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There’s no answer to the “Did Thranduil sail?” question and we’re never going to get one and maybe sometimes that drives me up the wall, like, if I could take a quick jaunt over to the afterlife and ask Tolkien some questions about his world, there are far better questions! Far more complex and central to the themes questions! And yet invariably, my first thought is always, “So, tell me Thranduil eventually sailed, right?” Sigh.
But I really do think that he sailed and I’ve talked about it a few times before and I was reading over the post-LOTR stuff in the appendices again and was struck by:
Which I’ve read a bunch of times before, of course. But for reference, the map of Mirkwood (while it was still Mirkwood):
What happened was: During the War of the Ring (the battle with the Fellowship and the One Ring, where Sauron was finally defeated once and for all), there was shit going down in Mirkwood (the Battle Under the Trees) and it was a hard fight, but Thranduil eventually won his battle against Sauron’s forces.
Afterwards, Sauron and the Nazgul are gone from the forest. Most of the really poisonous evil is gone or leaving from the world (including the forest). There are probably lingering pockets or Orcs or spiders or other nasties here and there, for the most part, that forest would be recovering and safe again!
So, on the Elven New Year, Celeborn and Thranduil meet up and they divide that great big forest into thirds. The bottom third (where Dol Guldur used to be) is taken by Celeborn and becomes East Lorien. The middle part (from East Bight to the mountains) is given to the Beornings. The northern part (from the mountains northward) was kept by Thranduil and renamed Eryn Lasgalen (Wood of the Green Leaves).
Now, when Oropher came to Greenwood originally, the settled in the south, their capital used to be right there around Dol Guldur. They had that whole forest to run around in, if they wanted! But when Sauron’s finally completely gone from the forest, Thranduil only takes a third of it. He gives up 2/3rds of the forest that he could have reclaimed, including giving a good chunk of it to non-Elves who didn’t even seem to be at that meeting. (Meaning, it seems they happily gave away that land rather than it was taken from them.)
Which says to me that Thranduil felt the forest was in capable hands other than his own. I don’t think he needed to stay, once the time of the Elves was fully over, to take care of the forest, because he trusted others to take care of it.
Even accounting for the loss of Elven life (and thus they don’t need more room) doesn’t take away from that Thranduil apparently pretty easily gave away parts of the forest that used to be his home and only kept a fraction of it. I don’t think feeling beholden to the forest would have held Thranduil back from sailing, if he gave up so much of it so readily. He feels a duty to the forest and his people, absolutely, but it doesn’t seem like it’s a “only we can take care of this forest” kind of duty, but instead, “The forest must be cared for, whether by me or someone else.” And those someone elses are there, so I don’t think it would hold him back from sailing.