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The time is way after Hiccup and his group, the descendants of the group carry on with the tradition and make sure it stays in the town as well.
Ruffnut and Tuffnuts Descendant:
Light Fury-F- @CheekyCookie
Kayne-F-Night Terror- @XxxHorror-CatsxxX
Name-Gender-Age-Role (Descendant of one of the main 6 [ONE PER PERSON]? Or Towns-person?)-Dragon and dragon name- crush - other