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Cassie plays host to Henry, a dashing stranger, and Olivia, a visiting poet. To help with her mounting workload, Abigail offers Grace an internship in the mayor's office, where Grace butts heads with an ambitious fellow intern.
Cassie uses her magic to help two best friends reconnect. Martha is reinstated as mayor of Middleton and celebrates by commissioning a portrait of herself, and challenging Grace and Luke on the history of Middleton.
Cassie, Grace, and Abigail embark on a road trip to Cassie's alma mater, Wellingsly College. There, Cassie reconnects with an old friend, who's contemplating her future as a professor.
Martha and her husband Tom arrive at Grey House for a weekend staycation…or Greycation. There, they engage Cassie and Sam in a couples' party game – which causes Cassie and Sam to realize that they still have some things to learn.
When Laura takes over an injured teacher's class, Almanzo starts seeing her in a new light.
Plans for a new life are threatened when widower Jonathan Garvey and his son are harassed by young toughs.