I have to add a vote for ** Where the Red Fern Grows ** and add a sweet story called ** Desser: The Best Ever Cat ** by Maggie Smith.
To Kill a Mockingbird and East of Eden.
I also usually cry when I read Return of the King, but then I’m a geek.
Of mice and men, is the only book that ever made me cry.
“The Perks of Being A Wallflower” made me cry.
Yes! My wife and I bawled uncontrollably after reading The Cat Who Went to Heaven by Elizabeth Coatsworth. It’s a Buddhist children’s book, but I would never read it to a child.
cold mountain
If you’re a geek, then so am I…oh, wait, I am a geek. Sorry. 
But I always cry at the end of Return of the King. Actually, at the end of The Two Towers, too – I won’t say more because the part in question’s been bumped up into RotK for the films.
The ending of Les Miserables always gets me, too…
First, the last chapters of “The Once & Future King”.
The penultimate chapter ends with a letter to Lancelot from Gawaine telling him the Queen is beseiged. He drops the letter to mount the rescue expedition & Bors picks it up:
–“And at this date my letter was written, but two hours and a half afore my death, written with mine own hand, and so subscribed with part of my heart’s blood. --Gawaine of Orkney”
–He spelled the name out twice, and tapped his teeth. Gawaine. “I suppose,” he said out loud, doubtfully “they would have pronounced it Cuchullain in the North? You can’t tell with ancient languages.”
The last chapter is Arthur’s conversation with young Thomas of Warwick before the last battle. Lerner & Lowe made 3/4 of the book into “Camelot” & Disney animated the first quarter. It’s too bad nobody has made a movie (or movies) of T H White’s version of the old, old story.
Second, a more modern tale: “Now Playing At Canterbury” by Vance Bourjaily. The novel is about the production of a modern opera to open a performance hall in a midwestern university in the 1970’s. It includes faculty, students, townies & outsiders brought in for the production. Oh, & each chapters includes a story told by one of the characters.
In the last chapter, after the production’s over, Henry Fenellon tells Billy (Big Ears) Hoffman how Mona Shapen was killed in Hanoi. Read it yourself if you can find it.
Another fine book, another story that should be told. Or told again.
I have cried when reading The Brother’s Karamazov (Father Zoysima’s speech), Philip Pullman’s His Dark Materials, (Oh Hester, you died so bravely…) and Mark Helprin’s A Soldier of the Great War .
Oh, and Flowers for Algernon. Waaaaaah!
Night by Elie Wiesel.
[spoiler]
When Elie and his father are being marched by the nazi’s nonstop from their concentration camp. No winter clothes. No food. No water. It’s winter. Barely any rest, those that fall asleep die.
And the part that gets me is they are grateful when they arrive at Buchenwald ( or Dachau).
I bawled my eyes out .[/spoiler]
Harry Potter and the Goblet of Fire
In the Tri Wizarding Tourney, when Harry is holding off Voldemort with his wand and all the dead from his life are coming out of the end of his wand…and then he sees his parents come out… I lose it every time.
A Prayer For Owen Meaney
The Wind in the Willows, by Kenneth Grahame.
Especially Chapter 7: The Piper At the Gates of Dawn.
You can read the entire book online (but you miss the illustrations, which is really a shame. Go buy a copy, dammit.
But, to tide you over . . .The Piper At the Gates of Dawn
your humble TubaDiva
Any resemblance to Toad is purely coincidental.
I can’t believe I forgot about the Anne Shirley series.
It sounds like a small thing, but I always cry when Leslie gives Anne the cold shoulder in House Of Dreams because she’s jealous of her baby. Maybe because I know how it’s like to feel that envious.
The part in Anne of Ingleside where Jem feels guilty because he didn’t realize the pearl necklace he gave to Anne wasn’t real always gets me, too. Every single time. And I read those books once a year, every year.
Yet another vote for Where the Red Fern Grows.
Read in the 6th grade, and it absolutely destroyed me.
I’m a little surprised at how many of these are children’s books. Early scarring of the American psyche, I guess. 
And how could I forget A Prayer For Owen Meany? “Oh, God! Please give him back! I shall keep asking you.” Sniff.
Another hand up for LOTR. When Frodo and Sam are struggling toward Mt Doom and…they think they’re going to die but they go anyway…<weeps>
A short story by James Herriot, I think it’s titled A Christmas Kitten? Very sad. Tears.
Tears too in the final book of His Dark Materials–> Iorek’s farewell. I loved Iorek. Again, more tears.
Snicks
I’ll second Night – I remember that affecting me terribly on many levels – made all the worse by the stark truth that it is.
I’m an old softie, so I don’t know how much my vote on anything counts. However, *Grave of Fireflies[/] is one of the most gut-wrenching bawl my eyes out moments I can remember having while watching a movie. And I honestly think I’m going to make it everytime until:
Sato prepares the little girl for creamation and lights the funeral pyre – I shudder and cry uncontrollably every time.
I’d second “Night” as being one of the saddest books I ever read, and I’d like to add Miron Dolot’s “Execution by Hunger,” which is about the Ukrainian famine of the early 30’s. The scenes of the family’s often futile attempts to help their starving neighbors and the devastation inflicted by the Russians as they try to destroy Ukrainian culture are almost unbearable.