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Circa 1906. "Harbor from Crocker Park, Marblehead, Massachusetts." 8x10 inch dry plate glass negative, Detroit Publishing Company. View full size.
looks to me rather like a Chesapeake pungy. The crazy long counter and almost-as-long bowsprit, combined with fore-and-aft rigging, suggest a Chesapeake Bay origin.
What a delightfully dense-packed bunch of sloop-boats, schooners, and two steam launches (or maybe naphtha? in the center left background). Almost everything is gaff-rigged unless it has power or is a dory propelled by oars. It takes real seamanship to anchor so close together without having accidents! Especially when most of the vessels are engineless sailboats.
In the left background is a large black (dark colored, anyway) schooner with exceptionally long stern overhang but very short masts. I looked in vain for a funnel, so I don't think it's a steam yacht. Wonder what the story is behind it.
The men who rowed George Washington across the Delaware river on Dec. 25-26 1776 were all from Marblehead.
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