Between Bree and the Shire is the Old Forest, mostly unchanged for generations of men and hobbits. Legends have been handed down that the Old Forest is dangerous, that the trees listen and watch and do not like strangers, and that open tracks seem to shift and change. Some hobbits insist that the trees move about and at times surround intruders and hem them in. Old stories declare that in daylight the trees are usually content to watch, except for the more unfriendly ones, but at night in the Old Forest things can be most alarming. Certainly it is a fact that something makes paths. In most of the Old Forest one still sees what Frodo and his friends encountered: tree-trunks of innumerable sizes and shapes, straight or bent, twisted, leaning, squat or slender, smooth or gnarled and branched; and all the stems green or grey with moss and slimy, shaggy fungi.

High Hay

Buckland was originally unprotected from the East, near the Old Forest, until the hobbits built a hedge called the High Hay. Planted generations ago and constantly tended the Hedge is a tall and thick barrier running well over twenty miles from end to end, stretching from the Brandywine Bridge in a big loop to Haysend where the Withywindle flows out of the forest into the Brandywine.

The Hay Gate or North Gate at Buckland is the main way through the Hedge (or the Hay as it is known locally). There is, however, a lesser known route used by the Brandybucks as a private entrance for years, a tunnel made of bricks and large enough for ponies, that dives deep under the Hedge and comes out in the Old Forest. Though not widely advertised, it is used still by those in the know.

Bonfire Glade

On the Hay side of the Old Forest one spot has been called Bonfire Glade since a time long ago when the trees are said to have attacked the Hedge. Meriadoc Brandybuck himself repeated this story of how the Glade got its name: “They do say the trees came and planted themselves right by the Hedge, and leaned over it. But the hobbits came and cut down hundreds of trees, and made a great bonfire in the forest, and burned all the ground in a long strip east of the Hedge. After that the trees gave up the attack, but they became very unfriendly. There is still a wide bare space not far inside where the bonfire was made.” Bonfire Glade remains today a wide circular clearing where no trees grow. Grasses and many tall nettles and thistles abound, as do stalky hemlocks and wood-parsley. The entrance path is not at all easy to find, though whether it moves about or travellers lose their way and become confused is debated.

River Withywindle

The River Withywindle follows a south-west track out of the Downs through the Old Forest until it joins the Brandywine below Haysend. Dark brown waters flow in a lazy winding manner between river banks bordered most of the way by ancient arching willows. The Withywindle valley has a reputation among the hobbits of Buckland as one of the more peculiar spots in the entire Old Forest.

Old Man Willow

Scholars of The Red Book know the reputation of Old Man Willow, singing a sleep spell to the four hobbits. He is described as a huge willow-tree, old and hoary with sprawling branches going up like reaching arms with many long-fingered hands and a knotted and twisted trunk gaping in wide fissures. If he still stands, he is apparently in a deep sleep. No traveller in the Old Forest has reported any encounter for decades, and no living person can be found to identify the exact location of the old tree.

"Tom’s words laid bare the hearts of trees and their thoughts, which were often dark and strange, and filled with a hatred of things that go free upon the earth, gnawing, biting, breaking, hacking, burning: destroyers and usurpers. It was not called the Old forest without reason, for it was indeed ancient, a survivor of vast forgotten woods; and in it there lived yet, ageing no quicker than the hills, the fathers of the fathers of trees, remembering times when they were lords. The countless years had filled them with pride and rooted wisdom, and with malice.”"

- Fellowship of the Ring