Emily Parker, nearly 25, arrives in Willow Creek, Maryland, after her life in Boston collapses. Her boyfriend Jake, whom she supported through law school by dropping out of college during her junior year, dumped her and canceled their shared lease once he landed a prestigious firm position. Before Emily can regroup, her older sister April is seriously injured when another driver runs a red light, shattering April's right leg. April's 14-year-old daughter, Caitlin, escapes with bruises and a sprained ankle but develops nightmares. Emily moves in as caretaker, grateful for any distraction from her own problems.
Emily drives Caitlin to sign-ups for the Willow Creek Renaissance Faire. A volunteer named Stacey explains that any cast member under 16 needs a guardian to participate alongside them, so Emily must join for Caitlin's sake. She also meets Mitch Malone, a charismatic gym teacher, and Simon Graham, a meticulous young man with a clipboard who criticizes Emily for not completing her audition form. Emily signs up as a tavern wench.
Saturday rehearsals begin with Simon leading sessions on Elizabethan history and character names. Emily chooses "Emma" as her Faire name with minimal thought, irritating Simon. She learns he is an English teacher and that his older brother, Sean, co-founded the Faire with Chris Donovan, owner of a local bookstore called Read It & Weep, 10 years ago. Simon and Emily clash constantly. At home, Emily, Caitlin, and April practice accents by watching movies together, gradually bonding as a household.
While waiting during April's physical therapy, Emily wanders into Chris's bookstore and strikes up a friendship. Simon arrives, and he and Emily share an engaging conversation about Shakespeare, their first moment of genuine rapport. The connection shatters when Emily reveals she never finished her English degree; Simon's visible disappointment makes her feel small, a reaction she associates with Jake.
When rehearsals move to the wooded Faire site, Emily discovers a secluded memorial: a bronze plaque bearing Sean Graham's name, dates showing he died three summers ago at 27, and a line from
Pirates of the Caribbean. She realizes Simon's protectiveness of the Faire and his rigid demeanor stem from preserving his dead brother's legacy. Chris later shares the full story: Sean was diagnosed with non-Hodgkin's lymphoma and died during a Faire run. Simon moved home, took over, and has run the event alone ever since. Emily begins to wonder whether Simon loves the work or has inherited an obligation he cannot release.
Opening day reveals a transformed Simon. As Captain Ian Blackthorne, he wears a pirate costume complete with kohl-lined eyes and a red-feathered hat, his demeanor shifting to confident and flirtatious. Emily is paired with Simon for a handfasting ceremony, a Faire tradition in which couples bind their hands with a golden cord and exchange vows for a year and a day. Simon kisses Emily at the conclusion, a staged kiss that jolts her. She keeps the golden cord, unable to stop thinking about his touch.
The tavern proves severely understaffed. When Simon criticizes Emily for missing performances, she fires back that three people cannot do the work of six. She takes charge, arranges additional volunteers through Chris, and transforms the operation. Simon as Captain Blackthorne visits the tavern daily, engaging Emily in flirtatious banter. One evening, Emily rearranges the tavern tables without permission. Simon is furious, insisting the layout has been the same for 10 years. Their argument escalates until he suddenly kisses her, passionate and real. They make out against the bar until Emily's too-tight bodice causes her to feel faint and Simon loosens the laces. When Stacey and Mitch arrive, both pretend nothing happened.
At Sean's memorial the following weekend, Simon confesses to Emily that at 27, he has reached the age Sean died and feels he does not deserve years his brother never had. Emily shares her own story of being abandoned by Jake. The intimacy breaks when Simon assumes Emily is romantically involved with Mitch and withdraws. Mitch later reveals he has known all along that Simon is interested in Emily and gives her Simon's address. At Simon's house, Emily confronts him. Simon admits he disguised his feelings inside the pirate character because it felt like a loophole. Emily asks whether Simon, not Captain Blackthorne, wants to kiss Emily, not Emma. He says yes. They spend the night together, and Simon tells Emily she means something to him.
Simon promises to "woo" Emily properly. The following Faire Saturday, patrons and cast members deliver roses to Emily throughout the day, each sent by Captain Blackthorne, until Stacey fashions them into a crown. At the farewell show, Simon publicly declares that Emma the tavern wench has stolen his heart. Emily joins him onstage, confirms she has been wooed, and Simon dips her in a kiss to the crowd's cheers. In a quiet moment at the bookstore, Emily reads Shakespeare's Sonnet 29 aloud with Simon, a poem about despair transformed by love. Simon mouths the final couplet against her skin: "For thy sweet love remember'd such wealth brings / That then I scorn to change my state with kings" (265).
Emily's happiness falters when Chris asks her to train a replacement at the bookstore. She fears she is being fired, but Chris explains that she wants Emily to manage the store while Chris spends the winter in Florida caring for her ailing mother. Elated, Emily shares the news with Simon, but his first reaction is to ask whether Chris will return in time for Faire. He does not acknowledge that Emily is staying permanently. Emily erupts, accusing him of prioritizing Faire over everything. Simon retorts that the pirate persona she loves will disappear after summer and the real Simon is the "serious one" nobody wants. Emily tells him that keeping Faire exactly as Sean left it will not bring Sean back and that she deserves better than being someone's second priority. As she turns to leave, Simon grabs her arm and calls her "Emma" instead of "Emily." The slip devastates her. She tells him "Emma's gone" and drives away.
Emily withdraws from Faire. April takes over as her caretaker, and Emily asks Chris to talk to Simon about the burden he carries out of grief rather than joy. Stacey and Mitch convince Emily to attend the final day as a patron. She brings April, and they enjoy the festival until April steers Emily toward the handfasting clearing, where a small group of cast members is gathered. Simon stands in the center wearing jeans and a button-down shirt, completely out of costume. He tells Emily she was right: He has been a ghost since Sean's death, micromanaging Faire instead of living his own life. He announces he is stepping back and letting others share responsibilities. Emily, he says, is the first thing he has chosen for himself in years, and he loves her. Emily says she loves him too. They perform a new handfasting as themselves, with Chris officiating and Caitlin wrapping the golden cord.
One year and one day later, Emily manages the bookstore and has organized a Shakespeare reading group with Simon's students. Simon has relinquished control of Faire, shortening the run from six weekends to four. On their anniversary, he kneels and presents four intentions: sell his parents' house, choose a new home, live in it together, and marry Emily. She says yes.