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October 14, 2026

ARCHIVE Chestertown Spy

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9 Brevities

Chestertown Flashback: Massey, Maryland

September 5, 2025 by Historical Society of Kent County

Image courtesy of Historical Society of Kent County.

This undated photo of downtown Massey, Maryland from the turn of the 20th century reveals a peaceful downtown with early automobiles on a still-unpaved central thoroughfare, towering trees, and classic Eastern Shore woodframe buildings.

Zoom in to find details that are hard to discern, like two white-clad figures standing in front of the post office. Another, in the center of the frame but almost undetectable and even more ghostly, is standing in or perhaps crossing the street. This form, possibly a young boy caught in motion and blurred in the long exposure needed for photographs of the era, manages to bring the image to life more acutely despite being so hard to make out, perhaps because he is so clearly an unposed and unintended subject.

Share your memories of Massey in the comments below or by emailing director@kentcountyhistory.org.

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Filed Under: 9 Brevities

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Letters to Editor

  1. Juanita says

    September 5, 2025 at 3:18 PM

    This appears to be after a severe weather event judging from the leaning trees and the flooded road. There appears to be a telegraph or electric pole next to the trees that are leaning, but no downed wire. It would be interesting if someone could date the photo.

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