Brooksville is on the point of land located just across the harbor from Castine, and islands, such as Ram Island (located between Castine and Cape Rosier) would have been easily accessible by boat from Castine.
Indian Bar, on Cape Rosier, was one the routes of the Wabenaki Indians from the Penobscot River to Mount Desert, Deer Isle, or the islands of Penobscot Bay. The Indian Bar provided a short portage into Smith Cove, crossing Cape Rosier to Horseshoe Cove, and from thence to Eggemoggin Reach, from whence one could follow one route to Benjamin River and Salt Pond to Bluehill Harbor, another to Naskeag and Mount Desert, a third to Deer Isle and the outer islands of Penobscot Bay, and a fourth from Billings Cove and Walkers Pond to the Bagaduce River. Coming full circle, one crossed from the Bagaduce to Hatch's or Poverty Cove, above Castine village, to Wadsworth's Cove, and from thence north along the Penobscot. Wadsworth's Cove was the beginning or ending of the Minnewo'kun, "the many directions route."
There isn't much history to relate about Ram Island, other than, as its name suggests, it was used as a sheep pasture, perhaps in connection with the farm at Holbrook Island. Holbrook, or Smart's Island, was occupied prior to the Revolution, and was purchased by Smart's brother-in-law, John Bakeman, and was thus known as Bakeman's Island in 1779. John Bakeman, a shipbuilder and sawmill owner at Goose Falls, Cape Rosier, sold the island to Capt. Jesse Holbrook for £150 in 1783. Capt. Jesse Holbrook died on the island on September 20, 1791 and is buried there with some of his children.
Capt. Jonathan Holbrook, Capt. Jesse's son, sold the island to Capt. Elisha Dyer of Castine in 1801 and removed his family to Northport. The extended Holbrook family would include shipbuilders at Penobscot, Castine, and Islesboro, a fraternity of shipwrights and a pattern of craftsmanship that would define shipbuilding in Hancock County in the nineteenth century. Capt. Holbrook lost his schooner "President," built at Islesboro by his brother-in-law Mighill Parker 1796, to French privateers in the West Indies in 1797, and the schooner "Active" to French privateers, who were interned captured by English privateers in 1800. Benjamin Hook Senior and Abraham Moor, farmers, were living together in an extended household, in 1850, on Holbrook Island, which included Robert Bowden, a mariner. Moor, according to oral history, was expelled from Yale, and spent the remainder of his life as a local eccentric. The Neymans, who also lived on the island, are alleged to be the children of Hook's inamorata Mrs. Ryder.
– Mark Honey