Paths within the Old Forest were not necessarily permanent, and the strange trees of that forest could evidently rearrange such things from time to time. So, it is not necessarily the case that the Withy-path would have remained in place from year to year, or even from day to day.

Nonetheless, despite the strangeness of the wood, it does seem that the path down the Withywindle held a relatively stable course. Frodo and his companions met Tom Bombadil on the path in autumn, but he clearly expected to be able to travel that way the following spring, and the poem "The Adventures of Tom Bombadil" also describes Tom travelling down Withywindle some years beforehand. These facts seem to point to the Withy-path being at least several years old, and possibly much older. This relative permanence might in turn hint that Tom's influence held the trees back from the path, or might be simply due to the fact that the path ran along the bank of a river, and was therefore harder for the trees to affect.

Withy is an old name for the willow tree, so the name 'Withy-path' literally means 'willow-path'. The path did indeed run beneath riverside willows, notably Old Man Willow, and the meaning may be as simple as this. However, it was also the path along the river Withywindle, so the name might equally represent an abbreviated form of 'Withywindle-path'.

We know that the Withywindle ran southwestwards along its lower course, but beyond this we have little detail about the river. Deeper into the Old Forest, the river and path were said to have run from the east (and indeed this must be the case for the river to fit the known geography), but we have no maps to show exactly where or how the river turned.

The Withy-path followed the banks of the Withywindle, so its course is equally uncertain. We can be sure that it ran along the western and northern banks (because otherwise Frodo and his companions would have needed to cross the river to use it) but beyond this, the details of the path are necessarily speculative.