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I'm no expert on Cuttyhunk, but I fish the Elizabeth's by boat a ton (including today). A couple of things to consider.
Most of it is shallow, what's not has big rocks that come close to the surface. The south side is particularly tough. Consider heavy mono or Fireline over there. If you use braid, bring an extra spool and plenty of leader material. Expect to lose some needles.
Although you'll find some moving water around the west end, and at times near the clubhouse and north side (and of course around Canapisit) most of the night any pull will be minor.
50/50 chance you'll have some swell/ white water this time of the year.
You'll walk a ton. If you fish from the harbor around the west end and back the south side, you'll cover 3-4 miles of rocky/uneven footing (which will take all night). If you take the road out to the west end and fish back one side or the other, it's more like 1.5 to 2 miles of very difficult going (not counting the walk out). Traveling light and carrying water is important, more so than carrying a big bag of plugs.
If you wade, and you'll want to along the south side as the tide drops, korkers or studded boots are neccessary.
For some years now, we haven't had much big bait in the fall (with the exception of last year when in the very end of October and early November we had a big mass of sea herring settle into the west end of Vineyard Sound which held fish in numbers we don't usually see that late). Juvenile bunker is probably the predominant bait (if you are a match the hatch type).
By far the majority of fish I catch daytime plugging are taken with medium dannys and 2.5 oz pencil poppers. A chrome creek chub popper and spooks also can be good.
By night, (aside from the obvious eel/sluggo option) you can't go wrong with a skin plug (either needle or swimmer). 3-4 needles are worth carrying, and a short shallow runner with some hackle has been good this year. After that you are experimenting. Swimmers work great from the boat, but getting the requisite distance from shore can be a problem. Ditto for bombers, etc. Bottles and darters don't get much use because current isn't real fast and depth is an issue, but you'll probably want to carry one in case. Likewise, I stay away from teasers in the rocks (unless I use a hookless plug which I find hard to stomach), but they do work (my biggest shore bass came from across the way at Gay Head on a Red Gill ahead of a Gibbs needle). The place seems perfect for a big jointed eel if you got one, though I haven't used mine much. I do do pretty well during the day using my own version of the smaller master lure (which is now available from Tatoo), although I can't cast it with the size conventional tackle I choose to use from shore in the rocks.
Bottomline, don't carry too much, go with what you have faith in, and fish with confidence.......even if the place isn't paved with fish, the chance at a real big loner is there with every cast.
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