Brandon looks for means to quell Tara's need to have a baby. Abigail is too busy campaigning against Stephanie in a heated competition for festival queen. Upon arrival, Cassie realizes that, despite her efforts, there are many distractions at the lake house. She befriends Cassie and makes some effort to defend her. Meanwhile, Cassie sees Nick and Grace's feigned truce start to crumble and arranges to have them work together. Later in the botanical gardens, it is discovered someone cut a stalk off the Merriwick and it seems its decline affects the ladies in town. Abigail shows Phil around town, and, as their romance blooms, he considers moving there.
She must decide if what she really wants is right at home. She invites the children into her house to take care of Lori's knee. She tells them she had just moved in, and plans to open a shop on Main Street. Sam is excited for Nick to have an old friend around but is puzzled by his son's lack of enthusiasm for Noah's return. Cassie is caught in Ashley's lies and Middleton's new mystery.
Cassie later meets with Ryan to put the past behind them, but suddenly finds herself questioning if she is ready for a new romance with anyone. However, John pressures her to join him on his adventure in the , and her future remains in question. Meanwhile, she welcomes popular fantasy author Jessica Carrington and her editor Sean to Grey House. A man claiming to be from the delivers her a package sent from out of the country that was lost for 20 years. Meanwhile, Grace postpones her driving test before her last road lesson, prompting Sam to question her motives. However, Cassie keeps the mayor distracted by helping her plan a surprise of her own for Tom.
In the sequel, , the map on the wall in the police station shows Middleton located northwest of Chicago, in the vicinity of. Jake is fascinated by Cassandra, but as opposed to her intuitive decision-making, he relies mainly on facts. Grace's friends, Nick and Courtney, whisk her away for a day of celebration, but she longs to spend time with Cassie. Back in Middleton, Vanessa and Michael's wedding plans have spiraled so far out of Elizabeth's control that the couple abruptly cancels the entire affair. Grace plans to make a long-distance relationship work after Noah is accepted to college in New York, but, when she starts sacrificing major events in her life, she realizes their relationship may change after graduation. Later, as Harrison readies to depart Grey House, he leaves behind one painting as a gift, surprising everyone as those depicted are hardly doing anything at all.
Cassie introduces her to a handsome attorney who seems almost too perfect — proving Cassie's plan isn't complete. Also, Cassie helps Jessica and Sean discover their long-simmering love for each other. She tries to bring the anonymous two together, getting help from Sam, who is concerned that one's questionnaire indicates a medical condition. He has an opportunity to right a wrong, which helps put the past behind them. Meanwhile, Stephanie seeks out a customer who left her bistro a bad review, which leads to a surprising culprit.
With her signature charm, Cassie attempts to bring everyone together, ensuring all of Middleton is in for new changes, big surprises and, of course, a little bit of magic! Abigail offers to help Sam cook dinner for his date with Stephanie, but, when Abigail doesn't show, Cassie saves his dinner plans. Inside the botanical gardens, Sam realizes Cassie and the Merriwick are connected and shares with Martha that he believes in Cassie. When a Grey House guest claims a ghost is haunting his room, Cassie knows a deeper problem lurks and promises he can trust her to solve it. The couple spend a romantic evening at Grey House where they kiss. However, the demand for her chocolates exhausts her.
Meanwhile, Sam declines the hospital's generous job offer, deciding time with Nick is more important. Meanwhile, in an effort to keep Sam from letting Cassie slip away, Joanne encourages her brother to focus on the good things in life instead of worrying about the bad things that could happen. At Grey House, guest Alexis finally admits to Cassie about her financial falling out from her father but promises to settle her bill. Abigail's father Arthur , who walked out of her life 22 years ago, returns. The experience weighs heavily on him, and Cassie offers support while giving him needed space. Meanwhile, Abigail feels a connection with the app creator, but she is thwarted when he accuses her of stealing his idea. However, Ryan decides to take his business to Blairsville.
At the Bistro, Abigail approaches Stephanie with a business proposition, before scheming a startling betrayal. As time passes, some people in Middleton continue to be hostile toward Cassie and she considers leaving town. George accidentally reveals Sam and Cassie's pseudo-secret that they are officially together, causing Grace to feel hurt as she wasn't told first. He finds a most unique vintage ring, which unbeknownst to him is a Merriwick family heirloom. At the same time, Martha is visited by her son, Michael. Grace shows her that listening, offering advice, and caring for each customer, as Cassie does, is what helps them find exactly what they need.
Sam and Nick begin working on their damaged relationship. Meanwhile, Abigail speeds along a building permit process with Martha, hoping Phil will move his business to Middleton. The mother of the bride, Elizabeth , arrives in town, decides Martha's plans aren't elegant enough, and takes over, leaving Martha feeling left out and dejected. Eve fears Grace will replace her as Sam's receptionist, but Grace puts a plan in motion to help restore Eve's confidence. Meanwhile, after Sam finally gives Nick permission to go to London, Grace senses her friend is having second thoughts about leaving his dad, but her plan to help him could backfire. Abigail, as new mayor, tries to outdo Martha, whom she replaced, and creates rivalries within the town.