Shavuot is the holiday about the giving of the Torah at Mount Sinai (matan torah). There is a tradition of late-night study called tikkun leil Shavuot, or colloquially, a tikkun.
The Pittsburgh community has -- I'm told this is very unusual -- a community-wide tikkun for the first few hours, from 10PM to 1AM. There are about 25 one-hour sessions (spread across the three timeslots) with teachers from across the local Jewish spectrum -- rabbis, cantors, and educators; Orthodox, Reconstructionist, Reform, Conservative; from synagogues, schools, social services (like eldercare and prison support), and other Jewish organizations.
I went to a session called "relearning Leah" that was very good. We only had an hour and there was a lot of discussion, so we were mostly in the Torah text about her deceptive marriage and children and didn't get much into the midrashim. Something I noticed for the first time in how Leah explains the names for her sons:
Reuben: "It means: 'GOD has seen my affliction'; it also means: 'Now my husband will love me.'"
Shimon: "This is because GOD heard that I was unloved and has given me this one also".
Levi: "This time my husband will become attached to me, for I have borne him three sons."
And then (B'reishit 29:35):
She conceived again and bore a son, and declared, "This time I will praise GOD." Therefore she named him Yehudah. Then she stopped bearing.
The first three were born of, and named for, her distress, and each time God gave her another son. With Yehudah she seems to have come to terms with her situation; she doesn't name him for distress but instead praises God. She seems to be happy with her four sons despite everything. I don't think God would punish her for that, so I think the fact that this was her last son in this batch is more like closure, maybe. Later Leah produces, by proxy and directly, four more sons, named for luck (Gad), fortune (Asher), "my reward" (Yissachar), and "a choice gift" (Zebulun) -- all positive/praise, not distress.
I also went to a session called "Midnight midrash: outlandish stories of Caesars, magic, and mosquitos", because how could you not? This rabbi did "midnight midrash" last year too (different topics) and I really liked his teaching, so even though I try to go to new-to-me teachers at the community tikkun, I went to this because of last year. It was both fun and educational, but I think I'd have to reproduce the handout to explain why.
I changed synagogues last summer, so this year found out for the first time about Beth Shalom's traveling tikkun. After the community-wide one ended, about twenty of us headed to our rabbi's house, where we learned some Rambam on laws related to teachers and students. Around 2:30 that ended and about eight of us headed to the home of a congregant who planned to study all night and then, with whatever stragglers were left, go to the dawn holiday service before crashing. This congregant's tradition is to study a different minor prophet each year in detail. This year it was Habakkuk, which I probably hadn't read in its entirety since I was in high school. Unlike many prophets, Habakkuk isn't preaching to Yisrael; he's exclusively interacting with God and he initiates. I would summarize it as: Chapter 1: why is this bad stuff happening to us? Chapter 2: don't worry; God will afflict the people who are afflicting you and you'll be ok in the end. Chapter 3: a psalm in praise of God. There are, of course, a lot of details in there, and we had a good discussion that I can't summarize. We reached a natural pause around 4:15, at which point I was fading, so I left at that point (I was not the first, at least) and I don't know if they dove into more commentaries or looked at something else. I wonder how many made it to the early-morning service.