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

Find Transport to Chestertown

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There are 5 ways to get from Poughkeepsie to Chestertown by train, taxi, bus, 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, taxi

    best
    1. Take the train from Poughkeepsie Amtrak 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
    6h
    $181–290

  2. Drive 237.6 mi

    cheapest
    1. Drive from Poughkeepsie to Chestertowncar car 237.6 mi
    4h 44m
    $44–63

  3. Bus, drive

    1. Take the bus from Newburgh ShortLine Transportation Center to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to White Marsh Park & Ridebus bus
    3. Drive from White Marsh Park & Ride to Chestertowncar car
    9h 16m
    $80–195

  4. Train, fly, bus, taxi

    1. Take the train from Poughkeepsie Amtrak Station to Albany-Rensselaer Amtrak Stationtrain train
    2. Fly from Albany County Airport (ALB) to Baltimore-Washington International Airport (BWI)plane plane ALB - 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 30m
    $229–773

  5. Train, bus, taxi

    1. Take the train from Poughkeepsie to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Philadelphia Bus Stationbus bus
    3. Take the bus from Philadelphia Bus Station to Aberdeenbus bus
    4. Take the taxi from Aberdeen to Chestertowntaxi taxi
    9h 55m
    $174–252

Albany County Airport (ALB) to Baltimore-Washington International Airport (BWI) flights

Calendar38Weekly Planes
Duration1h 22mAverage Duration
Ticket$72Cheapest Price
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Questions & Answers

What companies run services between Poughkeepsie, NY, USA and Chestertown, MD, USA?

There is no direct connection from Poughkeepsie to Chestertown. However, you can take the train to Ny Moynihan Train Hall At Penn Station, take the train to Aberdeen Amtrak Station, then take the taxi to Chestertown. Alternatively, you can take a train from Poughkeepsie to Chestertown via Beacon, Beacon Station, Newburgh ShortLine Transportation Center, Port Authority Bus Terminal, and White Marsh Park & Ride in around 9h 16m.

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