The village of Bree was guarded from outsiders by a deep ditch and a hedge. The great East Road passed through this hedge on its western side, and exited again in the southern corner where the hedge and dike met the sides of the Bree-hill. At each of these points stood a gate, that was closed and guarded after nightfall. The gate that looked towards the Shire, the West-gate, was guarded by one Harry Goatleaf during the War of the Ring, though he later joined with Bill Ferny and the followers of Saruman.
Bree itself is first definitively mentioned in about III 1300, but it seems to predate this by some time. It's less clear whether the town's defences and gates were in place from this early point in history, or were added later. The year III 1300 is also associated with the foundation of Angmar and a growth in the Shadow, so it seems reasonable to assume that Bree would have had defences in place even at this early date.
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