Crossland High School is a high school in the town the series is set in. Crossland has a haunted house every year. Greg desperately wants to go to Crossland High instead of Bishop Garrigan Academy. It is also one of the two high schools in Greg's area, the other being Bishop Garrigan High School (only in the online book).
- Rodrick Heffley
- Heather Hills
- Lenwood Heath (Possibly)
- Ward (Online book)
- Andrew Hatley
- Bill Watson
- Unidentified Rodrick's Friend (i)
- Unidentified Rodrick's Friend (ii)
- Kathy Nguyen
- Leonard Harrington
Crossland High School doesn't appear physically in any of the books or the films, but it is mentioned several times in the books.
- in the online version of the book, Greg wishes to go here, as (unlike Bishop Garrigan) it is co-ed
- in the first book, Greg attends their "Haunted House" attraction on Halloween. He gets scared in an area called "chainsaw alley", and his mother makes the chainsaw guy apologize for scaring her son.