Dicey Tillerman and her three siblings, James (age 10), Maybeth (age 9), and Sammy (age 6), are having a way better life now than they were in Homecoming, the first book in the Tillerman Cycle. Back then, things were pretty bleak: their mentally-ill mom, Liza, drove them to a mall in Provincetown, MA, left them waiting in the car while she went inside, and then just never came back (that’ll make you think twice before asking your parents to take you shopping). Long story short, the Tillerman kids walked and hitchhiked their way to Crisfield, Maryland, where their grandmother Abigail Tillerman, a.k.a. Gram, took them in.
Gram’s crazy, but in an "I’ll show up at your school and play a game of marbles with your friends at recess" kind of way, not an "I’m catatonic in a mental hospital in Boston" way like Liza. The kids don’t care—they’re just happy to have a home. Gram applies for welfare to help raise them, which she hates so much that she slams plates around in the kitchen every time the check comes. Gram’s three kids, one of whom is Dicey’s mom, have all left her in one way or another, so she prepares for Family 2.0 by filling out adoption papers, and at the beginning of the book, the Tillerman kids are holding their breath (figuratively, not literally) waiting for the adoption to go through.
In the meantime, they’ve started school in Crisfield, their new hometown, and it’s not going smoothly for any of them. Dicey’s a tomboy and a loner, and she has no desire to fit in with the other girls. James is a super-genius, and even in the gifted class, he has to dumb it down so the other kids won’t bully him. Sammy gets into fights all the time, which we later learn is because his classmates are making fun of Gram. And Maybeth has serious learning disabilities and is struggling to learn how to read. The fact that all their teachers are pretty clueless doesn’t help matters.
Dicey has two places of refuge: the barn behind Gram’s house, in which she’s found a sailboat to restore, and Millie Tydings’s grocery store, where she works after school. But there’s a roadblock on the way to Millie’s: Jeff Greene, a 10th-grade boy who sits outside school and plays his guitar. He takes an interest in Dicey and starts singing to her, and she alternates between wanting to sing along and wanting to get the heck outta dodge. After all, she’s not ready for the boy-girl stuff.
Welcome to the coming-of-age component of Dicey’s Song. Dicey’s body is maturing, and she’s not too happy about this whole breasts thing. She’s also not thrilled that her siblings don’t need her as much anymore now that they have Gram, because if she’s not a caretaker, who is she? And then there’s Mina Smiths, a popular girl who insists on trying to be her friend. Add in the constant money worries and, oh yeah, the catatonic mother languishing in a mental hospital in Boston, and you can see why a girl would just want to hide in the barn with her boat.
But wait! Mr. Lingerle comes along, and thinks start to change. Mr. Lingerle is the only cool teacher in the book. He teaches music at Maybeth’s school, and when he realizes the little girl who can’t read is a piano prodigy, he starts coming to the house to give her free piano lessons. He’s an obese man who’s very lonely, and Gram decides to open up her home and heart to him. Through watching their friendship develop, Dicey learns the importance of reaching out to others. Slowly but surely, she starts to do the same with Mina, and even a little bit with Jeff, though when he asks her to the school dance she freaks and says she’s too young for all that jazz.
One day Dicey finds Gram packing a suitcase for the two of them, and they head to the airport for Dicey’s first plane trip. Gram won’t tell her what’s up, but because they’re going to Boston, Dicey knows it has something to do with her mother. When they arrive at the mental hospital, Dicey learns that Liza is dying. She, Gram, and Liza’s doctor are the only ones there to say goodbye.
Dicey’s Song ends with the Tillermans burying their mother’s ashes beneath the mulberry tree in Gram’s front yard. After the makeshift funeral, Gram finally allows the kids to go into her previously-forbidden attic, where they pull down photo albums and gather in the living room, where they look at family snapshots while waiting for Mr. Lingerle to come by with their first pizza (for realsies: they’ve never had pizza). Gram begins to tell them stories about their mother and their uncles John and Bullet, setting the scene nicely for the next book in the Tillerman Cycle (which, in case you’re curious, is called A Solitary Blue.)