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How-Boutcha-Love-Me Island is an island that was owned by Mr. Caffrey of Caffrey's Taffy. Caffrey bought the island in an attempt to impress the love of his life, Gwendolyn. He gave the island it's name, imported Highland longhorn cattle from Scotland and named the house, which he built, "The House That Caffrey Built For Gwendolyn." Since Caffrey's death prior to the start of the series, Nathaniel is the only inhabitant of the island along with his gardening tools and the aforementioned cattle. The island also has a boathouse with several boats that belong to Nathaniel.

The island is in fact two separate islands separated by a small channel that can be crossed by a creaky wooden bridge. The cattle reside on the island opposite to where the house and boathouse is, Nathaniel calls it the "wrong side" of the island.

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