Winter Stroll

Winter Stroll (2015), the second installment in Elin Hilderbrand’s Winter Street series, continues the story of the Quinn family as they work through love, loss, and holiday upheaval on Nantucket during the holiday season. Building on the events of Winter Street (2014), the novel deepens the emotional stakes as Kelley Quinn and his children confront new romantic entanglements, family crises, and the lingering uncertainty surrounding Bart Quinn’s capture in Afghanistan. The novel addresses themes such as Family Resilience in the Face of Crisis, The Search for Stability and Identity, and Seasonal Rituals as Anchors During Instability.

Hilderbrand, often called the “Queen of Beach Reads” (Heaney, Katie. “How Elin Hilderbrand Became the ‘Queen of Beach Reads.’” The Cut, 2019), is known for her vivid sense of place and heartfelt character work, drawing on her longtime life on Nantucket to bring the island’s traditions and charm to the page. A graduate of Johns Hopkins University and the Iowa Writers’ Workshop, Hilderbrand has written more than 25 best-selling novels, many set in the tight-knit, atmospheric world of Nantucket that serves as the backdrop for the Quinn family’s holiday saga.

The source material comes from the 2015 Hachette e-book edition.

Content Warning: The source material and guide feature depictions of substance use and sexual content.

Plot Summary

The book takes place one year after the first novel. The Quinn family faces new challenges as they gather for the annual Christmas Stroll on Nantucket. Kelley Quinn now runs the Winter Street Inn alone after his second wife, Mitzi, left him for the yearly Santa, George. Kelley remains on good terms with his first wife, Margaret, a famous news anchor, as she helps promote the inn and provides financial support.

Each of the Quinn children deals with personal struggles. The Quinn’s oldest son, Patrick, is incarcerated for financial crimes, while his wife, Jennifer, struggles to raise their three sons while maintaining her career. Kevin has a newborn daughter, Genevieve, with Isabelle, the inn’s cook. Ava, the elementary school’s music teacher, seems settled with her new boyfriend, Scott, a school administrator, but old feelings resurface when her ex, Nathaniel, returns. Mitzi and Kelley’s only child together, Bart, remains deployed and missing in Afghanistan. Nantucket’s Christmas Stroll weekend coincides with Kevin’s daughter’s baptism, so the entire family converges on the inn to attend Stroll events and Genevieve’s baptism.

The novel begins on Friday night for the holiday house tour and tacky Christmas sweater caroling events. Ava attends the caroling event with Scott. Scott invites a friend, Roxanne, to attend, but Roxanne flirts with Scott, making Ava jealous. Roxanne breaks her ankle, and Scott leaves to accompany her to the hospital. At the local bar, Ava runs into her ex, Nathaniel, who tells her he’s still in love with her. From the outside, it appears that Jennifer, Patrick’s wife, is handling her situation well, but she is hiding her pain from the family and using pills to cope with her grief. She knows she is addicted to the oxycodone and worries about what will happen when she runs out of pills in a few days. At the liquor store, Jennifer runs into Norah Vale, Kevin’s toxic ex-wife, who has returned to Nantucket. Yet, she never tells Kevin.

Meanwhile, Mitzi has returned to Nantucket despite being unwelcome there after betraying Kelley. Mitzi and George attend the house tour, but Mitzi is beset with grief over Bart, and George’s lack of empathy for her situation causes a rift between them. Mitzi regrets her decade-long affair with George and longs to reunite with Kelley. Mitzi uses alcohol to cope with her grief, and she leaves George on the tour and goes to the inn intoxicated. She meets Drake, Margaret’s pediatric brain surgeon boyfriend, who has arrived to surprise Margaret. Margaret arrives, surprised to see Mitzi and Drake both. Kelley comforts Mitzi while Drake whisks Margaret away to dinner and bed. Nathaniel drives Ava back to the inn but asks her to kiss him. She refuses and runs from the car, confused about her situation, thinking she might still love him. She needs to talk it over with her mom, but Margaret is distracted with Drake.

On Saturday, the entire family plans to attend the Festival of Trees party at the Whaling Museum. Scott is still at the hospital with Roxanne, leaving Ava without a date. Mitzi spends the morning at the bar, and Kelley must go pick her up, which leads to them sleeping together. George comes to the inn to confront Mitzi, but she is attending the party with Kelley. Margaret lends Mitzi a dress, and although they have been enemies in the past, they seem to repair their relationship. Kevin and Isabelle leave Genevieve with a babysitter for the first time to attend the party, causing Isabelle much anxiety. Jennifer is sad to participate in the party without Patrick, and the pills are the only thing that gives her hope. Drake proposes to Margaret, but she doesn’t answer him yet.

Margaret uses her contacts in the media to obtain classified information on Bart’s platoon, and at the party, she learns from her assistant, Darcy, that news of the missing Marines will break soon. Norah is at the party and corners Kevin. Despite him asking her to leave him alone, Norah kisses him, which Isabelle sees, and she runs from the party. Kevin chases after her, but she disappears. Nathaniel is also at the party, and he invites Ava to the widow’s walk, and they share one kiss. Isabelle and the baby are missing from the inn. Kevin goes to the Castle, another hotel, and finds George there, who agrees to look out for Isabelle. Kelley and Mitzi leave the party and spend the night together. Jennifer speaks with Norah, who has pills for sale, and they arrange a meeting the following day.

Kevin spends the entire night searching for Isabelle, including at the airport. Kelley isn’t feeling well, but he and Margaret go with Kevin for support. Just as they’re considering cancelling the baptism, George finds Isabelle and the baby at the Castle and drives them back to the inn. One of Scott’s friends saw Nathaniel and Ava together at the party, and after taking Roxanne home from the hospital, he confronts Ava. She admits to being confused about their relationship. Scott leaves angry. Jennifer forces her sons out of bed to dress for the baptism. She meets Norah at the gas station and buys 30 more oxycodone pills, which she hopes will last until Patrick is released from jail.

Kevin and Isabelle reconcile, and everyone attends the baptism and lunch afterward. Scott attends but tells Ava he thinks they should take time apart. Ava is Genevieve’s godmother. After the emotional ceremony, Margaret tells Drake that she does want to marry him. During lunch, Margaret receives news about Bart, and they all race home to be together. Darcy reports that one of the Marines in Bart’s platoon escaped, and there’s a good chance the others are alive. Kelley gathers the family to pray, but collapses from exhaustion and must be taken to the hospital. Jennifer calls Patrick in prison to report on the weekend’s events.