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The Trollshaws were located between the River Hoarwell and the River Bruinen north of the Great East Road. The Last Bridge spanned the Hoarwell west of the Trollshaws, and Rivendell was across the Bruinen east of the woods. North of the Trollshaws were the Ettenmoors, or Troll-fells - a high, barren land inhabited by Trolls. The Trollshaws stretched over 50 miles from east to west. Many of the trees were pines, though there were some beech trees as well. The land where the woods grew was hilly. The hills became higher deep in the forest, and narrow ravines wound among them.

There was at least one path in the forest made by Trolls, but for the most part there was no easy way through the Trollshaws. The ground was littered with stones and fallen trees. The ravines ran in different directions and some had dead ends and steep cliffs on either side. In some of the hills there were shallow caves, and on top of some of the hills there were castles and towers that had been built by the Men of Rhudaur.

Rhudaur was one of the three Kingdoms of the Dunedain that resulted from the division of the North-kingdom in 861 of the Third Age. Rhudaur was the easternmost Kingdom and it included the Trollshaws. The Dunedain of Rhudaur diminished and control was seized by a lord of the Hill-men who was secretly allied with the Witch-king of Angmar. In 1409, the remaining Dunedain were slain or driven out. Rhudaur fell completely under the control of the Witch-king, and the Men who lived there were evil.

When the Witch-king was defeated in 1975, the Men of Rhudaur were completely destroyed. The area, including the Trollshaws, became largely uninhabited. The fortifications in the forest fell into ruin. Trolls came down from the Ettenmoors and roamed the forest, preying on travellers on the Great East Road.