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Cuttyhunk is a magical place. Go. Now.
As for the Pier, it was terrific. The dockhand was skilled, helpful and welcoming. I would stay there again, but would also simply pick up a mooring ball.
If you stay on the pier, bring boards to help make the most of your fenders. We had our genders rigged horizontally, which worked fine. Boards would have been better.
Our night at Cuttyhunk was amazing. I cannot wait to go back.
Note: we ended up picking up a mooring on the way back. That was great too.