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Be aware that these moorings are in the outer harbor, not inside the Cuttyhunk pond, close to town!
Inside moorings are managed by the town of Gosnold and they are NOT in Dockwa! They are in a first come, first serve basis, but there are plenty! Unless you are coming during a major holiday, there should be no problem in getting one.
In the rare situation that you cannot get a morning inside the pond, you can easily anchor outside, where these outer moorings are; I don't see any reason to pay for them. Don't waste your money!