During a chocolate festival at Grey House, Cassie hosts Kenny "the chocolate king", whose big persona hides his insecurities about taking over the family business from his father. Sam butts heads with the new hospital administrator when he goes around him to hire a new surgeon. Abigail gets a surprise proposal from an old college friend who makes an unexpected visit. Joy's former business partner arrives at Grey House to formally dissolve their partnership. Inspired by an answer at a local trivia night, Sam and Donovan uncover a new clue surrounding the Merriwick-Davenport curse.
A mysterious, darkly beautiful woman named Cassandra Nightingale moves into an old, abandoned house which is reputed to be haunted by its original owner, "The Grey Lady". The small community is divided in their opinion of her: Some want her to stay (especially widowed police chief Jake Russell and his two children), while others want her to leave. Through the course of the story, seemingly magical things happen, and the community attributes these occurrences to her. Everyone begins to wonder if she is really a witch.