In 1948, Frank Wheeler (DiCaprio) meets April (Winslet) at a party. He is a longshoreman, hoping to be a cashier; she wants to be an actress. Frank later secures a sales position with Knox Machines, for which his father worked for 20 years, and he and April marry. The Wheelers move to 115 Revolutionary Road in suburban Connecticut when April becomes pregnant.
The couple becomes close friends with their realtor Helen Givings (Bates) and her husband Howard Givings (Richard Easton), and neighbor Milly Campbell (Kathryn Hahn) and her husband Shep (David Harbour). To their friends, the Wheelers are the perfect couple, but their relationship is troubled. April fails to make a career out of acting, while Frank hates the tedium of his work. Meanwhile, Helen asks the couple to meet her son, John (Shannon), who had been declared insane, to try to help better his condition. They accept.