What's now the border between Orleans and Eastham was once a somewhat shallow continuous passage between Cape Cod Bay and the open Atlantic Ocean. The 'river' that ends at Boat Meadow Beach, in Eastham, once wound it's way east, through what's now the Eastham rotary, to Town Cove. Records show that it was used by British government frigates in 1717 in an attempt by the governor to recover the booty from the pirate ship Whydah after it sank off the outer beach. During the war of 1812 it was used by salt carrying boats to evade the British blockage around Provincetown.
The canal was always a shallow affair, and it's Bayside entrance on the sand flats made it undependable, even at high tide, thus eliminating it from the list of passages when the current Cape Cod Canal was being engineered.
There's been a fair amount written about Jeremiah's Gutter, including a short piece in Henry David Thoreau's book, Cape Cod, written in 1865. My research came, mostly from the book It Happened on Cape Cod By Shawnie M. Kelley (2006).
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