Although it’s really a single island, Sugarloaf wraps around, giving the illusion of two islands. Therefore, they have Upper Sugarloaf and Lower Sugarloaf. There are two theories about the name Sugarloaf. One involves an Indian mound on Upper Sugarloaf that is said to resemble an old-fashioned sugarloaf. The other is the fact that a variety of pineapple called sugarloaf was once grown in the area. They’re soft, and don’t travel well, so they’re not used much commercially. The Overseas Highway crosses Upper Sugarloaf around mile markers 19-20.5. It crosses Lower Sugarloaf at about 16.5 -17.5.