Those of you who have been reading Arwen’s Journey will probably have noticed a chapter in which King Elessar is responding to one of many letters he has received from Frodo Baggins, now a resident of Valinor. A later chapter features a conversation between the King and Samwise Gamgee in which the Hobbit hero alludes to letters he has been exchanging with Frodo. Some readers might consider this a violation of Middle Earth canon, although I think that there may be some leeway for inventiveness in this area.
I know many will insist that The Straight Path to Valinor was only supposed to be one way, but there's a practical reason why I disagree with this premise. By the end of the Second Age, the virgin forests east of the Misty Mts. and south of the White Mts. had been logged off, leaving nothing but scattered, second growth woodlands. The primeval density of the forests never returned, I would assume, due to later harvesting of trees for fuel, pulp and lumber. If the Elves built new ships every time several hundred of them left the Grey Havens, all of Lindon and Eriador would have been denuded of useful trees long before the Third Age began.
Even in a generously wooded parcel of mixed hardwoods, it would take the mature oak trees from 10-20 acres to build just one ship the size of the one shown at the end of The Return of the King. The people of those regions would also have been consuming an enormous amount of wood for domestic use: cooking, heating and charcoal production. It's highly unlikely that the forests would have had time to regenerate quickly enough to keep up with the further demands of shipbuilding. I've harvested firewood and engaged in forest management for over 40 years, so I have a lot of practical knowledge on this subject.
With all due respect to Tolkien, I seriously doubt that he did any practical research in forestry, not to mention the logistics involved in transporting lumber over longer and longer distances as the nearby woods were exhausted. There had to be another, more practical solution: namely, that there was a fleet of Elven ships operating between Mithlond and the east coast of the Undying Lands. I think even Círdan the Shipwright would agree with me on this one.
Along with a fleet transporting Elves across the aetherous ocean, you would most likely have some form of trade going on too, and surely some form of mail service. I mean, it seems unlikely that two lifelong friends like Frodo and Sam wouldn’t want to continue their friendship via correspondence after Frodo sailed to the Undying Lands. I also think that Galadriel would want to keep in touch with Celeborn from time to time, just to hear the latest news and gossip from East Lorien.
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Letters from the Undying Lands by Karlmir Stonewain