For me it's a toss-up.
On one hand there is Galadriel's song as the Nine depart down the Anduin. It wasn't sad to me the first time I read because I didn't understand, but each time it is more so because she expresses the grief of never being able to go home again because of her banishment along with all the rest of the Noldor.
On the other hand, and this one I have to admit is the most sad to me, is that moment when Smeagol watches Sam and Frodo sleeping peacefully beneath the stairs of Cirith Ungol, has just come back from Shelob, and his eyes soften and he almost - almost feels a love and affection for Frodo. Then Sam wakes and shoo's him off, and the moment passes, and Smeagol's last chance at heart-change is gone. The first few times I read that I wanted to yell at Sam. In my later readings it's just sad, because I see that there was never really any chance for it to be different because Sam is who Sam is, and Gollum is who Gollum is. It's just very sad.
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