First of all it should be noted that the extent of the Lone-lands is debated. Probably the name once was synonymous with Eriador. However, today we know the Lone-lands as Hobbits and Bree-men knew it: the wilderness east of Bree, something inconvenient that lines the Great East Road. This section discusses the more narrow scope.
While the Lone-lands as such is little told of in Tolkien's works (it was not mentioned at all until later editions of The Hobbit and not at all in The Lord of the Rings) three of its locations are mentioned: the Forsaken Inn, Weathertop, and the Last Bridge. The history of Weathertop reveals much about the history of the Lone-lands: Elendil built the "Tower of Amon Sûl" in II 3320, when the North-kingdom of Arnor was young. It housed the chief palantír that was used to communicate across the vast kingdom. In III 861, when Arnor broke apart, Arthedain claimed possession of the Tower and the palantír, but from then on the three Arnorian parts disagreed on its future. Facing many threats, Weathertop was overthrown by Angmar in III 1409 and was destroyed and burnt to ashes; however, the witch-king failed to lay hands on the palantír (though it was later lost at sea).
The Great East Road runs through the Lone-lands like an artery, and it has served more than one ancient kingdom as highway and borderline. Thousands of years ago, it connected the Dúnedain kingdom of Arnor –sister kingdom of Gondor– to Rivendell, the Misty Mountains, and lands east. Throughout its lifetime, its travellers have added wealth to residents along the Road who provided services of all sorts.
Ref: Originally from http://www.lotro.com/gameinfo/heros-guides/336-feature-article-heros-guide-to-the-lone-lands, but also captured at legacy.zam.com
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