The Maharal (intro to Gevuros Hashem) comments on how the Torah never says
where souls go after death. The Maharal's point was that the experience was
too foreign to our experience to be conveyed by prophecy. (His exploration
of the limits of intelligence and prophecy, and why intelligence can grasp
things that are beyond the range of prophecy is interesting, but tangential.)
The Maharal points out that the only thing the Torah does say is "so that
your days may be lengthened (idiom)". For while we can't understand what
existance after death is like, being told there will be such existence can
be understood.
The Rambam (Guide to the Perplexed III), and the Maharal (ibid) take this
verse to mean that the reward for doing mitzvos is to persist beyond death,
and the punishment is to cease to exist.
This view is a minority view.
The Talmud states in Tractate Brachos 28b: When R Yochanan b Zakai became
ill... there are two paths before me, one leading to Gan Eden and the other
to Gehennom [hell], and I do not know on which I will be taken, shouldn't I
weep?
We find similar mention of GE and Gehenom repeatedly in the Gemara.
The terms "Gan Eden" and "Gehenom", though, can't be taken overly
literally. GE in this context is not the place with the tree of knowledge
in Genesis 2 and 3. Similarly, Gei ben Hinnom is a valley outside of
Jerusalem (near the green line, in the middle of the modern city) where
children were sacrificed to Molech (a Pagan G-d).
Brachos 48b doesn't refer to two places in the afterlife, but only one --
much like the verse addressed by the Rambam and Maharal. "We found a source
for making a blessing on food, but where is [the source for] a blessing for
[learning] Torah? R Yishmael says: It is learnt by kal vachomer (a
fortiori). If a blessing is said for temporal life, for life in Olam Haba
(the world to come) how much more so!"
Or, Megillah 28b: Anyone who reviews halachah daily is guaranteed to be a
child of the world to come.
We even know "where" the WtC is, Koheles writes (12:7): The dust returns to
the dust that it was, but the soul returns to G-d who gave it. Or Job's
description (19:26): And after my skin is destroyed, without my flesh, I
will see G-d.
In order to resolve these two approaches we have to assume that either GE
and Gehenom are two different parts of the WtC, or they are two different
descriptions of the same place.
An idea I heard from R Aryeh Kaplan zt"l that caught my fancy is that the
two differ subjectively. (I believe it's also in the first volume of the RAK Reader.) To the good, the experience in WtC is pleasant, to
the evil, it is not so. Eden does literally mean "pleasant".
The Valley of Hinom was a place where flesh was mortified. Compare this to
Yeshaia's description of hell (66:24): They shall go and look upon the
corpses of the men who rebelled against Me; for their worm will not die,
nor will there fire be extinguished, and they shall be ashamed before all
flesh.
Yeshaia considered the fire of Gehenom to be shame. This is the conclusion
of R. Kaplan, as well as Ikarim 4:33 and Nishmas Chaim 1:13. The source of
shame is obvious, as the WtC is confronting G-d, with no hope of evasion.
Any sin still embraced stands clearly before you. "Whoever sins once
creates one accuser."
One last thought: we didn't discuss rebirth after the world to come, or the
general Jewish attitude that almost no one is eternally damned.