Chestertown, MD, USA?

There is no direct connection from Brattleboro to Chestertown. However, you can take the train to Ny Moynihan Train Hall At Penn Station, walk to Midtown - 400 8th Ave, take the bus to Smyrna, DE - 134 N Dupont Blvd, then take the taxi to Chestertown. Alternatively, you can take a bus from Brattleboro to Chestertown via Hartford, New York, and Baltimore in around 11h 12m.

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