The fact that the Road led to the Ford of Bruinen strongly suggests that it was made after the founding of Rivendell in the mid-Second Age. Its most likely construction date would be after the foundation of Arnor at the end of the Second Age.

We have textual evidence that the Old Road reached as far as the Grey Havens at its western end, but its precise route westward of the Shire is not shown on any map. This is the reason that the western part of the road is shown as a dashed line on this map. The road may have diverged from the line shown here (though presumably not by a great deal, since this is the direct route to the Grey Havens). This stretch of the Old Road was likely connected somehow to the Tower Hills, which lay close to its route, and were an important site to both the Men of Arnor and Elves of Lindon.