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Cuttyhunk is our happy place. We normally anchor outside and avoid the pond - especially in higher winds. The moorings are tight and many boaters do not do so well picking up those unusual moorings. We will only go inside if the wind is Northy.
The outside anchorage is huge with great holding and great depths. There are also moorings out there (different provider) if you prefer. The raw bar boat serves the outer harbor too.
The moorings are famously (or infamously) odd with a vertical pole and loop that you put dock lines through. For most sailboats (and many power boats), the pole is at a height where your lines will get chaffed on your anchor all night. For that reason, many people (including us) dangle their anchors in the water between the mooring bridals.
It's a great place to get the water toys/kayaks/sups out and explore. Fantastic swimming area in the outer harbor too. You can anchor your dinghy in the pond channel and swim and gawk at the passing boats. It never gets old.