Cassie and Sam celebrate their honeymoon at a country winery, where they help their hosts deal with a dilemma. Grace encounters her first heartbreak and Abigail holds a joint fundraiser with Mayor Donovan.
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.
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.