Cassie gives those around her pieces of jewelry that magically turn out to be just the thing each have been needing. In search of an engagement ring for Cassie, Abigail helps Sam search for the perfect one - a legendary Merriwick heirloom that was thought to be lost forever.
A mysterious song magically spreads across Middleton.
Abigail's father comes to Middleton in hopes of making amends. Cassie helps an expecting couple accept how different their lives, and family, will be once the baby comes. Grace is forced to think about her future and what path she'll follow as she realizes her affinity for math might not be a passion.
Cassie and Sam bring Grace and Nick for an overnight at the lake house, hoping time together will help the kids resolve their differences and help the soon-to-be family bond, but Cassie faces a few obstacles before they start acting like a family again.
Grace finds herself under the spell of Elizabeth Merriwick after Cassie discovers an old trunk filled with her vintage clothing. Inspired by its history, and tapping into her Merriwick heritage, Grace finds a passion for storytelling. Meanwhile, Cassie helps a mother and daughter reconnect over their past at Grey House.
A secretive dating app developer on the verge of a breakthrough checks in at Grey House, capturing the entire town's interest - especially Abigail's.
Cassie has to confront what "'til death do us part" means for her relationship as Sam travels to South America as additional medical aid during a tragic time. Grace digs up some of Middleton's earliest history while revising the town's website, and Abigail shares the same history with her budding romance, Phil.
Cassie sets out to track down Elizibeth Merriwick's original wedding dress, learning a bit from every woman who wore it. Grace and Noah hit a snag in their relationship as Abigail and Phil start to ramp up theirs.
Grace, in a true Middleton tradition, enlists the help of the town in making a magical quilt that's said to grant the wishes of the recipient-and seemingly all that contribute to it. Cassie and Sam learn even more about each other as secrets are revealed.
After a series of unfortunate events, Sam and Cassie have to accept that their wedding might not be as perfect as planned; in light of her almost-romance with Phil, Abigail's quest to put down roots lands her a new job as the mayor of Middleton.