The breakwater is sus during winter. I went on Christmas day and thought better than to go out. One slip, and you're a gonner. But maybe at low tide on one of these 50 degree days we have been having? It's probably better to just trek over to Owls Head if you feel like driving.

Maiden cliff should be fine. Wear spikes, take trekking poles, and stay away from the cliff itself. We don't need a reason for a second cross up there. Also, I would turn around and come back at the cliff instead of continuing on. It turns into a bit of a scramble afterward. However, Mount Meginticook trail from the state park is safe all the way up (with spikes, at least).