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I read a series of books when I was in Middle School, ~1991, that centeret around a young boy who was sent off to a boarding school, and the books detailed his adventures at the school. The kid was very unhappy to be at the school and regularly attempted to escape. I remember one scene where, upon having his batting skills noticed, he was placed into the school's baseball team. On the first away game, he hit a home run, ran for first place, and kept running into the forest beyond the field.
In general, he was characterized as a very bright and athletic kid, who was completely disinterested in the school and those activities, and was nonetheless caught up in adventure after adventure. There was a female boarding school across the road, which led to a few situations as well.
I know it's a very vague description, but I was hoping someone would remember the stories as well and be able to tell me the author or title.