Orlando swings his sword at the “Pagan” head of a Moor hanging from the rafters of his father’s expansive English mansion. Orlando’s father—or perhaps grandfather—took the head while riding “in the barbarous fields of Africa,” and Orlando is eager to follow in their footsteps. For now, however, he is just 16, and terribly late to meet the Queen. A loud whistle announces Queen Elizabeth I’s arrival, and Orlando rushes to change his clothes. He runs to the reception line and bows down before the Queen with a bowl of rose water just in time for her “nervous, crabbed, [and] sickly” hands to accept his offering. Orlando never looks up, but the Queen falls in love with the top of his head and considers him “the very image of a noble gentleman.” Two years later, the Queen invites Orlando to join her court at Whitehall and makes him her “Treasurer and Steward.” Orlando lives a lavish life surrounded by many beautiful and adoring women, but his first love is poetry. He has “the wildest, most absurd, extravagant ideas about poets and poetry,” and he is a prolific writer of prose and poetry himself, all “very long” and “abstract.” Orlando is soon betrothed to Lady Margaret—or Euphrosyne, as she is known “in his sonnets”—but he quickly falls in love with Sasha, a Muscovite princess, whom he meets during the festival of the Great Frost. They make plans to run away together, but when Orlando goes to meet her just as the Thames River begins to melt, he sees the ship of the Russian Ambassador moving out to sea, and he knows Sasha is onboard.
After Sasha’s deception, Orlando is crushed, and since he had made no attempt to hide his feelings for Sasha from Euphrosyne, he is a complete disgrace at court. Depressed and dejected, Orlando fails to wake at his usual time on Saturday, the 18th of June, and sleeps without “any sign of life” for a week. On the seventh day, Orlando wakes at his usual time with an “imperfect recollection of his past life.” He is examined by a whole slew of doctors who prescribe a myriad of treatments, including rest and starvation, and ultimately agree that Orlando has indeed been asleep for a week. As a biographer, the narrator acknowledges that Orlando’s case is quite unbelievable, but it is their duty “to state the facts as far as they are known, and so let the reader make of them what he may.”
Increasingly depressed and obsessed with death, Orlando turns to the therapeutic effects of writing, and works on his poem, “The Oak Tree,” which he has been writing for several years. He also writes a friend, an acquaintance of several poets, and asks him to invite Nicolas Greene, “a very famous writer,” to Orlando’s home for a visit. Greene accepts, and he tells Orlando over dinner that poetry in England is “dead.” Shakespeare and Marlowe only write for money, Greene says, and have no “Glawr,” or “divine ambition.” The Greeks were great, Greene claims, not the Elizabethans. After Greene’s visit with Orlando, Greene returns home and writes a satirical “roast” of Orlando, in which he negatively reviews Orlando’s original play, the Death of Hercules, calling it “wordy and bombastic in the extreme.” Crushed again, Orlando returns to the comfort of “The Oak Tree,” and later meets the Archduchess Harriet Griselda. However, Orlando realizes that his feelings for the Archduchess are “Lust the vulture, not Love, the Bird of Paradise,” so he asks King Charles to send him as an Ambassador to Constantinople.
During his time in Constantinople, Orlando fulfills his duties as Ambassador with “admiration,” and he is even awarded a Dukedom. But, the narrator claims, a great fire broke out during the Revolution, and most official records were lost. “We have done our best to piece out a meagre summary from the charred fragments that remain,” the narrator says, “but often it has been necessary to speculate, to surmise, and even to make use of the imagination.” On the day Sir Adrian Scrope delivers Orlando’s patent of nobility, Orlando throws an extravagant ball, during which, according to rumor, “some kind of miracle” is going to be performed. When Orlando accepts his patent and Dukedom but no miracle occurs, the crowd of people begins to riot, and Sir Adrian and “a squad of British bluejackets” must hold them back.
Later that night, a figure is seen embracing a “woman of the peasant class” on Orlando’s balcony, and the next morning, Orlando again fails to wake at his usual time. Doctors are called and Orlando is examined. His room is quite trashed, and there are several papers thrown about, including some poetry about oak trees and a marriage deed issued to Orlando and a “gipsy” dancer named Rosita Pepita. He again sleeps for a week, and when he wakes on the seventh day, Orlando is a woman. Orlando’s change has occurred so “painlessly and completely” that she is not in the least bit surprised by it. “The change of sex,” the narrator declares, “though it altered [Orlando’s] future, did nothing whatever to alter [Orlando’s] identity.” Orlando immediately dresses and leaves the house, heading straight to the lands of the “gipsies.” She lives with them for some time, but they have no ink or paper, so Orlando heads back to England.
Aboard the ship to England, Orlando begins to understand “the penalties and the privileges of her position.” She is much the same person she has always been, but the addition of a petticoat has altered things significantly. Living as a woman involves “the most tedious discipline,” and Orlando is expected to dress, look, and smell impeccably. Orlando isn’t, of course, naturally this way, and it takes several hours out of her day to accomplish. Orlando continues writing her poem, “The Oak Tree,” and she immerses herself in London society. At a party given by Lady R., whose drawing room is said to be the wellspring of intellect and genius, Orlando meets Alexander Pope, a famous poet of the 18th century, and asks him to come home with her. He does, and Orlando’s home consequently becomes the favorite meeting place of famous poets. Orlando decides to keep a book to record all the witty things they say, but the book remains empty, and she quietly works on her poem. Before Orlando knows it, the 18th century ends, and the 19th century begins.
With the new century comes a new queen and a new climate, and a “dampness” settles over England. Orlando is completely at odds with the new era and finds it impossible to write. A “tingling and vibration” consumes her body, originating in “the second finger of her left hand,” and Orlando decides she must get married, “in the spirit of the age,” if she is ever to finish her poem. Orlando takes a walk in the park, and after she trips and breaks her ankle, she meets Marmaduke Bonthrop Shelmerdine. Orlando and Shel are engaged in minutes, and the next day, Shel looks to Orlando suddenly. “Orlando, you’re a man!” Shel exclaims. “Shel, you’re a woman!” Orlando responds. They are married on Orlando’s estate, but no one hears the word “Obey” spoken before the passing of the rings.
Shel is a sailor and is frequently gone around the Cape Horn, and Orlando is left alone to put the finishing touches on “The Oak Tree.” She has, after all, been writing it for more than 300 years now. “Done!” Orlando yells, stepping away from the poem for the last time. She knows it must be read, and she immediately heads into London. In the city, Orlando runs into Nicolas Greene, who is now “the most influential critic of the Victorian age.” After Greene laments the state of poetry in England—Shakespeare and Marlowe, “those were the giants,” he says—Orlando’s dress pops open, and “The Oak Tree” falls from her bosom. Greene reads the poem immediately and, claiming it reminiscent of the great Elizabethans, insists that it must be published. After Orlando and Greene part, Orlando rushes to wire Shel a telegram and tell him the great news about her poem, and then she wanders into a bookstore. She buys several of Greene’s critical works, tells the shopkeeper to “send her everything of any importance,” and begins to read. She learns that critics expect writers to “always write like someone else,” and that all of Victorian literature can be either written “out in sixty volumes octavo,” or squeezed “into six lines the length of this one.” After coming to this conclusion, Orlando looks out the window for a long time, and on “March the 20th, at three o’clock in the morning,” the midwife hands Orlando a baby. “It’s a very fine boy, M’Lady,” the midwife says.
Orlando again stands at the window. “But let the reader take courage,” the narrator says, “nothing of the same sort is going to happen today, which is not, by any means, the same day.” The world outside is changing. Light floods houses with the flip of a switch, and water is hot in seconds. A nearby clock strikes. It is 10 a.m. on October 11, 1928, and it is “the present moment.” Orlando stops and grabs at her heart. There is not a more “terrifying revelation,” the narrator notes, “than that it is the present moment.”
Orlando hops in her car and drives. She has some shopping to do in town, but she leaves without most of her list. “This is the oncome of middle age,” Orlando says. “How strange it is!” She drives until she comes to a cottage and farm and gets out of the car. “Orlando?” Orlando cries out, “Orlando?” When no one answers, Orlando gets back in her car and drives home. Walking through the many empty rooms of her sprawling mansion, Orlando thinks of the numerous parties and people who graced the rooms over the past centuries and feels a sort of depressed nostalgia.
She walks out to the garden and down a remote path to an old oak tree. Orlando places her poem, “The Oak Tree,” at the base of the tree and looks to the sky. She can see an airplane flying overhead, and she knows that Shel is onboard. “Here, Shel, here!” Orlando yells to the sky. Shel jumps from the airplane, and as he does, “a single wild bird” flies up over his head. “It is the goose!” Orlando yells. “The wild goose...” and then “the twelfth stroke of midnight” strikes on “Thursday, the eleventh of October, Nineteen Hundred and Twenty-eight.”