Reddit reviews Dave at Night

The Phantom Tollbooth

Here are two I think that could work that were my favorites growing up:

Dave at Night: An orphan boy goes to live at an orphanage in New York City where everyone is mean to him. He sneaks off into the streets of harlem every night and discovers parties, jazz, a whole cast of characters (takes place in the 1920s).

Chasing Redbird: A young girl lives with her aunt and uncle for the summer and decides to clear the trail behind their house while confronting her own demons (she feels responsible for some tragedies that have happened).