Meanwhile Frodo and Sam are making their way across the bare hills of Emyn Muil, and the sheer walls of the ridge prevent them from descending into the plains. At last they find a place where a descent might be possible, and Frodo attempts to climb down; a terrible cry pierces the sky at that time (probably made by the winged steed of one of the Nazgul), and Frodo falls but fortunately lands on a shelf not deep below. Sam remembers the rope that the Elves of Lórien gave him and rescues Frodo with it; then they both climb down the rope and, to their surprise, manage to pull it down easily afterwards, as if it had not been fastened to anything at all. They plan to spend the night under the cliff not far from there. Then they notice Gollum, who had been following them all the time; he climbs easily, almost like a spider, but falls down in the final part of the climb. Sam attacks him, and with Frodo's help they force Gollum to promise that he would lead them to Mordor. Soon afterwards Gollum tries to escape, but they catch him and find that the elven-rope with which they wanted to tie him hurts him greatly. He swears by the Ring that he would obey them, and they untie him. A little later, when the moon has also set, they head downwards again.
The two hobbits, led by Gollum, are slowly making their way towards the Black Gates of Mordor. Since going through the open land full of orc-highways would be far too dangerous, Gollum leads them along less-known paths through the marshy lands. They cross the Dead Marshes, where many fallen warriors were buried during the war between the Last Alliance and the Dark Lord at the end of the Second age; now strange lights flicker there, and horrible dead faces can be seen under the mud. Ringwraiths often fly above them, apparently searching for the Ring and somehow sensing its presence; and the burden of the Ring seems ever greater to Frodo as they near Mordor. Within Gollum two 'personalities' are struggling for domination: the good Sméagol, and the wicked Gollum; and pressed by the mad desire for the Ring the Gollum in him seems to be winning again. Finally they reach the desolate and barren lands before Mordor, and only at Frodo's strict command is Gollum willing to guide them further.
The companions reach the Black Gate of Mordor. The Gate is guarded by the Teeth of Mordor, two tall towers erected long ago by the Men of Gondor but were later abandoned and then occupied by Sauron's forces. There are also many other battlements and huge numbers of orcs; several roads are leading to the gate, and numerous armies from the East and the South are coming into Mordor. Entering Mordor there seems absolutely impossible. At this point Gollum suggests another way: to go southwards to the ghost-city of Minas Ithil, and then up to the pass of Cirith Ungol. There the chances of not being noticed are somewhat greater, for in that direction Sauron has conquered land as far as the Anduin, and feels safer, so the place is not likely to be watched so thoroughly. Gollum claims he had escaped from Mordor along that very path, though it seems likely that this 'escape' was known and approved by the Dark Lord. Nonetheless Frodo, after some hesitation, decides to accept this plan.
Journeying south, the company reaches Ithilien, a fair country of mild climate and lush vegetation that has only been conquered by the Dark Lord recently and has not yet been desolated and defiled. Sam is becoming more and more concerned about food: their only food is lembas, which will hardly last until they reach Orodruin, and certainly not any longer. So one day as they rest in a forest, he asks Gollum to catch something edible. Gollum catches a pair of young rabbits and Sam prepares a stew. However, soon after they finish their meal, the fire starts to smoke and the two hobbits are surrounded by four soldiers of Gondor, one of them being Faramir, the Captain. Frodo explains something about his errand, and Faramir seems greatly interested in that; but at present he leaves two men to guard them, and goes away to prepare for battle: the men of Minas Tirith have come to Ithilien to attack a host of the Southrons travelling towards Mordor to join Sauron's forces. Sam sees a most amazing thing during this battle: an 'Oliphaunt', one of the great grey animals that are in Shire only known through old rhymes.
After the battle Faramir (who turns out to be Boromir's brother) returns and questions Frodo for a while; he is somewhat suspicious at first, and tells that he had seen the boat with Boromir's body float down the Anduin. At last he decides that Frodo and Sam should come with him and the host to a hidden refuge, a cave hidden behind a waterfall. Unlike Boromir, who always sought to win glory with his valour in the wars, Faramir is not so warlike and has a greater reverence for old lore and traditions (and the Elves). He talks with the two hobbits for a long time, and tells a lot about Minas Tirith and her wars, the history of Gondor, its alliance with the Rohirrim; Frodo describes the journey of the Nine Walkers, carefully avoiding the matter of the Ring. Eventually the conversation turns to the Elves and Lórien, and Sam accidentally mentions the Ring. Here Faramir proves that he is indeed true to his words, and does not attempt to take or even see the Ring.
Later that night, Gollum appears at the pool near the cave, catching fish without knowing about the hidden place. The laws of Gondor would require anyone who comes near the cave to be killed; but Faramir wakes Frodo and asks him about his opinion. Frodo explains that the creature they have seen was Gollum, and that he has guided them, and that he should not be killed. Faramir will not let Gollum wander about the area freely, and Frodo goes down and convinces Gollum to follow him. Two of the guards then catch him and take him, blindfolded and tied, to the cave. Faramir questions Gollum, and Gollum swears that he will never return to the hidden cave. Then Faramir gives Frodo permission to move through Gondor freely, and warns him, saying that Minas Morgul is an evil and dangerous place.
Faramir gives each of the hobbits a staff, as well as some provisions, and then the hobbits and Gollum depart. They travel southwards for two days and come near the road from the ruins of Osgiliath to Minas Ithil. Gollum keeps urging them to make haste, stressing the danger they are in. They turn eastwards towards the Cross-roads, the crossing of the road from Osgiliath and the north-south road. The next day the darkness starts issuing from Mordor; a great cloud covers the entire sky, and the day is as dark as a night. They reach the Cross-roads; a great stone statue of a king is standing there. Its head was apparently cut down by the servants of Sauron, and is lying on the ground near the statue; yet just before setting the sun reaches the end of the dark cloud and one of its last rays shines on the head like a crown, giving Frodo new hope.
The travellers pass the city of Minas Morgul, and Frodo feels that the Ring is drawing him towards it. They see a great army issue from the city, apparently heading towards Gondor, led by the Captain of the Ringwraiths himself. Then the hobbits and Gollum ascend a long and steep stairway, followed by another, longer but not as steep. Far above they see the pass they are heading for, and it seems to be guarded by a watchtower. They decide to rest for a while, and while Frodo and Sam are talking Gollum goes away; then they both fall asleep, and Sam wakes to see Gollum bending over Frodo. Although it seems he had no evil intentions at that moment, Sam is full of distrust. He then wakes Frodo, who offers Gollum to go freely where he will, as the hobbits could continue the way by themselves. But Gollum says they can't reach the top of the pass on their own, and all three prepare to go on.
A short time later, they reach a great mountain-wall, where the path continues through a tunnel. A terribly foul stench is coming from the it. The tunnel is very long, going ever upwards, with side passages here and there. The hobbits, walking a few steps behind Gollum, notice that the stench is becoming worse and worse, until they reach a side passage where the reek seems to be coming from. They pass it by, and the air starts to improve; but soon they come to a fork of the main tunnel. Gollum seems to have abandoned them, and they try one of the passages and find that it is blocked. At that moment they notice the eyes of some terrible creature behind them. Frodo approaches it with the Phial of Galadriel in one hand and Sting in the other, and the eyes retreat from the light. The hobbits continue quickly up the tunnel, but find the exit blocked by a barrier which turns out to be a giant spider's web. Frodo cuts the threads with his sword, and starts running towards the pass which is only a few steps away. Sam comes after him, yet so does the creature they've seen in the tunnel: Shelob, a huge spider. Shelob appears out of a side entrance into the tunnel and starts running towards Frodo. Before Sam can help him he is himself attacked by Gollum; after a desperate fight Gollum runs away.
Sam runs back to the path and finds Shelob bending over Frodo's body. This drives Sam mad with rage, and he attacks the giant spider; he could hardly have harmed her, but just when he is standing below her the monster throws herself to the ground so as to crush him. Sam holds his sword up, and it gives Shelob a deep wound; she retreats into a hole, defeated. Sam turns back to Frodo, who shows no signs of life. Sam despairs and can't decide what to do; at last, knowing that everything will perish otherwise, he decides to continue the Quest, and takes Frodo's sword, the Phial of Galadriel, and the Ring. After making the first few steps, however, he hears voices of Orcs coming near, and puts on the Ring. He finds that he can understand Orcs when he is wearing the Ring: it seems that there are two companies, one from the watch-tower on the pass and one from Minas Morgul. They take Frodo's body and carry it into a tunnel; Sam follows them, and listening to the Orc-captains he finds that Frodo is probably still alive, and will be imprisoned, not slain. The company of Orcs then passes through large double doors, which close before Sam could go through as well.