According to comments reproduced in Unfinished Tales, at the end of the Second Age the road that ran down from the High Pass led to a bridge across Anduin. Indeed, at the time of the War of the Last Alliance the bridge was strengthened to accommodate the southward-marching armies of Elves and Men. This crossing point is the location later occupied by the Old Ford, so at some point during the Third Age the bridge must have been broken.
Given that the crossing was known as the Old Ford at the end of the Third Age, this was presumably some time beforehand, though we have no specific date. We know that the bridge of Tharbad was ruined in the widespread flooding the followed the Fell Winter in III 2912, and perhaps the same is true of the lost bridge that once spanned Anduin. If so, the Old Ford would have been a little more than a hundred years old by the time of the War of the Ring.
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