How It All Goes Down
The Tillerman children—Dicey, James, Maybeth, and Sammy—are on a car trip with their mother heading from Provincetown, Massachusetts to Bridgeport, Connecticut. There, they're hoping to get help from their rich Aunt Cilla. Times have been tough and Momma Tillerman has just been acting weird lately.
So maybe it's not a complete surprise when Momma stops at a mall in the middle of Connecticut and tells the kids to wait in the car… and then never comes back. This leaves thirteen-year-old Dicey in charge. She decides that her siblings should keep going to Bridgeport because that's what Momma wanted. They have about seven dollars in their pocket and they can probably walk there in a few days. Easy, right?
Turns out walking nearly eighty miles with a thirteen, ten, nine, and six-year-old, isn't as easy as it sounds. The kids walk for days, sleep outside, and go to bed with empty tummies as their money runs low. At Rockland State Park, where they stay a few days, the kids fish and meet up with Louis and Edie, two teenage runaways. Sammy also tries his hand at stealing food, but Dicey won't have it—Tillermans aren't thieves, thank you very much. Dirty, tired, abandoned street urchins, yes; thieves, no.
The kids are able to earn a bit more money carrying people's groceries to their cars and they keep moving on. In New Haven, they meet college students name Windy and Stewart, who feed the kids and agree to drive them to Aunt Cilla's house in Bridgeport. Things go a little south when James steals some money from Stewart, but all is forgiven and the Tillermans load up in the car to head to their destination. Yay. Finally, a break.
But not so fast: Bridgeport isn't what they expected it would be. Aunt Cilla isn't rich—but worse than that, she isn't even alive anymore. Her only daughter, Eunice, lives in the house. Trouble is, she's a devout Catholic who's studying to be a nun and isn't really suited to care for four abandoned children at the drop of a hat.
When Momma is found in a catatonic state with no hope of recovery in a mental hospital, Eunice, with the help of her spiritual advisor, Father Joseph, agrees that it is her Christian duty to take in these poor motherless creatures. But maybe not Sammy since he's such a troublemaker… Yeah, he definitely has to go.
Dicey isn't so thrilled by this deal; she really wants to find a way to keep her whole family together in a place where they can be happy. So when she hears Eunice mention that they have a grandmother—Abigail Tillerman—in Crisfield, Maryland, Dicey decides that maybe the kids should check this lady out. How bad could she be?
After saving up a whole bunch of money for the trip, the kids set off by bus. They rely on the kindness of strangers again when two teenaged boys named Tom and Jerry sail them across Chesapeake Bay. But things get really scary for four little kids out on the road all alone when they decide to try to earn some extra money picking crops in some fields they pass.
A landowner named Mr. Rudyard hires them, but it's obvious this guy is an odd duck, and he takes a strange liking to Maybeth, too. When he makes it clear that he's about to attack the Tillermans, the kids are forced to make a run for it. They manage to find help and some sympathy at a nearby circus with Will and Claire, who protect the kids from Mr. Rudyard and offer to drive them the rest of the way to Crisfield. More lucky breaks—phew.
In Crisfield, Dicey finds out that Abigail isn't the most loving and caring grandmother in the world. She knows exactly who Dicey is (turns out Cousin Eunice wrote to her to let her know the kids were making a break for it), but she won't let them stay with her. She isn't totally heartless, though, and she lets them spend the night since they have no place to go. Gee, thanks Gram.
Dicey is working on a master plan: If the kids can just convince their grandma how awesome they are, then maybe they can win her over and win themselves a home in the process. They start doing odd jobs around the house for the next few days, but it's no use—Abigail just can't take them in. She was a pretty bad mother to her own children, which is why they all left, and now she just can't take the chance that she might drive away more people who she loves.
Dicey feels defeated but understands. Cousin Eunice's it is then. Abigail plans to write to Eunice so the kids can head back to Bridgeport, but in the meantime, she lets them stay and enrolls them in school. One day, Dicey realizes that her grandmother never mailed the letter to Eunice. And then she tries one last time—Abigail really should let them stay, shouldn't she? Four sets of adorable puppy dog eyes win the day, and Abigail admits that she cares for her grandchildren and wants them with her. Now, who's ready to go home?