Linda escapes from Mr. Flint's plantation and heads for her grandmother's house, where she persuades Sally, "a faithful friend," to help her reach the home of another friend, who hides her in a closet. After hiding at her friend's home for a week, Linda's pursuers come into close vicinity. She flees, terrified of being discovered, and hides for two hours in some nearby bushes, where she is bitten by a poisonous reptile. In excruciating pain, she returns to her friend's house, where she is treated with homemade medicine.
Meanwhile, Linda has contacted some of her relatives, who advise her to return to her master, beg his forgiveness, and accept her punishment. But when her friend informs her family of the pain and suffering Linda has endured in her struggle to remain free, they stop trying to convince her to go back. Desperate to help Linda, her grandmother enlists the aid of a woman she has known since childhood, who offers to help her escape and agrees to let her stay at her home until she can get to the Free States. The woman arranges for her cook, Betty, to meet Linda at a designated place and bring her to her home. When Linda receives the message to meet "a friend" at a secret location, she is surprised to discover that the "friend" is Betty. Betty escorts her back to her mistresses' house, brings her supper, and shows her to her new hiding place: an old storage room.
Linda learns that Dr. Flint has had her brother, William, her children, and her aunt (who has served the Flint family for over 20 years) arrested, hoping to force them into revealing her hiding place. Devastated that her actions are causing her family so much suffering, Linda considers turning herself in, until she receives a note from her brother, begging her to stay put and convincing her that turning herself in now would only serve to further endanger her family.
After a month, Linda's aunt is released and her daughter, Ellen, is taken to Dr. Flint's home, where she is treated for the after-effects of measles. That night, Dr. Flint, on his way back from seeing a patient, passes by Aunt Martha's cabin. Noticing that her light is still on and suspecting that Linda might be hiding at her grandmother's, he stops by to tell her that he knows where Linda is and will have her back by 12:00. He hopes that she will reveal Linda's hiding place. Alarmed, Aunt Martha and Uncle Phillip send a message to Betty's mistress, and Betty conceals her under some planks beneath the kitchen floor.
Several days later, Dr. Flint comes to the house where Linda is hiding, and Linda once again fears that she has been discovered. But after he leaves, her friend tells her that Dr. Flint — who has already posted a reward notice of $300 for Linda's capture — came to borrow $500 so that he could search for her in New York. She assures Linda that she is safe and has nothing to fear.
When Dr. Flint returns from New York, Linda's friends trick him into selling William (her brother), Ben (her son), and Ellen (her daughter) to a slave trader who represents Mr. Sands. The trader pretends to leave town with them, but then releases William and the children and allows them to go back to Aunt Martha. Linda, who is unaware of these transactions, has a vision in which she sees her children. Terrified that her children are dead, she turns to Betty, who reassures her that they are safe at home with her grandmother.
Dr. Flint has Phillip arrested on charges of aiding Linda's escape and demands $500 bail for his release. Meanwhile, the hunt for Linda continues and Betty again hides her under the kitchen floor. Just as she begins to feel safe, Jenny, another household slave, threatens to reveal Linda's hiding place. Afraid that she will be discovered, Betty's mistress contacts Phillip, who arranges for a friend to meet her. Disguised as a sailor, Linda meets Phillip's friend, Peter, who escorts her to the wharf, where Aunt Nancy's husband smuggles her aboard a ship, providing her with a temporary shelter. Later, Peter takes her to hide in Snaky Swamp, where Linda is terrified of the huge snakes. Although she is able to spend the night aboard the docked ship, Linda is forced to spend another day hiding out in the swamp. The following morning, Peter tells her that a hiding place has been secured for her. Linda, who has become severely ill from her ordeal, dons her sailor's disguise, blackens her face with charcoal, and follows Peter back to her grandmother's house.
Linda recounts the harrowing circumstances surrounding her first "flight" or escape. The motif of flight (which can refer to literal flight or escape) is prevalent in numerous works by African American authors, such as Walter White's Flight, Ralph Ellison's Flying Home, Ishmael Reed's Flight to Canada, and Toni Morrison's Song of Solomon, which is based on the myth of the flying Africans. The language of flight is common in Jacobs' narrative. For example, when she makes her initial escape, she heads toward her grandmother's house "with almost lightening speed." And as her pursuers near her hiding place in a friend's home, she says, "I flew out of the house, and concealed myself in a thicket of bushes."
Masks, disguises, and deceptions are another prominent theme throughout the narrative. For example, Linda's escape depends on her ability to trick Dr. Flint by writing him letters that her friends then postmark from New York. Note also that when Linda boards the ship, she is disguised as a sailor. Benjamin escapes by passing, or masking his true identity, and Linda's son later follows in his great-uncle's footsteps. Linda also focuses on the fact that slavery deprives people of their ability to trust others. And for enslaved blacks, masking one's true feelings and identity was often crucial for survival.
In addition to masks and disguises, snakes are another key symbol in these chapters. In Chapter 18, Linda is bitten by a poisonous reptile, probably a snake, while hiding in the bushes from her pursuers. And in Chapter 20, Linda hides in Snaky Swamp, where she and Peter are surrounded by "snake after snake crawling round us." Because snakes can shed their skin, they often symbolize rebirth or renewal. Recall, however, that in the biblical story of the Garden of Eden, a snake tempted Eve and as a result, Adam and Eve were evicted from the Garden. Therefore, snakes can symbolize both birth and death. Although Linda is terrified of snakes, she prefers hiding out in Snaky Swamp over returning to her master: "even those large, venomous snakes were less dreadful to my imagination than the white men in that community called civilized." Snaky Swamp symbolizes the death of her old life and the perilous beginnings of her new life as a fugitive.