Winter Street follows the Quinn family over three tumultuous days, from December 23 to December 25, as they gather on Nantucket Island for the holidays while their lives fracture and realign.
Kelley Quinn, the 62-year-old owner of the Winter Street Inn on Nantucket, walks into a guest room on December 23 and catches his wife, Mitzi, kissing George, the man who has played Santa Claus at the inn's annual Christmas Eve party for 12 years. Mitzi calmly retrieves two pre-packed suitcases, reveals the affair has lasted all 12 years, and announces she is leaving Kelley for George. She leaves behind her extensive Christmas decorations. Kelley is already in crisis: The inn has no paying guests, his savings have dwindled to nearly nothing, and his youngest son, Bart, a 19-year-old Marine, was deployed to Sangin, Afghanistan, four days earlier and has been unreachable since sending a single text confirming his arrival.
Kelley's three older children from his first marriage to Margaret Quinn, the anchor of the
CBS Evening News, each face their own turmoil. Ava Quinn, 29, teaches music at Nantucket Elementary School and lives at the inn. She discovers that her boyfriend, Nathaniel Oscar, has left for his family home in Greenwich, Connecticut, without saying goodbye, knowing his recently divorced high school ex-girlfriend, Kirsten Cabot, has been reaching out to him. Patrick Quinn, the eldest sibling at 38, heads private equity at Everlast Investments in Boston but has been placed on leave pending an insider trading investigation. His fraternity brother Bucky Larimer fed him inside information, and Patrick invested over $25.6 million of clients' money on the tip. Patrick's wife, Jennifer, takes their three sons to San Francisco, leaving him spiraling into vodka and Vicodin. Kevin Quinn, 36, manages a bar on Nantucket, his confidence diminished by a painful divorce from his ex-wife, Norah Vale.
Kevin harbors a joyful secret: He has been in a clandestine relationship with Isabelle, the inn's French employee who overstayed her au pair visa and was hired by Mitzi. Isabelle is pregnant. Kevin wants to propose but is paralyzed by emotional scars from his failed marriage. On Christmas Eve morning, he calls Margaret, who screams with joy and offers money for an engagement ring.
Margaret, meanwhile, is preparing to fly to Maui with Drake, a pediatric brain surgeon with whom she has a casual relationship. She packs Ava's paper angel ornament, a keepsake she has carried for over 20 years. She monitors escalating casualties in Afghanistan, scanning the lists of the dead without finding Bart's name.
On Nantucket, Kelley spirals. He buys bourbon and cigarettes, posts on the inn's Facebook page that the party is canceled due to Mitzi's affair with Santa Claus, lists the inn for sale, and sets Mitzi's gold lamé jumpsuit on fire in the bathtub. Ava discovers the mess, douses the fire, corrects the Facebook page, and insists the party will go on.
Ava takes charge, recruiting Scott Skyler, the assistant principal at her school who carries an obvious crush on her, to wear the Santa suit. That afternoon, George returns and Kelley punches him in the mouth. George accepts the blow, and over a shared flask of whiskey, explains the affair began during a snowstorm when Kelley was away all night, leaving Mitzi feeling abandoned. George reveals Mitzi has grown tired of innkeeping and wants to become a life coach. Kelley recognizes an uncomfortable truth: He never took Mitzi's aspirations as seriously as Margaret's.
The Christmas Eve party is a success. Scott, adopting a British accent as "Father Christmas," delights guests. Ava hosts for the first time and is startled by a flash of jealousy when she sees Scott and Isabelle posing together. Then Kevin publicly proposes to Isabelle, and the crowd erupts. Kelley sabers a magnum of champagne in celebration.
Late that night, Patrick arrives after missing several ferries, collapsing through the door in tears. Kevin builds a fire and pours whiskey. Ava, Kevin, Patrick, and Kelley share a quiet moment of solidarity. After the others retire, Scott kisses Ava in the kitchen; she kisses him back with surprising intensity before pulling away, confused. She retreats to her room: nothing from Nathaniel.
At CBS, Margaret delivers a holiday broadcast and is intercepted by her assistant, Darcy, with breaking news: A convoy of 45 American troops leaving Sangin has been captured by insurgents. Margaret feels certain Bart is among them. She cancels her trip, secures a private jet, and arrives on Nantucket late Christmas Eve, climbing into Ava's bed with the paper angel and saying nothing about the convoy.
Christmas morning brings an unlikely reunion. Margaret and Kelley sleep together, a reunion both find easy and familiar. Kevin makes Golden Dreams, the cocktail Margaret and Kelley used to share, and the family opens presents and sings carols. When Kevin and Isabelle ask to take over the inn, Kelley reveals he has already begun selling it. Margaret privately offers to buy it, but Kelley resists.
Patrick's situation worsens when Bucky calls to say he has confessed to federal authorities and implicated Patrick. Margaret finds Patrick in distress, advises him to admit wrongdoing, and promises an excellent lawyer. Patrick texts his boss pledging a full confession.
Ava calls Nathaniel and learns he spent the night at the Cabots' house without calling her as promised. She ends the relationship, telling him she needs more love and a sense of future.
The family gathers for Christmas dinner, to which Kelley has invited Mitzi and George. Margaret and Ava prepare a standing rib roast, evoking pre-Mitzi traditions. Kelley tells the story of meeting Margaret at the Metropolitan Museum's Angel Tree, and Margaret produces the paper angel. Mitzi erupts, accusing them of humiliating her, then storms into Kelley's bedroom and finds Margaret's Cartier watch, confirming they slept together. Margaret asks if Mitzi is the anonymous blogger Queenie229, a screen name combining Mitzi's old title as Roller Disco Queen and her Leap Day birthday. Mitzi does not deny it and leaves with George.
During the blessing, each family member silently reflects on Bart: Margaret suppresses her knowledge of the convoy; Ava recalls the troubled teenager whose misbehavior led him to the Marines; Patrick, humbled by his own fall, recognizes Bart as the family hero.
Jennifer and the boys arrive that evening, having never made it to San Francisco. Patrick is overcome with relief. Recalling how Scott once calmly led a grieving student from the classroom after the child's mother died, Ava recognizes what she feels for him and leads him to her room. They kiss intensely but stop short of sex. Later, Nathaniel arrives from Greenwich and proposes on one knee, telling Ava he loves her because being with her is comfortable. She says no. Scott appears in the doorway and walks Nathaniel out.
The novel closes as the family gathers by the fire on Christmas night. Ava plays "Silent Night," and Margaret holds the paper angel, reflecting that her time with Kelley has been magical but that they will not get back together. Then Margaret's phone buzzes: Darcy confirms Bart was on the captured convoy. He and 44 other soldiers have been announced missing. The inn's landline rings. Kelley rises to answer. Margaret intercepts him, kisses him, and says, "I'll stay as long as you need me to."