Approaches
Oak Bluffs harbor is the old landlocked Lake Anthony, connected to Nantucket Sound by a channel first dredged around the beginning of the 20th century. About a mile off the entrance is the Squash Meadow, a shoal marked at both ends; otherwise the entrance is clear. In the prevailing southwesterly, the waters outside Oak Bluffs are comfortably in the lee of East Chop. In a strong north or east wind, however, it's likely to be rough immediately outside the breakwaters.
Water in the entrance channel is an issue for deeper boats. It was last dredged in the early 70s, and in 2004 the controlling depth was reported to be about 6.5 feet at mean low. We've carried 7 feet in and out, but only in the top half of the 1.7 foot tide. As of December 2004, a proposal to dredge the channel to 10 feet awaited approval.
Anchorages
There is no room to anchor inside the breakwater and no protection outside.
Moorings & Slips
Moorings and slips are both handled by the town-owned Oak Bluffs Marina. The 45 moorings are first-come first-served. The 80 slips (mostly tie-ups to the bulkhead running around the harbor perimeter) may be reserved, and generally need to be reserved for summer weekends. Popular weekends can book up before the end of spring. There is a two-night minimum for reservations that include Friday or Saturday.
The small, family-run Dockside Marina just inside the entrance on the left has a handful of slips as well. A member who stayed there on a recent June cruise was impressed by their friendly attitude, and that they answered the phone after 5pm.
We're impressed that the harbormasters have established an 86 decibel noise limit in the harbor, and we've seen them turn boats away whose exhaust was louder.