The nineteenth century begins with a cloud hanging over all of London. None of the colors are as bright and dampness seeps into every home. The dampness strikes within, as men feel a chill in their hearts, and love and warmth are "swaddled in fine phrases." The sexes grow farther apart. Ivy and gardens are becoming overgrown; the narrator describes the suffocation of excess growth. Orlando looks out the window of her carriage and sees a monument of assorted rubbish held up by the figure of a woman half-clothed and of a man fully- dressed. The monument is in the park where the figure of Queen Victoria now stands. Orlando concludes her eyes must be playing a trick on her.
She goes to her home in the country and feels very cold there. The walls have grown so much with ivy that very little sunlight is getting through the windows. Her housekeeper tells her that Queen Victoria is wearing a crinoline, which means she is trying to hide the fact that she is pregnant. The narrator comments that all women in this period must, out of modesty, try to hide their condition until it becomes too late. Orlando thinks about how she must soon go out to buy her own crinoline and she blushes. She takes the manuscript of "The Oak Tree" out of her bosom which she began in 1586, almost 300 years ago. She reflects on how the poem changes with her maturation, sometimes gloomy, sometimes romantic, sometimes satirical, but she sees that beneath her changes, she has always been the same person.
Orlando tries to write more of her poem and she finds that her hand is controlled from something external. Her hand moves and poetry flows from her pen without her giving it a thought. Orlando is frightened and feels a tingling in the finger on which she wears Queen Elizabeth's ring. She looks around and sees that everyone seems to be wearing wedding rings. People everywhere seem not to be moved by passion, but are eternally linked together in bands of gold. This situation seems unnatural and repugnant to Orlando. Yet she is unable to write poetry. She is thirty-two years old now, and she feels that this century is not right for her; it is 'antipathetic' to her nature. Nevertheless, she decides she must "yield to the spirit of the age" and take a husband.
Orlando wonders whom she can marry. The Archduke Harry has long since married someone else and all her old friends are gone. She feels that everyone is married except herself, and she longs for someone to lean upon. She goes for a walk alone and feels nervous. She finds a feather, puts it in her hat, and starts following a trail of feathers. Immediately, she grows more content. She follows the feathers to a lake and falls and twists her ankle, but she is happy. She whispers, "I have found my mate. It is the moor. I am nature's bride." She lies down on the ground and thinks she is dying. Soon she hears a horse galloping toward her.
The man on the horse is Marmaduke Bonthrop Shelmerdine, Esquire. He asks her if she is all right, and a few minutes later they become engaged to be married. The narrator notes that the two know everything of importance about each other within two minutes. Shel takes her to have breakfast and she learns that he is a seaman and adventurer who sails around Cape Horn. When Orlando exclaims that she loves him, they have a strange realization at the same time. Shel realizes Orlando is a man, and Orlando realizes Shel is a woman. Yet Orlando thanks Shel sincerely, saying she has never felt more like a real woman.
After a few days of Shel and Orlando being together a message comes from the Queen. The letter says that all of Orlando's lawsuits have been settled: the Turkish marriage is annulled, the children pronounced illegitimate, and Orlando's sex is declared to be female beyond a doubt. She is now in full claim of all of her titles and property again, but the lawsuits were so expensive that Orlando is actually quite poor. The town rejoices when they hear the news that Orlando's suits are settled, and she once again receives many invitations from important English lords and ladies. Instead, Orlando chooses to spend her time alone with Shel.
Shel cannot believe that Orlando is a woman because she is "as tolerant and free-spoken as a man" and Orlando cannot believe that Shel is a man because "he is as strange and subtle as a woman." They get along quite well together, understanding each other perfectly. She loves hearing of his stories of Cape Horn. One day in the forest, leaves start to drop and Orlando feels a chill. Shel realizes that the wind has changed direction and it is time for him to sail again. Shel and Orlando run to the house, and a servant quickly marries them in a rushed ceremony. They cannot hear over the wind, and the words just as well may be "jaws of death" as "honor and obey." Shel mounts a horse and rides away to his ship. Orlando goes inside, a ring on her finger.
Much of Orlando deals with a protagonist who feels the need to conform to the image and morals of those who surround him. Nowhere is this process more difficult for Orlando than in the nineteenth century. The imagery that the narrator employs to describe this period mirrors the emotions and frustrations of her subject. She writes that a dark cloud hangs over all London; ivy and vegetation is everywhere overgrown and no sunlight can get in. Children and vegetables are produced in abundance, and in everyone there is a chill; they are cold both inside and out. Such imagery conveys the suffocation that Orlando feels from the oppressive "spirit of the age." Here Woolf alludes to the Victorian period, known for industrial abundance and strict, moral patterns of behavior. Orlando looks around and sees that everyone is married; people seem to have been born by couples. She feels a literal tingling in her left finger, which would carry a wedding ring. Orlando knows that to successfully exist in this age, she must find a husband.
Chapter Five would have been especially meaningful for the Bloomsbury Group, as many of its members opposed Victorian morality. They resented being told the correct way to act and the most moral way to live one's life. Such rules were suffocating to them. For Orlando, who is now a woman, the nineteenth century, with all its limitations on female activity, is most difficult. She cannot run as well in her layers of skirts and petticoats. She is scorned for walking unaccompanied in public. In short, to exist as any sort of public figure, she needed a husband. The feminist in Orlando (and in Woolf) rejects such dependence on men. Orlando decides that nature will be her husband.
Woolf parodies gothic romances in the passages with Orlando and Shelmerdine. The scene in which Orlando runs across the land, calling herself the bride of the "moor," clearly pokes fun at Emily Bronte's Wuthering Heights, which romanticizes the wild nature of the landscape. It is comic that Shel sweeps Orlando off her feet and that within two minutes the pair know everything there is to know about one another. Woolf seems skeptical that any love like this could ever be real. It is more likely that such a 'love' is the result of an age with glorifies and demands it.
However, the relationship with Shel is the nearest that Orlando comes to finding love. They are so attracted to each other because they see the best qualities of their gender in the other. Shel is "strange and subtle as a woman," while Orlando is "tolerant and free-spoken as a man." Despite the dictates of their age, they do not conform to such clearly divided gender roles. They are complex individuals, and though their behavior may be influenced by the Victorian spirit, their selves reveal the complexities that belie clearly marked rules.