"Chestertown, MD" Chestertown by frankcanfly

Chestertown Travel Guide: 8 reviews and 45 photos

My favorite of Maryland's Eastern Shore towns, located on the banks of the Chester River, the historic town of Chestertown is the county seat of Kent County.

Once a thriving port of entry for colonial settlers into Maryland, the town has court records dating back to the 1640's. Next to the public dock at the bottom of High Street is the old Customs House, built in the 1740's. Chestertown features many restored 18th century homes, lovely churches, the county courthouse, and several interesting shops. Grand houses built by wealthy merchants line the Chester River.

Chestertown is also home to Washington College. Washington College is the tenth oldest college in the United States. The college was founded in 1782 with the help of George Washington who gave his name and 50 guineas to the college. Washington served as a trustee and received an honorary degree.

I personally know two great professors here!

  • Last visit to Chestertown: Sep 2003
  • Intro Updated May 9, 2016
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Comments (3)

  • kooka3's Profile Photo
    Jul 10, 2008 at 2:13 PM

    interesting pictures . . . can we have some tips to go with them? I'd like to know what you found interesting about the houses you put on here (or perhaps putting them in a general travelogue would be helpful!)

  • spitball's Profile Photo
    Apr 4, 2006 at 3:09 PM

    Chestertown looks like a groovy old place.

  • littlesam1's Profile Photo
    Sep 23, 2003 at 6:21 AM

    I am curious to see what you would include on a Chestertown page. My old supervisor from years ago lives in Chestertown. Maybe her house will be on your page..lol


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