I think Aragorn says somewhere he had tentatively planned to go with Frodo and Sam (and Gimli) with Boromir taking Merry and Pippin to Minas Tirith. Not sure about the skate boarding elf. It makes sense to take a dwarf to help getting through the borders (probably by some underground passage---did Aragorn know about Shelob and Co.?).
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The poster formerly known as Tuor of Gondolin.
Walking To Rivendell and beyond 12,555 miles passed Nt./Day 5: Pass the beacon on Nardol, the 'Fire Hill.'
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