Approaches
You can approach Cuttyhunk either from the east (Buzzards Bay) or from the west (Rhode Island Sound). In both cases you pass between Cuttyhunk Island and the smaller Penikese Island to the north. The ledges extend three quarters of a mile south and east from Penikese but they are clearly marked and not hard to avoid.
If you're arriving from the south (Vineyard Sound), Quicks Hole is the simplest route through the Elizabeth Islands. Canapitsit Channel - narrow, twisty and ambiguously marked - is right next to Cuttyhunk but used mostly by shoal draft boats with local knowledge.
The entrance to Cuttyhunk Pond is a dredged channel between breakwaters. In 2003 we found a controlling depth of 10 feet at an average low tide. A can marks the southern breakwater, which is frequently awash. The northern breakwater, with its prominent light, is a more certain guide to the channel, though soft shoals do accumulate on its shoulder.
Once inside the Pond, remember that the mooring area is a dredged-out square prone to shoaling at the edges. It is usually marked with small uncharted buoys, but straying much beyond the moorings will land you in shallow water fast.
Anchorages
In fair weather it is possible to anchor in the outer harbor, between Cuttyhunk and Nashawena Island to the east, but it is mostly exposed from northwest to northeast.
Boats frequently anchor inside the pond, at the northern edge of the mooring area. It's tight - with room for only a handful of boats - and the holding is reported to be poor.
Moorings
The town maintains 40 or 50 moorings for visitors inside the pond. The moorings are first-come first-served, and generally fill up on summer weekends, although the pond's flat calm waters do make rafting practical.
The moorings represent an important source of revenue for the town, up to a quarter of the annual budget {BG 9.2.02}. Pick up an empty mooring when you arrive and the harbormasters will come around to collect the fee.
Two private companies, Frog Pond Marine and Jenkins, maintain transient moorings in the outer harbor.
Slips
The slips at the Town Wharf are primarily in shallow water. We've seen a good-sized sailboat tied up at the end of one finger, but for the most part anything with a keel stays on a mooring.
