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

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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
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Aberdeen Amtrak Stationtrain
    3. Take the taxi from Aberdeen Amtrak Station to Chestertowntaxi
    5h 59m
    $173–481

  2. Drive 237.6 mi

    cheapest
    1. Drive from Poughkeepsie to Chestertowncar237.6 mi
    4h 43m
    $44–63

  3. Train, bus, taxi

    1. Take the train from Poughkeepsie to Grand Central Terminaltrain
    2. Take the bus from Port Authority Bus Terminal to Aberdeenbus
    3. Take the taxi from Aberdeen to Chestertowntaxi
    9h 12m
    $175–254

  4. Train, fly, bus, taxi

    1. Take the train from Poughkeepsie Amtrak Station to Albany-Rensselaer Amtrak Stationtrain
    2. Fly from Albany County Airport (ALB) to Baltimore-Washington International Airport (BWI)planeALB - BWI
    3. Take the bus from BWI-Thurgood Marshall Airport to Kent Island, MDbus
    4. Take the taxi from Kent Island, MD to Chestertowntaxi
    7h 30m
    $378–1,021

  5. Bus, drive

    1. Take the bus from Rosendale to New Yorkbus
    2. Take the bus from Port Authority Bus Terminal to White Marsh Park & Ridebus
    3. Drive from White Marsh Park & Ride to Chestertowncar
    9h 21m
    $65–151

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

Calendar41Weekly Planes
Duration1h 24mAverage Duration
Ticket$63Cheapest 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 the train to Grand Central Terminal, walk to E 42 St/Madison Av, take the bus to West 42nd Street & 8th Avenue, walk to Port Authority Bus Terminal, take the bus to Aberdeen, then take the taxi to Chestertown.

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