I myself did not necessarily interpret Gandalf's report of the Rangers visiting Deadmen's Dike as anything having to do with sweet memories. To me it seemed to be another part of their regular tour for the purposes of protecting Eriador. Admittedly probably not as sinister as Barliman's idea of it, which is presumably an old wife's tale, but perhaps as dangerous as other regions.
In the end, you have to go with the reports of where the Rangers were found. Somewhere close to Rivendell, one assumes, since Halbarad got the message that Aragorn needed help. Their presence close to Weathertop is also noted, since they left the firewood that the Aragorn and the hobbits found. And down near Tharbad, since they were driven off by the Nazgul. Bombadil certainly knows about them, since he talks of the
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forgotten kings walking in loneliness, guarding from evil things folk that are heedless
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Given their mission, one assumes that where they are found is somewhere close to where the evil things, whatever they are, would invade...