[2] It has a summer colony accessible by state ferry service from Lincolnville Beach three miles to the west, by private boat, or by air taxi service.

Home to Warren Island State Park, Islesboro includes the village of Dark Harbor.

The Penobscot people called it Pitaubegwimenahanuk, meaning "the island that lies between two channels", although André Thevet recorded the name Aiayascon in 1556.

It was incorporated as Islesborough on January 28, 1789, although over time the spelling was contracted to Islesboro.

[4] With many harbors and coves, the island was home to the largest commercial shipping fleet in the bay during the 19th century.

Following the Civil War, however, Islesboro developed as a resort community, and many large and luxurious summer homes were built.

Islesboro Island is narrow, mainly north-south and 14 miles long.

Of all households 34.4% were made up of individuals, and 15.2% had someone living alone who was 65 years of age or older.

Of all households 30.7% were made up of individuals, and 13.6% had someone living alone who was 65 years of age or older.

It is also unique that it allows mainland students to pay tuition to attend from grades 5 through 12.

The competitive sports offered through the school include cross country running, sailing, soccer, basketball, and Ultimate Frisbee.