The Abenaki Indians named this island Newaggin. European settlers arrived in the 1600s, but the first settler of the island was William Black. He was the son of Black Will, a freed slave that lived in Kittery, Maine. William sold the land his father left him in Kittery and moved to the current Baily Island. The island became known as Will’s Island during his lifetime. In 1742, there is a “first” story told that the Reverend Timothy Bailey bought the island from Will Black for a pound of tobacco. The “second” story is that Mrs. Bailey wanted the island and had her husband bribe local officials to find a “legal flaw” in Will’s land title so that the Baileys could take over the island. There is no certain answer, but when the Bailey’s moved to the island, Will Black, loving the ocean life, moved on to Orr’s Island.
Today, Bailey Island is a popular tourist destination. Pretty coves, gorgeous scenery, delicious food, and island culture draw hundreds of thousands of people to the enjoy the island’s charm every year. Add Bailey Island to your list of Maine places to visit.