It says in UT that one reason the rangers could not hold out against the Black Riders at Sarn Ford was because their captain (Aragorn) was away north, watching the East Road. It doesn't say whether he knew to expect the hobbits to come through there or not, or whether it was coincidence. His behavior in Bree seems to indicate that he knew they would be travelling at that time of year. If Bombadil had messages from Gildor, is it possible that the Rangers did as well?
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Yet all the while I sit and think of times there were before,
I listen for returning feet and voices at the door.
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