This photograph, taken from the air, shows the situation of the second Islesboro Inn (1917) overlooking Penobscot Bay to the east. The original Islesboro Inn burned in 1915. The Philler Cottage across the street can also be seen, as well as a corner of the Dark Harbor Pool.

The Islesboro Inn was built in the southern section of Islesboro, called Dark Harbor, to attract wealthy families, who would buy lots and build summer "cottages."