Bailey Island

The island was settled in approximately 1720 by Will Black, an African man and perhaps the best known frontiersman in the eastern part of the United States.

Horse / Harbor Island

Purchased on July 6, 1794 by Benjamin Darling, a freed or possibly escaped African who was known as a “sturdy and industrious individual.” Although it is not clear how Darling arrived in the area, it is widely accepted that either his mother smuggled him out of slavery or that having saved the life of his enslaver during a shipwreck, he may have been granted his freedom. Darling, his white wife, Sarah Proverbs and their sons Isaac and Benjamin Jr. were the first inhabitants of the island. The family owned the property until 1847 when they sold it to Joseph Perry and then moved to Malaga Island.

Malaga Island

A maroon society, initially inhabited by Benjamin Darling and other Africans who had fled slavery. These early settlers maintained their ancestral languages and lived in caves to avoid detection. Established in 1847, Malaga Island was typical of many island communities of the eastern Casco Bay which were seldom occupied by “legal” owners. Fishermen would store their gear in crudely constructed sheds or shacks and often remain on the islands as unchallenged “squatters” for generations. Having little contact with the mainland, these individuals were not counted in the census, seldom paid taxes, and rarely voted. Illness and even death were taken care of at home, as was education. Most of the inhabitants of Malaga Island were direct descendants of Darling including his sons Isaac and Benjamin, both of whom married women of the island and raised a total of fourteen children. Over time other groups also inhabited the island including Irish, Scottish, and Portuguese.

Families inter-married and worked together for the mutual benefit of the struggling community. However, as the island became a more desirable “vacation” destination, there was increasing pressure to remove the inhabitants who had become an embarrassing “eyesore” to “respectable” members of the mainland community. Skillfully utilizing the press to denigrate the colony with newspaper headlines such as this one from the Casco Bay Breeze August 24, 1905, “Malaga, the Home of Southern Negro Blood…Incongruous Scenes on a Spot of Natural Beauty in Casco Bay”, the stage was set for the illegal and inhumane eradication of the islanders. In 1912, the Malagaites, who had been wrongly characterized as an incompetent, lazy and mentally ill lot, were served with a writ to vacate the island. With no more than the signature of a mainland doctor, families were sent to the Maine School for the Feeble-Minded in order to remove them from public view. The state then destroyed all the houses and shelters on the island, exhumed the graves of family members and destroyed all evidence that they existed.

A January 1913 newspaper headline read, “Cleaning up Malaga Island, No longer a Reproach to the Good Name of the State” and noted “Not only have the inhabitants of the island been raised to a standard of living they probably never dreamed of before and all done for them that is possible under the conditions, but the state has saved a nice little bundle of coin as well.” Today, the only remaining monument to those former Malagaites is a row of white markers on a grassy hill near Pineland Center.


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