Osha is a woman of the Free Folk (or "wildling"), now in service to House Stark of Winterfell. Osha is currently escorting Rickon Stark to Last Hearth to seek refuge with House Umber.
Osha is a wildling spearwife, one of the "Free Folk" who live north of the Wall. Like other wildlings, she worships the Old Gods of the Forest. Due to the rising threat of the White Walkers and their undead wights, Osha fled south of the Wall with a group of other wildlings, hoping to go "as far south as south goes". They bypassed the wall by taking a boat across the Bay of Seals, to the east of the Wall.
Osha joined Stiv and Wallen to form a band of wildlings. They fled south and abandoned their service to Mance Rayder. The group crossed the Wall and travelled into the Wolfswood north of Winterfell. They chanced upon Bran Stark and try to steal his horse. Robb Stark intervened, killing Wallen and taking Osha prisoner. Stiv held Bran at knifepoint, but was shot in the back by Theon Greyjoy. Osha surrendered to Robb and was taken to Winterfell.
Osha was put to work as a servant. Theon is irritated when she refused to call him "My lord," especially when she correctly pointed out that his father is still alive so he is not entitled to the honorific title yet. Maester Luwin sent Theon away and asks Osha why she was south of the Wall. She replied that there were things sleeping under the ice which are not sleeping any more. Luwin is skeptical of her claims.
Osha goes to Winterfell's godswood to pray to the Old Gods of the Forest, and found Bran there. She tells him that north of the Wall, the old gods are the only gods. She also says that Robb was leading his army in the wrong direction. The true enemy lay to the north, beyond the Wall, not the south. When Hodor passed by naked, Osha remarks he must have giants' blood in him, and tells Bran that giants - and worse - exist north of the Wall.
Bran dreamt that he saw his father Ned in the catacombs of Winterfell. Osha carried Bran into the tombs to check. Once inside they are surprised by Shaggydog and found Rickon there too: he had experienced the same dream as well. When they emerge from the tomb Luwin told the boys that their father has been killed.
Osha continued to discuss Bran Stark's strange dreams with him. He denied having had any more but nevertheless insists on being taken to the pool in the Godswood. She correctly predicted that the Red Comet signified the return of Dragons to the world. Bran told Osha that he has dreamt of seeing a Three-eyed raven but she offered no explanation. He also confided that he had experienced a dream about the sea coming to Winterfell and drowning Ser Rodrik Cassel. Ser Rodrik left Winterfell to relieve a siege of nearby Torrhen's Square by unknown forces.
The siege was in reality a feint orchestrated by Theon Greyjoy to draw away Winterfell's defenders. Theon infiltrated and seized the castle forcing Bran to surrender and yield Winterfell to him. Later, Osha offered to fight for Theon but he refused, suspecting treachery. Osha was also present with Bran and Rickon when Theon personally executed Ser Rodrik in public. She comforted the boys and told Bran that his dream has come true.
Later that night, Osha seduced Theon, claiming that she wanted her freedom. While he sleeps she freed Bran, Rickon, and Hodor escaped with them. She murdered the guard Drennan as they make their exit. They walked to a shepherd's farm in the Stark lands. They consider approaching the farmer for food. Theon tracked them to the farm using hounds and then loses their scent. He returns to Winterfell with the charred corpses of two boys, claiming they are Bran and Rickon. He made no mention of Osha and Hodor. The escapees actually doubled back, using a stream to mask their scent and were hiding under Theon's nose in the crypts of Winterfell. Luwin spotted Osha smuggling bread into the catacombs and followed her. She explained their escape and Luwin told her that the bodies must be those of the orphan farmhands. She promised not to tell the boys, agreeing that they have suffered enough.
Later, Roose Bolton's bastard son Ramsay Bolton launched a siege of Winterfell. Theon was betrayed by his own men who turned him in return for safe passage to the Iron Islands. However, Ramsay reneged on his promise and had them flayed alive. He then took Theon prisoner and sacked Winterfell, killing many of its inhabitants and sacking much of the castle. Since they were hiding under the catacombs, Osha, Bran, Rickon and Hodor managed to evade capture. Before leaving Winterfell for the north, Osha encountered a dying Maester Luwin and used a dagger upon his request to give him the "gift of mercy". Luwin instructed Osha to escort Bran and Rickon to the Wall so that they can find their half-brother, Jon Snow. Osha agreed and left Winterfell with Hodor, Bran, Rickon and their direwolves.
Fleeing from Winterfell, Bran's group encountered Jojen and Meera Reed. Jojen approaches their camp unarmed but Osha sneaked up on him with a sharpened stake. However, she was surprised by his sister Meera who had snuck up behind her, and held a knife to her throat. Bran insisted that everyone calm down. Jojen claimed that he received greensight visions which told him where to find Bran, and that he would need their help. The group continued to travel north to Castle Black, as Maester Luwin instructed, hopefully to find Jon Snow
Fueled by the long animosity of the Northerners and Free Folk towards each other, Osha and Meera get into an argument about which of them can skin a rabbit better, which turns to who is doing the hunting, to arguing about who trusts who. Bran again tells them to make peace. Jojen then starts shaking violently in his sleep, and Meera holds down his tongue with a cord so he doesn't bite himself. She explains that the visions take their toll. Osha dislikes this, thinking it is black magic. On waking, Jojen says that he saw Jon Snow - and that he isn't at Castle Black, but on the north side of the Wall, and surrounded by enemies.
Osha's pent-up frustration comes to a head, and she says she doesn't want Jojen influencing Bran with black magic anymore. Bran explains that because Jojen's vision said Jon Snow isn't even at Castle Black, they shouldn't head there anymore. Instead, Bran and Jojen believe that the Three-eyed raven in his dreams is leading him Beyond the Wall, so they should head directly north to the structure, instead of turning to head to Castle Black. Bran says that he believes that maybe the gods meant for him to find the three-eyed raven, meant for him to have these visions, and ultimately, his fall from the tower that crippled him happened for a reason. Osha is outraged and says she will never go back north of he Wall again.
Osha then explained to them the reason she fled south of the Wall. She once had a husband named Bruni, a good man who loved her. One day he disappeared, and everyone said he'd simply left her, but she knew him better than that. One night he did return to their hut - as an undead wight, with skin pale as a dead man's and his eyes bluer than clear sky. Bruni began to choke her. Somehow she managed to get hold of a knife, and rammed it deep into his heart, but he didn't even seem to notice. Osha ultimately managed to get away by burning down their hut with Bruni inside it. She didn't ask the gods for that, she says, but their message was clear: north of the Wall is no place for living men to be anymore.
Eventually, Osha and her masters reached The Gift, a region south of the Wall which was considered to be beyond the borders of the Seven Kingdoms. The Gift had been gifted to the Night's Watch thousands of years ago by Brandon the Builder, from which the Watch draws support for its material needs. While the region was fertile, it was uninhabited due to frequent Wildling attacks which had forced the Smallfolk to migrate south over the centuries. Bran's discussion of this history and Rickon's remarks about Wildlings drinking blood caused Osha some discomfort since she was a Free Folk. That evening, the party took shelter at an abandoned mill to escape a thunderstorm. Later, the group observed a band of Wildlings chasing down a lone Northman. During the ensuing incident, Bran used his Warg powers to Warg through Summer and Shaggydog and fight off the Wildlings. This party of Wildlings included Rickon’s half-brother Jon Snow, who earlier had been taken captive by the Free Folk. Using his Warg abilities, Bran helped Snow to escape from his captors and return to the Night's Watch.
Later that night, Bran arranged for Osha to bring Rickon to the holdfast of Greatjon Umber, the Lord of Last Hearth and the head of House Umber. Lord Umber was a loyal ally of the Starks. While Rickon was upset to be separated from his brother, he realized this was for his own good and cooperated with Bran and Osha. This arrangement also suited Osha because she was unwilling to travel with Bran and company due to the threat posed by the White Walkers. During their journey to Greatjon Umber, Rickon and Osha were accompanied by the former’s direwolf Shaggydog. Meanwhile, Bran, Hodor, Jojen Reed, and Meera Reed head beyond the Wall.
Osha and Rickon are betrayed by the Umbers when the new Lord of Last Hearth, Smalljon Umber, wants to protect his lands from the wildlings that have been given safe passage through the Wall by Jon Snow. Lord Umber still makes it clear that he hates the Boltons and that he will not pledge allegiance to them. However, to gain Ramsay Bolton's support, he offers him Osha and Rickon Stark. At first, Ramsay does not wholly believe the boy to be truly Rickon. When the Smalljon presents him with the head of Rickon's direwolf, Shaggydog, Ramsay sarcastically welcomes Rickon home.
Ramsay later has Osha brought to him, and asks her about her involvement with House Stark. Osha pretends to have been a slave and says that she carried around Rickon to find a buyer for him. She also tries to seduce Ramsay, but it was only a ruse to get him distracted and kill him with the knife that was in the table next to him. As Osha lies on his lap, Ramsay reveals that Theon had told him how she helped the Stark boys escape. Osha rushes for the knife, but Ramsay takes another one out from his holster and stabs her in the neck. Osha falls to the floor and bleeds to death as Ramsay cleans the blade and watches in amusement, returning to peeling his apple with the same knife used to kill her.
A wildling who was captured after treatening Bran, Osha joined the Stark household as a servant. Along with Hodor, she traveled north with Bran, Rickon and the Reeds until Bran sent her to escort Rickon to Last Hearth. The new lord of Last Hearth, Smalljon Umber, delivered them to Ramsay Bolton. When Osha tried to seduce Ramsay, he killed her, aware it was a ploy to escape.