The Tillerman Cycle is a seven book series by Cynthia Voigt following the eponymous Tillerman family.
At the start of the series, thirteen year old Dicey Tillerman and her siblings, ten year old James, nine year old Maybeth, and six year old Sammy, are abandoned by their mother Liza, who simply parks the car in a parking lot, says she'll be back, and then never returns.
The first book, Homecoming, follows Dicey as she shepherds her siblings across the state, looking for a relative none of them have ever met in the hopes that she will take them in. For months they face trials like hunger, exhaustion, strangers both friendly and unfriendly, family strife, law enforcement, and despair as things don't go according to plan.
The first, second, and sixth and seventh book all follow the current Tillerman family, with the first, second, and seventh following Dicey specifically. The sixth book, Sons From Afar, follow an older James and Sammy.
The middle books follow the people around the Tillerman family, be they Dicey's friends or Tillermans in the past. While the first two books are in chronological order, and the last one is definitely the last one, the middle books are not. A Solitary Blue and Come a Stranger both include the entire backstories of Dicey's new friends, starting with their childhoods and leaving off in the "current day" where Dicey is. The Runner takes place entirely in the past several decades before the rest of the series, and follows Dicey's now-deceased (but still somewhat present) uncle Bullet.
Homecoming, in which Dicey and company travel across the state to find a family that doesn't know they exist, and wind up finding more than they expected along the way.
Dicey's Song revolves around the kids adjusting to life in a new town after they've settled in. Dicey, used to being the "adult" in the family finds herself suddenly able to be a kid, and she's not used to it, and everyone needs to make adjustments. The kids had always been loners and thought of badly by the people around them (Sammy, though deceptively charming when he wants to be, has a temper and acts out, James is too damn smart and socially awkward, Dicey is highly pragmatic and doesn't care what anyone thinks-- even when she should, and Maybeth has a learning disorder coupled with shyness, leading others to consider her pretty and brainless). Now Dicey and the others have to learn how to open up, both to strangers and to their new family.
The Runner takes place a decade or so before the other books and follows Dicey's uncle, Bullet, who is dead before the series proper starts. Bullet is a track runner at school and has Sammy's temper and Dicey's uncaring attitude towards anyone not directly related to her, and then doubles it by disregarding what his family thinks as well. This leads to him ignoring the racial boundaries at his school and befriending the first black kid allowed on the track team, Tamer Shipp, but also gets him into trouble with authority figures.
A Solitary Blue is actually the first book I read in the series and the first book to ever make me cry. It has the entire backstory of Dicey's eventual love interest Jeff Green as he too deals with maternal abandonment (his mother left to join the hippie movement) and tries to grow up with a well-meaning but distant father, and then deal with the disillusionment of when his mother actually comes back...
Come a Stranger features Wilhelmina "Mina" Smiths, Dicey's best friend. Unlike Dicey, Mina is popular, well-off, and from a respectable and wholesome family. She's also black, which leads to some racial tension and uneasiness. However, she finds a friend (and crush) in her Reverend father's associate, Reverend Tamer Shipp (the same Tamer Shipp from The Runner). From him, she learns about Bullet Tillerman, and connects the two families together (befriending Dicey along the way). Like with Jeff's story, Mina's is tied to the Tillerman family, but is centered solely around Mina and her own character's growth.
Sons From Afar follows James and Sammy as they try to find their long-missing father, Francois Verricker (whom the reader only ever sees once in The Runner). The book takes place a few years after the events of Dicey's Song, and James and Sammy -- already fairly distinctive characters-- have grown steadily in the opposite directions of each other. James is quiet, thoughtful, highly intelligent, and a bit of a coward. Sammy is more athletic and headstrong, and less likely to think things through. Together the two reforge their slowly fraying familial relationship while running around looking for ties to Verricker.
Seventeen Against the Dealer is the last book in the series and takes place after Dicey, now 21, has dropped out of college to build sailboats (a running theme through the books, and a callback to one of the most memorable scenes in Dicey's song.) Unfortunately, business isn't going so well, and as Dicey gets more and more absorbed in her work, things like family and friends all start to fall into the background...
These books hold major nostalgia value for me. Maybe it's my rose-colored glasses, but I remember them being good, even touching.
On a very, probably unseemly, personal note; I was about eleven/twelve when I first read Homecoming. My folks were going though a very messy divorce. Mom was an alcoholic. After a point, dad wasn't there. And I was the one caring for my younger sibs. Dicey got me. Jeff got me. The situations weren't the same, but there were enough notes that rang true that the books really spoke to eleven/twelve year-old-me. These books are always going to hold a special place in my heart.