The story begins sometime in the 16th century. Orlando, the focus of the supposed biography (which is actually a work of complete fiction), is introduced as a sixteen-year-old boy playing with "the head of a Moor" (13) that one of his noble ancestors brought home from Africa. The biographer uses this scene to describe first Orlando's family's wealth and status, and then Orlando's physical appearance, which is very youthful and attractive. Orlando is also a passionate writer, as evidenced by his sitting down with a writing book and promptly "cover[ing] ten pages and more with poetry" (15). He particularly likes to write about nature, but he finds that when he actually looks at nature while writing, it hinders him. He stops writing and ventures out onto his family's property, which is expansive, avoiding people and seeking a place in nature to be alone. He mounts a hill where he can see up to forty English counties when the weather is clear, and he describes the buildings and natural features that he sees in every direction. He flings himself down near an oak tree and relaxes for an hour until he hears a trumpet sound, signaling that Queen Elizabeth has arrived.
Orlando runs back to his home, washes and dresses himself quickly, and makes his way to the banquet hall. On his way, he stops suddenly when he sees a poor servant sitting at a table, deep in thought while writing poetry. Orlando is transfixed by this image, but he runs away when the man looks up. Orlando gets to the banqueting hall and offers a bowl of rose water to the Queen to wash her hands. He keeps his head down, only seeing her old, ringed hand. The Queen is charmed by Orlando's innocent manner and boyish attractiveness, and that night she signs a document inviting Orlando to attend her at Whitehall in two years' time.
When Orlando arrives at Whitehall, she greets him as "My innocent" (22) and ogles his shapely legs. She names him her Treasurer and Steward, gives him chains of office, and makes him the order of the Garter. From then on, he accompanies her closely wherever she goes, and it is implied that she is physically attracted to him as well. She continues to lavish titles and property upon him, making him the legal inheritor of many things after she dies. However, when she sees Orlando kissing a girl one day, she becomes enraged, breaking a mirror and moaning about it until her death. The biographer blames Orlando's action on the time period, saying that there was a climate of passion and that Orlando simply "did but as nature bade him to do" (25). The biographer notes that the girl could have been noble or low born, since Orlando's romantic taste was broad, perhaps because a certain percent of his lineage is from the lower class. The biographer focuses on this theme for a few pages, telling the specific story of Orlando being caught by the Earl of Cumberland with a girl named Sukey who worked on a ship.
After a while, Orlando tires of spending time with low-class people and returns to the Court of King James (who succeeded Queen Elizabeth). King James welcomes Orlando back happily since, as the biographer puts it, "He was young, he was rich, he was handsome" (28). Many noble ladies quickly become interested in marrying Orlando; the three who were considered the best contenders were Clorinda, Favilla, and Euphrosyne. Orlando treats with all of them, and he is especially serious about Euphrosyne, to the extent that Orlando and Euphrosyne's lawyers begin to draw up documents securing their marriage. However, while this was happening, the Great Frost occurs.
The Great Frost is an extremely severe winter that results in animals and even people freezing to death. While the people on the English countryside are negatively affected, King James takes the opportunity of a great river freezing over to have a brilliant carnival on top of the frozen river for the nobles and common people of London. Decorations, drinking booths, and colorful bonfires are set up, and nobles enjoy meeting with one another in a special area roped off from the public. The ice is frozen so completely that it is safe for everyone to walk around and celebrate, and it is so clear that one can see animals, a sunken boat, and a woman with a basket of apples, all frozen beneath the surface.
While Orlando is dancing one night (poorly, because he was a clumsy boy), he sees someone come out from the pavilion of the Muscovite Embassy and begin ice skating. He can't tell whether it is a boy or a girl because of their Russian style of dress, and he decides that it must be a boy because of the power with which the person skates. Orlando is distressed because he finds the person so seductive and yet "the person was of his own sex, and thus all embraces were out of the question" (33). However, when the person nears Orlando to curtsy for the King, Orlando realizes that it is a girl. He finds out that the girl's name is Princess Marousha Stanilovska Dagmar Natasha Iliana Romanovitch, though he will later call her by her nickname, Sasha.
None of the Russians in England speak English, which allows Sasha and Orlando to become acquainted: Sasha attempts to speak French with the young lords sitting by her at dinner one night and finds that only Orlando is able to converse with her. She speaks freely and happily to Orlando about the carnival and her complaints about the English, and Orlando quickly falls passionately in love with her. The intimacy between the two grows over the following days, which becomes a scandal of the court because of Orlando's engagement to Euphrosyne.
Everyone, including Euphrosyne, notices that Orlando is paying Sasha too much attention for it to be merely civil grace; they see, too, that he has suddenly transformed from a clumsy boy into a graceful nobleman. Not only this, but Orlando and Sasha begin to disappear together into places in the city and country occupied by common people. Orlando and Sasha go to the country for entire days and make love in the snow, wrapped in a fur cloak. When their passion dies down, Orlando praises everything about her and then they talk about everything, spanning topics large and small. Sometimes Orlando falls into a state of melancholy and speaks of gloom and death, which Sasha sees as childish. Orlando sometimes thinks that Sasha is hiding things from him, since, after all their talk, he still doesn't know much about her family and lineage; he becomes so enraged at Sasha that she doesn't know how to calm him down.
One day, Orlando and Sasha skate far away into the country and find a Russian ship partially frozen in the water. They venture onto the boat and find a young man who speaks Russian. He tells Sasha that he can help her find something she wants from the boat, and Orlando waits for them on the deck. He waits calmly for over an hour and then suddenly realizes how long it has been. He goes down into the hold of the ship and sees Sasha and the man embracing. Orlando cries out in anguish and then faints; Sasha and the man lay him on the floor and give him brandy to revive him.
When Orlando wakes up, Sasha speaks to him lovingly and convinces him that he didn't see what he thought. Orlando goes back and forth, believing her and then succumbing to doubt and rage once again, but eventually they leave together. On their way back to London, Sasha is even nicer to Orlando, praising him and telling him more about her life in Russia. As they approach the Royal enclosure, they decide to stay in the area of the common people for a while longer; they witness a production of a play, likely Othello, and Orlando briefly imagines himself suffocating Sasha as occurs in the play. Looking at the sky, he sees that it is pitch black, and in a fit of passion he whispers the secret phrase that he and Sasha had come up with to signal that they would meet up at midnight and run away together.
Orlando goes to their designated meeting place, an inn near Blackfriars, early. He waits for midnight, pacing around in nervousness and overanalyzing every sound. He is suddenly struck by a blow on his cheek and then realizes that it came from a drop of water. A downpour of rain begins, but still Orlando believes that Sasha will come. Orlando is horrified when the first strokes of midnight sound from the clock tower, but he keeps faith that Sasha will arrive at exactly midnight, the sixth stroke. When the twelfth stroke sounds, Orlando cannot lie to himself anymore. He stands in the downpour until two in the morning and then mounts his horse and gallops away. He rides until dawn, reaching the banks of the Thames off Wapping, and when the sun rises he sees that the river has melted into chunks of ice. The river flows rapidly and people are trapped on the icebergs and swept away by the current. Orlando watches in amazement for a while and then gallops toward the sea to examine the ships of the ambassadors. He sees all of them but the Russian's, and then, squinting out to sea, sees them sailing away. The chapter ends with Orlando jumping into the water up to his knees and hurling useless insults at the ship.
While Orlando does not transform from a man to a woman until Chapter III, Woolf hints at the fluidity of Orlando's gender and sexuality from the beginning of the book. Perhaps the best instance of this foreshadowing is Orlando's attraction and confusion upon seeing Sasha for the first time. Woolf writes, " A figure, which, whether boy's or woman's, for the loose tunic and trousers of the Russian fashion served to disguise the sex, filled him with the highest curiosity...Orlando was ready to tear his hair with vexation that the person was of his own sex, and thus all embraces were out of the question" (33). Orlando is attracted to the person regardless of sex, so his vexation clearly comes from the societal norms that would keep two people of the same sex from becoming intimate. Woolf also hints in this quote at the interplay of gender and clothing that Orlando will come to recognize and criticize later in the novel.
Besides being attracted to people regardless of gender, Orlando also transgresses 16th-century social norms by pursuing women regardless of their social class. The narrator writes that Orlando believes "the cheek of an innkeeper's daughter seemed fresher and the wit of a gamekeeper's niece seemed quicker than those of the ladies at Court" (26). This is something that never changes for Orlando, regardless of gender and age; he will later marry both a dancer and a sailor and refuse the advances of many high-class suitors. This facet of Orlando's personality may go along with his love of nature, dogs, and poetry in the sense that he finds them things that are honest and without social pretension.
Readers may find it odd that Woolf included some quotes in French in Chapter I without including a translation either in the text itself or in a footnote. For many centuries, due to the high costs of printing and buying books, only the highly educated read novels. Because these same readers would likely have studied French, many authors did not translate the French in their novels. The inclusion of French in such novels served to differentiate the characters by education and class and, as in Orlando, to create situations in which characters can carry on a conversation that other characters can not understand. Woolf includes quotes from Sasha that are not translated into English, but later, when Sasha and Orlando are conversing at dinner and throughout their relationship, the narration switches to an English translation of what is being said. This communicates the high education and sophistication of both characters and creates a means for them to connect over a similarity.
For today's readers, who may not be educated in French due to the rise of other global languages, a rough translation of Sasha's comments is beneficial to understanding the girl's character. When speaking to the Lord and Earl seated to her right and left at dinner, she first says "Je crois avoir fait la connaissance d’un gentilhomme qui vous était apparenté en Pologne l’été dernier" (35). This translates to "I think I met a gentleman who is related to you in Poland last summer." Next she says, "La beauté des dames de la cour d’Angleterre me met dans le ravissement. On ne peut voir une dame plus gracieuse que votre reine, ni une coiffure plus belle que la sienne" (35), meaning "The beauty of the ladies of the court of England puts me in rapture. You can not see a lady more graceful than your queen, nor a hairstyle more beautiful than hers." These quotes show that Sasha has been trained to have the manners of a high born woman, but also that she will not bother to switch to English when her speaking partners clearly do not understand. By leaving these quotes untranslated, Woolf allows a reader uneducated in French to have a parallel experience to the Lord and Earl's. In contrast, a reader who has studied French would have a parallel experience to Orlando's: he is able to overhear and understand Sasha's attempts at well-mannered small talk.
The fair held in London during the Great Frost described in Orlando is not entirely fictional. The Thames froze completely twice in the 15th century, five times in the 16th century, and ten times in the 17th century, and fairs were often held to celebrate the freezing. However, one winter in particular, the winter of 1683-1684, was named the Great Frost. This historical event helps the reader locate Orlando in time, and it provides the first sign that Orlando's life will not line up to a typical human lifespan. It is later noted in the book that Orlando began writing his work "The Oak Tree" in 1586, which means that Orlando has lived for at least 100 years at the time that he meets Sasha. By the end of the book, Orlando will have lived over 300 years, but physically will only be middle-aged. Since Orlando's age will not reflect the passing of time, famous events and time markers such as the existence of certain buildings or technological inventions can help a reader establish historical context.