In Norwich, England, on December 18, 1334, Cole Christopher Fredrick Lyons (Josh Whitehouse) and his brother Geoffrey (Harry Jarvis) participate in an annual Christmas hawking competition and split up to try and catch the hawk. Cole goes to the woods, while Geoffrey combs the castle for the hawk. On Cole’s way to find the hawk, he encounters an unnamed old crone (Ella Kenion), whom he offers to escort to a shelter. She thanks him for his kindness, and tells him that she will magically send him to faraway lands on a quest and see things like ‘flying steel dragons and horses’ (Airplanes and cars) and ‘magic boxes that make merry’ (Televisions). After her explanation, she gives him a glowing blue medallion and tells him that if he doesn’t fulfill his quest before midnight on Christmas Eve, he will never become a true knight and remain in the present forever – but does not explain the nature of the quest itself.
In the year 2019 on the same day in Bracebridge, a small city in Ohio, a high school science teacher, Brooke Winters (Vanessa Hudgens), who is disillusioned by love, agrees to take her sister Madison’s daughter Claire to the Christmas Castle’s opening, which is the same place Cole arrives in. Cole, confused by the new and unfamiliar surroundings, gets hit by Brooke’s car by accident, and is taken to the hospital, where Officer Stevens (Arnold Pinnock) gets a report from him that he has amnesia and he believes that he’s actually a knight, as he is not in the US system and has no ID. Brooke offers to let him stay at her guest home until he ‘gets his memory back’. On Cole’s journey, he discovers modern day equivalences like radios, diners, manners, and Alexa.