A Long Way from Chicago by Richard Peck, 1998.
Joey and Mary Alice live in Chicago during the Great Depression, but every summer, they go to stay with their grandmother in a small town in Illinois. At first, the kids think that staying with their grandmother will be boring, but they soon find out that Grandma is anything but. She’s an eccentric woman who doesn’t let anyone boss her around and doesn’t have much respect for any rules but her own. Although she’s pretty tough, Joe and Mary Alice learn that, deep down, Grandma really does care about other people and tries to help them, even though she often gets into a lot of trouble in the process. Each chapter is a short story from each of the summers that the kids spend with their grandmother, from 1929 to 1935:
Shotgun Cheatham’s Last Night Above Ground (1929): When a reporter comes looking for information about a recently deceased local character, Grandma volunteers to hold a wake for him in order to teach everyone a lesson about truth and gossip.
The Mouse in the Milk (1930): When a group of local pranksters needs to be punished, Grandma decides to play a little trick of her own to get even.
A One-Woman Crime Wave (1931): Grandma turns to trespassing and illegal fishing in her quest to feed the hungry.
The Day of Judgment (1932): Grandma enters a baking contest at the county fair for the glory of her home town and a chance to ride in an airplane.
The Phantom Brakeman (1933): Mary Alice tries to help a young woman escape from her abusive mother, and Grandma brings a ghost story to life for the sake of young love.
Things with Wings (1934): Effie Wilcox, a neighbor of Grandma’s, loses her house to the bank, but Grandma comes to the rescue by demonstrating the power of rumors.
Centennial Summer (1935): As Grandma’s town celebrates its centennial, Grandma decides that uppity Mrs. Weidenbach, the banker’s wife, needs to be taught a lesson.
The Troop Train (1942): Joe, now much older, has enlisted in the Army Air Corps during World War II. As the train taking him to his basic training passes Grandma’s town, she’s there to wave to him.
During the course of the stories, the author includes details about how Prohibition and the Great Depression affected people and other details about life in the early 1930s. This book is a Newbery Honor Book. There are multiple copies available online through Internet Archive.
#5 The Mystery Off Glen Road by Julie Campbell, 1956.
Soup by Robert Newton Peck, 1974.
Some of the stories are laugh-out-loud funny, and some of them have kind of a moral lesson to them, like the time when Rob realized that he didn’t have the heart to lie to his mother even if it would allow him to escape punishment for talking back to the school nurse, the time when Soup and Rob tried to cheat Mr. Diskin out of some money so they would have enough to go to the movies but ended up feeling guilty, and how the boys made themselves sick by attempting to smoke cornsilk. Others are just stories of childhood events and friendship, like the story of how Rob and Soup played football and how Soup loaned Rob his new shoes when his were ruined. Even though Soup often got Rob into trouble, he really was a good friend and went out of his way to make Rob feel better when he needed it the most.
The Best Christmas Pageant Ever by Barbara Robinson, 1972.
Although the Herdmans don’t get the cake Charlie mentioned and have little interest in Jesus, they begin to be fascinated by the description of the pageant and decide to stick around. The Herdmans love movies, and the idea of being in any kind of play strikes them as fun. Although the Christmas pageant basically goes the same way every year, typically using the same kids for the same parts, once the Herdmans make up their minds that they want the starring roles, they manage to push and bully their way right into the center of everything.
At first, the more conservative adults in the church are horrified at the prospect of what the wild Herdmans might do on Christmas itself, but the minister and the lady overseeing the pageant decide to give the Herdmans a chance. As the title says, it ends up being The Best Christmas Pageant Ever as the Herdmans unexpectedly bring out parts of the Christmas story that the other people who had taken the story for granted hadn’t really thought about much: the simple human reactions of a poor young couple who were strangers in a new town, the fear and expectation that accompany doing something great but unfamiliar and confusing, and the sense of wonder and surprise that are at the heart of the Christmas season.
Something Fishy at MacDonald Hall by Gordon Korman, 1995.
MacDonald Hall Goes Hollywood by Gordon Korman, 1991.
The Zucchini Warriors by Gordon Korman, 1988.
The War with Mr. Wizzle by Gordon Korman, 1982.
Beware the Fish! by Gordon Korman, 1980.
This Can’t Be Happening at MacDonald Hall by Gordon Korman, 1978.