Shannara/Tear Jerker

The climax of The Elfstones of Shannara. If it isn't bad enough that after declaring his love for her, Wil Ohmsford is forced to witness and accept the fact that Amberle Elessedil must transform into the new Ellcrys, there is the scene later in the Gardens of Life after everything is over. The moment with the little Elf girl and her mother without weeping openly, especially the lines: "Will she keep the demons far away from us?" "Far away." "And protect us always?" "And protect us always." And a few paragraphs before that: "Something of the self must be given back to the land. In the end, she had given up everything. But she had not lost everything. In becoming the Ellcrys, she had gained an entire world."
- Allanon saying goodbye to Wil is almost as bad. At the start of the book, Wil was warned by his Great-Uncle Flick not to trust Allanon, who he had adventured with before. After Amberle's transformation, Allanon and Wil have a long talk about what happened. Allanon's last words to Wil? "Tell Flick he was right about me. He'll like that, I think." Ow. Just, ow.
Wishsong counts too, for the Magnificent Seven-worthy, OK Corral-ish finale at Graymark, wherein Jair's entire party except himself and Slanter sacrifice themselves so he can reach Heaven's Well. The death of Helt and Garet Jax is particularly poignant. No question of course for Allanon.
There are so many deaths in the Heritage series that it could almost embody this trope. While Quickening, Cogline, and especially Faun's deaths are heart-wrenching, it was the entire slew of losses in Elf Queen of Shannara that rips everyone's heart out. Naturally the loss of Ellenroh and Eowen Cerise was quite a blow, and Garth had me bawling, but even Gavilan brought a few tears. One of the best and most well-written books in the series, but utterly depressing, too.
And then there's The Voyage of the Jerle Shannara. Walker's death, the mutual kill of Ard Patrinell and Tamis, the Woobie-fication of Ahren and Quentin, even Antrax's Alas Poor Villain, and the death of The Mole, Ryer Ord Star got to me. It's just depressing to read.