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|"Is this all real? Or has this been happening inside my head?"
The subject of this article is of a real-life person, place, group, company, product, or creative work that has been mentioned "in-universe" in a canon source. The Harry Potter Wiki is written from the perspective that all information presented in canon is true (e.g., Hogwarts really exists), and, as such, details contained in this article may differ from real world facts.
The Plymouth Settlement, also known as the Plymouth Colony was an English colonial venture to North America. They begun travelling to the New World from 1620 to 1691. One such venture had a party of four wizards including Chadwick and Webster Boot and a No-Maj James Steward. They went on to become founders of Ilvermorny School of Witchcraft and Wizardry.
The Plymouth settlement first set sail in 1620. One of the later adventurers were four wizards leaving Britain in search of an adventure. Mr and Mrs Boot took their two young sons Chadwick and Webster Boot with them. They befriended James Steward. This settlement made a home somewhere near the woods which was by Mount Greylock. One day, the young family went into the woods for their adventure and never returned. They had been attacked by a Hidebehind who killed Mr and Mrs Boot. Chadwick and Webster were saved by Isolt Sayre. James Steward later went into the woods to find the family when they never returned. However, he ended up staying with Isolt and the children in Mount Greylock and never returned either. It was here that they founded Ilvermorny.