First, the Hobbits leave Hobbiton. Then they cross the Ferry from the Four Farthings into Buckland. Then they leave the Shire through a gate in the wall, and wander for a time in an Old Forest and across the downs. Finally, they enter the world of Men through another gate in a wall, and Tolkien repeats his familiar plan of attack.

In a quasi-historical manner quite similar to what he used when the Hobbits were crossing into Buckland, Tolkien gives us a brief description of Bree and its origins, and then (widening his scope) a brief account of its socially mediatory status between the Shire and the rest of the world. The most important difference between the history of Buckland and the history of Bree is that Bree goes back quite a bit further—the Breelanders consider themselves “descendants of the first Men that ever wandered into the West of the middle-world.” In homely Bree, home of the Prancing Pony, we already encounter the flavor of something mythic.

As befits this stage of the journey, however, Tolkien paints Bree in a curious blend of the mythic, the homely, the familiar, and the strange. He does this by adopting for a moment the different perspectives of the Hobbits themselves. To Samwise son of Hamfast (Anglo-Saxon for “Home-bound” or “Home-body”), the houses of Men and the Inn at Bree appear unwelcoming, the likely hide-outs of Black Riders, and generally much too tall. Frodo, however, shares none of Sam’s perceptions and expects the Inn to be “homelike enough inside.” And, indeed, the inside is very Shire-like, complete with round windows and the hallmark of a Hobbit’s being at home—a good supper.

As a first encounter with the world of Men, therefore, Bree is just unfamiliar enough to put the Hobbits well on their guard, and familiar enough to gradually lull them off it.