A mysterious trunk arrives at Grey House. Cassie explains that the trunk was found at the Art Institute of Chicago and the last return address attached to it was Grey House. Grace opens the trunk and finds a beautiful gown, a khaki suit, an aviation jacket and a pair of boots. Cassie suspects that these eccentric outfits belonged to Elizabeth Merriwick, who owned Grey House in the 1930’s.
At Bell, Book and Candle, Andrew searches the shelves for a new headache cure. He tells Cassie that the spearmint tea she gave him last time is not doing the trick. Just then, Sam walks in and Cassie decides to recommend Andrew make an appointment to see him. In the meantime, Cassie agrees to continue to offering aromatherapy treatments to help treat Andrew’s headaches.
As Grace tries on the aviation jacket she found in the trunk, Abigail is struck by how perfectly it fits her. Grace begins to imagine why Elizabeth Merriwick might have owned such a jacket. Abigail suggests that she may have been an aviation pioneer. Grace is immediately inspired and decides to write a story about Elizabeth Merriwick for her creative writing class.
While Sam enjoys a cup of coffee at the bistro, Stephanie confides in him that someone gave her a negative review on the bistro website. The review has Stephanie paranoid about her food. She decides that the only way she’ll feel better is to find the person who left the review, the online critic named “Gourmet Eater.”
As Abigail reads Grace’s story about Elizabeth Merriwick, she is impressed with how creative the story is. Abigail suggests that wearing Elizabeth’s jacket must have given Grace extra-inspiration. Grace picks up Elizabeth’s boots and says she already has an idea for the second installment of her story.
At Grey House, a woman named Joan is staying with her daughter Mary. Joan is hoping to re-create a photo they took years ago in the back garden. Cassie and George have agreed to do their best to get the landscaping to look exactly the same way it did all those years ago. Cassie also offers to try and track down the photographer who took the original photo. She then suggests that Joan and Mary go downtown to try and find similar outfits to those they wore all those years ago.
Martha asks Grace to stop by her office after school. When she arrives, Grace is surprised to see her writing teacher Mrs. Klein waiting for her with Martha. Martha tells Grace that Mrs. Klein said her story about Elizabeth Merriwick was one of the best stories she’s ever read. Martha insists Grace give her a copy. Martha also tells Grace that she has arranged for a meeting with Grace and a representative from Haverhill University. Grace is excited but she’s also now has a deadline to finish her new story in time for the interview.
Joan and Mary stop by Abigail’s flower shop in hopes of finding similar bouquets to the ones they were holding in their original photo. Abigail asks when the photo needs to be taken, so she can get the flowers they need. Mary says they have to take the photo tomorrow, because she needs to get on the road and back to work as soon as they finish.
After meeting with Martha, Grace rushes to find Courtney so she can tell her about that she got an interview with the representative form Haverhill. Haverhill is Courtney’s dream school and Grace is excited by the idea that the two friends may end up at the same college. But as Grace tells Courtney the good news, Courtney interrupts. Her interview with Haverhill was canceled because they gave her slot to somebody else, and that someone else is Grace.
Later that evening, another package arrives from the Art Institute in Chicago. Inside the package is a book that appears to have belonged with the trunk. As Grace begins to read the book, she realizes that the what she’s reading is the exact same story she wrote about Elizabeth Merriwick. Abigail and Grace are both stunned by the coincidence. Abigail thinks that wearing Elizabeth Merriwick’s clothes must have helped Grace as she imagined the story. Grace however, begins to question if she can take credit for the story or if she should even take the Haverhill interview. Abigail thinks it would wrong for Grace to cancel her interview. She tells Grace the her stories are still original and that she shouldn’t back away from the advantages that come with being a Merriwick.
Cassie and Sam stroll through the park and discuss Andrew’s headaches. Even after Sam consulted a specialist, neither he or Cassie have found an effective treatment. They both begin wonder if the cause may be Andrew’s stress levels. As much he hates to admit it, Sam thinks that if stress is why Andrew is getting headaches, he would probably benefit more from one of Cassie’s treatment.
At City Hall, Grace tries to convince Martha to give her interview to Courtney, but Martha refuses. After her failed attempt to persuade Martha, Grace runs into her mom. Cassie reminds Grace that she shouldn’t be nervous during her interview. She tells Grace that she is kind and considerate and that these traits will come out while she talks to the representative from Haverhill.
Cassie finds the address of the photographer who took the original photo of Mary and Joan. When she arrives at the address, she finds Andrew in the front yard. Andrew tells Cassie that his father was a photographer and that he’d lived there until he passed away. Andrew tells her that he still has a lot of his father’s photography equipment in the garage and might be able to help take the picture for Joan. When Joan shows him the picture he immediately recognizes it. When he was young, Andrew used to help his father with printing. Andrew is sure he has the same camera that was used for the photo and agrees to take the photo.
At the bistro, Stephanie’s mood is much better. She got a five-star review for her chicken noodle soup and also got some great advice from Liam. As she tells Abigail the good news, Martha comes in and places a very familiar order. Stephanie then realizes that Martha is the prickly food critic who gave her the negative review. Martha admits to being “Gourmet Eater,” but says her reviews are merely a public service and were intended to challenge Stephanie to be even better. Martha points out that her negative review of Abigail’s flower shop made Abigail be friendlier to customers. Just then, Liam stops in to see Stephanie and to order his regular iced coffee. Stephanie then realizes that Liam is also a reviewer on her website and he even left a comment, complementing the attractive owner of the bistro. Just then a big smile runs across her face.
Joan and Mary are preparing for their photo shoot with Andrew. Abigail arrives with the flowers while George and Cassie reveal the nearly identical landscaping for the photo. Joan then reveals to her daughter that the reason she wanted the photo the be so precise was because it gave her quality time with her busy daughter. As they talk, Andrew begins shooting the mother and daughter, capturing their tender moment.
Later in the day, Courtney arrives at Grey House to talk to Grace. Courtney tells Grace that Haverhill called her after they interviewed her and that they wanted to offer Courtney a letter of acceptance. Grace then reveals that she told the interviewee that Courtney was kind, full of life and the best friend anybody could ask for. She ended her interview by saying Haverhill would be lucky to have Courtney as a student. Grace then admits that she still doesn’t know where she wants to go to college. When Courtney leaves, Cassie asks Grace about the interview. Grace shows her mother Elizabeth’s journals and reveals that she wrote an identical to story. Grace says that she didn’t feel right taking credit for the stories that already existed. Grace and Cassie both agree that there is nothing wrong with being inspired by Elizabeth Merriwick. The two are interrupted by the doorbell. Cassie is surprised to find Andrew and Mary standing in the doorway. Mary tells Cassie that she’s decided to stay in town for one more day so she can spend more time with her mom and so she and Andrew can go on a date. Andrew also reveals that he’s decided to quit his stressful job and instead, plans to pursue his dream of being a photographer like his father. He thanks both Cassie and Sam for re-introducing him to his passion for photography.