Fourteen-year-old Dexter Green is a caddie at the Sherry Island Golf Club, a popular summer destination for the wealthy citizens of Black Bear, Minnesota. Throughout the year, Dexter occupies himself with memories of previous summers at the club and looks forward to the next summer there. He is particularly lost in reverie during the Midwestern winters, which are long and dreary and leave the golf course covered in deep mounds of snow. His memories of summers at the club are often blended with “winter dreams,” including fantasies of being a man as prominent as Mr. Mortimer Jones, but even more wonderful, and an even better golfer than the club’s best athlete, T.A. Hedrick.
One day, Dexter has his first conversation with Mr. Jones, after Jones learns that Dexter will quit caddying at the club. What Mr. Jones does not know is that Dexter is quitting due to an incident on the course with Jones’s “beautifully ugly” eleven-year-old daughter, Judy Jones, which left Dexter feeling insulted.
The narration skips ahead nearly a decade. Dexter has returned to the golf club, but he now is playing on the course. He left Black Bear to go to an “older and more famous university in the East,” instead of the state university where he had expected to take “a business course.” He returns home to open a small laundry, which he expands into a chain of laundries. This makes him, at twenty-seven years old, the owner of “the largest string of laundries in his section of the country.”
While on the golf course, he reunites with Judy who, according to Dexter, has grown into an “arrestingly beautiful” twenty-year-old woman. Through his golfing companion, T.A. Hedrick (with whom he is now unimpressed), he learns about Judy’s reputation for promiscuity. Later that evening, while swimming in the lake, she comes upon him in her motor-boat and introduces herself. She invites him to dinner at her house the next evening, and Dexter envisions Judy in a glamorous evening gown with a butler presenting cocktails, though neither of these things happens.
During dinner, Dexter talks about his years at university and his newly found wealth, which puts Judy at ease. She dismissed her last beau after finding out that he was poor. Judy decides rather quickly that she has fallen in love with Dexter and he returns her affections, but soon doubts her sincerity after seeing her go off with other men. Their relationship is characterized by moments of intense ardor followed by a cooling of affections. Dexter asks Judy to marry him. She half-heartedly accepts, then becomes involved with a New Yorker whom she promptly dumps.
After Judy leaves town to travel, Dexter becomes engaged to someone else, Irene Scheerer, a “light-haired…sweet and honorable” girl whose family welcomes him. Still, he persists in thinking about Judy who “had treated him with interest, with encouragement, with malice, with indifference, with contempt.”
A week before announcing his engagement to Irene, he sees Judy again at a dance at the University Club. Her absence had allowed Dexter to believe that he could move on, but once he sees her again he is “filled with a sudden excitement.” They leave the dance in her coupe and spend the night together. He quickly breaks his engagement to Irene to become engaged to Judy, a commitment that lasts only for one month.
After several years of entertaining the possibility, he decides to sell his laundries and move to New York. His plans are briefly interrupted by the First World War, which he enters as an officer, but he finally moves back East.
The narrative relates a final incident in Dexter’s life which occurs when he is thirty-two. He has a visitor from Detroit, Devlin, a business associate who knows Judy, as he is best friends with her husband, Lud Simms. Judy moved to Detroit to be with Simms who “drinks and runs around,” despite her and their children. Dexter is surprised by the news and even more surprised by Devlin’s assessments of Judy – that she is too old for Simms and that her looks have faded. The knowledge is devastating and Dexter suddenly feels “[f]or the first time in his life…like getting very drunk.” The destruction of his illusion of Judy, whom he saw as an emblem of great beauty and a representation of the rarefied social world that he had strived to join, results in the evaporation of his winter dream. He watches the sun set and, with the loss of the day, feels the loss of his youthful ideals, which no longer seem to matter.