Tevye's stories are a chronological but disconnected sequence about his life, so this isn't so much a "plot summary" as a "plots summary." Here we go:
"The Great Windfall" begins when Tevye is still a poor wood cutter. One day, he has the good luck to run into a couple of society ladies lost in the woods and to give them a ride to their friend's house in the rich resort town of Boiberik. When he gets them to the right place, everybody there is super-psyched that they're safe and sound. Tevye's reward is a bunch of money and—even better—a cow. He and his wife Golde realize they can get out of the wood cutting business, buy a second cow, and start up a dairy delivery.
In the next story, "The Roof Falls In," the dairy business is going so well that Tevye even has some extra savings. Naturally, he hands over the money to his cousin, Menachem-Mendl, who's got this really great investment opportunity. (Free advice, Shmoopers: never trust anyone selling you on an investment opportunity.) Several weeks later, Tevye still hasn't heard back from Menachem-Mendl. He's probably just so rich and fancy now that he's forgotten all about Tevye, right? Not so much. More like hiding out because he lost all the money and then some.
"Today's Children" starts a cycle that continues through the rest of the narrative—the various marriages of Tevye's daughters. We start with Tzeitl. One day, the butcher Lazer-Wolf asks for Tzeitl's hand in marriage. Tevye weighs the pros and the cons. On the one hand, Lazer-Wolf is old, uneducated, and generally kind of gross. On the other hand, he's rich, his skills are in high demand, and he's got lots of meat to give Tzeitl. (Seriously.) Good enough for Tevye.
Not so for Tzeitl, who apparently has been engaged to Motl, the young village tailor. Tevye is floored that these crazy kids went ahead and made their own marriage plans, but he agrees. After an elaborate and impressive lie to convince Golde, Tzeitl and Motl get married and live poorly but happily ever after.
Time for Daughter #2, Hodl. Sholem Aleichem was clearly running out of clever titles at this point, because the story is called "Hodl."
Tevye takes in Perchik, a young man who is studying… uh, something… in the nearby town of Yehupetz. In exchange, this guy tutors Tevye's daughters. He's a smart guy, even if he does have questionable politics, and Tevye loves him because they can argue about things until the cows come home. Literally. The guy runs a dairy, after all.
This is all great, until Tevye drives out to go meet the guy he's arranged to marry Hodl to. On his way, he bumps into Hodl and Perchik walking around the forest together, and they tell him… duh, that they are engaged, obviously. Immediately after they marry, Perchik goes away to do something political and illegal. He's promptly caught, jailed, and then exiled. Hodl packs up to join him, there's a tearful goodbye, and it's super-sad.
The next story is called "Chava" because it's about a daughter named Chava. It opens with Golde getting on Tevye's case about why aren't there any decent dudes around, because who is going to marry their other daughters? She's got cause to worry, because Chava is secretly getting close to a non-Jewish guy. This secret engagement doesn't end as well as the others. When he finds out, Tevye tells his family that from now on there is no Chava. They mourn for her as though she were dead and no one is allowed to mention or remember her ever again.
Yeah. That's a sad one.
But not as sad as the next story, "Shprintze"! Tevye befriends a wealthy widow and promises to talk some sense into her slacker son, Ahronchik. Ahronchik, naturally, hooks up with Shprintze, the next daughter. Tevye's psyched about this secret engagement: she's into it, he's into it, plus it comes with a million-ruble inheritance. Not so into it? Ahronchik's family, who offers Tevye hush money to make the whole thing go away. Tevye gets over it, but Shprintze doesn't. Like, really doesn't. In fact, she drowns herself a few weeks later.
Phew. Okay, deep sigh. Dab your eyes with a tissue. Moving on.
The title muse has apparently come back to inspire Sholem Aleichem, because the next story is called "Tevye is Going to Eretz Yisroel" even though it's about the last of Tevye's daughters, Beilke. Beilke really scores with her guy, Podhotsur: he's matchmaker-approved, rich, connected, and not even too old. Just one little problem. Podhotsur thinks it's embarrassing to have a dairyman for a father-in-law, so could Tevye just skip town, and here's a bunch of money to do it with?
Time for the next story, "Get Thee Gone." Tevye has just started to get excited about his impending trip to Israel, when he finds out that his son-in-law Motl the tailor has died. Tzeitl and their kids come to live with Tevye. The village mayor brings a mob of non-Jews to Tevye's house and tells him that they have to beat him up and destroy his house. It's nothing personal, though. They just have to make an example of someone, because the government is really into harassing the Jews these days.
Almost immediately after that, a constable rides up to announce that the Jews are being kicked out of the village, and they've got three days to leave. They're packing up, when Tzeitl announces that they can't leave Chava behind. Before Tevye's head explodes with rage, she reveals that Chava has left her husband behind and wants to go into exile with her family. Tevye forgives her, so there's a happy ending after all—if by happy you mean that your house has been destroyed and your people sent into exile. So, sure, happy ending.