Brooksville was explored first by James Rosier in 1605, where he discovered the “canoe men”, also known as the Penobscot peoples.  It was first settled in 1777.  Most of the town was part of David Marsh’s Township #4, which included Brooklin and Sedgwick.  In the early days, Brooksville had 5 distinct villages.  Parts of Brooksville, Castine and Penobscot were combined in 1787 to form one town called Penobscot, with the business center in Castine.  In 1817 Brooksville’s separated parts were joined back together and the town incorporated as Brooksville, named after Governor Brooks.