Instead of hiking near the ocean around Dover Island, I decided to hit a couple of small hills on the opposite side of highway 333 and culminate on top of Dover Hill.
Most of the way there you will walk on an un-official trail. It branches out in a couple of places but I chose to always go towards the hill. Before you get to Dover Hill, you will climb another small hill easily recognized by a bolted picnic table. It also offers a couple of good erratic blocs for bouldering. On the way to Dover Hill, you will pass more big erratics begging to be climbed as we'll as other trail branches.
At the top of what you might think is Dover Hill, you will realize it is not it just yet. The next part is for people who either like 1) making it to the official top of the hill and 2) like bushwhacking. Follow my gps track for two ways to get to the top. Both entail some bushwhacking. My 6 year old son was able to do it so I put this as maybe moderate....the bushes are thick but you only need to go for about 100m. The last pitch to the top of Dover Hill offers some 20ft walls so finding a way up is not evident.
Park opposite baseball field once you are in the village of Dover. There is also a pump for firetrucks at the start of the trail
(a) Click Wiki Edit This Page to get placed in edit mode
(b) When finished, your update is available to view as draft (click wiki update pending in trail to see draft)
* note: editors are notified and must approve the change