"At first they had passed through hobbit
-lands, a wide respectable country inhabited by decent folk, with good roads, an inn or two, and now and then a dwarf
or a farmer ambling by on business."
The Hobbit 2
Those lands owned or cultivated by the Hobbits, or at least familiar to them. The Hobbit-lands certainly contained the Shire and Buckland, and perhaps stretched beyond their borders. When Bilbo and the Dwarves passed out of the Hobbit-lands, they came to an unspecified place where the people used strange speech, and sang unfamiliar songs. This may be an oblique reference to the Bree-land, and if so it places Bree outside the Hobbit-lands as such, despite the fact that Hobbits lived among the Men of Bree.
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