The Island of Islesboro

Islesboro is a long, narrow island in Penobscot Bay directly across from the town of Lincolnville. The location of the famous summer colony and yachting center of Dark Harbor, the island hosts a year-round population of lobstermen, carpenters, caretakers, and other professionals.

Penobscot Indians called Islesboro Pitaubegwimenahanuk, meaning “the island that lies between two channels.” Situated in upper Penobscot Bay, the narrow, 14-mile island is the marker between East and West Penobscot Bay. It was part of the Waldo Patent. First called Long Island Plantation, and was settled in 1769. It would be incorporated as Islesborough on January 28, 1789, although over time the spelling was contracted to Islesboro.

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 Gilded Age resort community, and many large summer homes were built by the wealthy. Their large yachts cruised and raced throughout the Gulf of Maine. The town remains a seasonal enclave to many notable residents.

What to see?

  • Sailors’ Memorial Museum, located in the former keepers’ house at Grindle Point Lighthouse.
  • Grindle Point Lighthouse
  • Sprague’s Beach located near Turtle Head
  • Warren Island State Park

For more information please visit the Island Institute page on Islesboro
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