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In the year S.R. 1418
Strider and the Hobbits travelling east come out of the Chetwood and enter the Midgewater marshes. While walking during the day they are tormented by flies and midges, and their sleep in camp is distrubed by the drone of loud insects.
Gandalf continues riding east from Bree in pursuit of the Black Riders.
Strider leads the Hobbits east through the Chetwood north of the Road.
Gandalf leaves Bree before dawn upon Shadowfax, riding east in pursuit of the five Riders who passed through during the night.
In the cold before dawn the Black Riders attack the two locations to which they have traced Frodo: the house at Crickhollow to which he has moved, and the Hobbit rooms at the back of the inn at Bree. Fredegar Bolger has been watching the house at Crickhollow and flees as three Riders attack; for the first time in more than a century the Horn of Buckland is blown, and the only casualties by morning are the Buckland gate wardens who are trampled while attempting to impede the Riders' escape. At the Prancing Pony in Bree the Hobbits' rooms are ransacked, but they are not harmed as they passed the night with Strider in the parlour. As their ponies are missing, they must purchase Bill Ferny's underfed and overpriced pony, and depart Bree around ten o'clock in the morning before a crowd of onlookers. And after following the Road's course south and east around the Bree-hill, Strider leads them off the road toward the north.
By morning Gandalf reaches Buckland and finds the Hobbits in arms and the house at Crickhollow ransacked; in his haste he fails to interview the eyewitness Fatty Bolger, who alone could have told him that Frodo entered the Old Forest days before. Discovering one of Frodo's cloaks on the doorstep, he assumes that the Hobbit and his Ring have been captured and immediately sets out in pursuit. The Riders have dispersed but Gandalf follows the trail leading to Bree, arriving in the evening and learning from the innkeeper Butterbur that Frodo departed that morning in the company of Strider. Gandalf expects his first night's rest in more than a week.
Frodo wakes inside of a barrow, one of the ancient hilltop crypts that line the downs east of the Old Forest; his companions Sam, Merry, and Pippin are unconscious beside him. He calls on Tom Bombadil and the four Hobbits are rescued from the Barrow-wight who ensnared them when darkness fell last night. As Tom empties the barrow of its treasure, and thus of its curse, he arms them each with a dagger from the hoard — and thus provides Merry with the blade with which he will strike the Witch-King at the Battle of the Pelennor Field in five and a half months, the same enemy whose servants killed the men buried in the barrow, and the enemy against whom the blade is imbued with spells.
The Hobbits ride north to the East-West Road and then east along it to Bree where they lodge at the Prancing Pony. They meet the Ranger called Strider, and Butterbur the proprietor of the inn finally delivers to Frodo the letter which Gandalf wrote to Frodo three months ago; and they become convinced that Strider is the “Aragorn”, son of Arathorn, whom Gandalf's letter tells them to trust. When they hear that Black Riders have been seen in Bree, Strider has them spend the night in a lighted parlor of the inn which they hope is less susceptible to attack than the first-floor Hobbit rooms in which they would otherwise have slept.
Reports that Gandalf gathers after entering the Shire indicate that only some of the Black Riders entered the district. Upon reaching the Hill, the wizard learns from Gaffer Gamgee that Frodo departed with the Gaffer's son Samwise six days ago, not two months earlier as urged in Gandalf's letter; and that a Rider arrived later the same evening, seeking the whereabouts of ``Baggins.'' The wizard fears the worst as he rides for the Eastfarthing.
Frodo, Sam, Merry, and Pippin wake, for a second morning, in the house of Tom Bombadil, and depart to continue their journey after breakfast. As his house lies on the eastern edge of the Old Forest, they by turning north hope to pass safely along the west edges of the Barrow-downs and so reach the East-West Road that will take them to Bree. Instead they stray too near a standing stone on a hilltop, and as night falls are ensnared by a barrow-wight and trapped in one of the ancient graves.
Gandalf reaches Sarn Ford one week behind the Black Riders and, crossing the Baranduin, enters the Shire from the south.
Frodo, Sam, Merry, and Pippin wake in the house of Tom Bombadil; deep rains pour upon the valley of the Withywindle as his wife Goldberry does her “autumn-cleaning.” They pass the day listening to his songs and tales, which draw them deep into the secrets and counsels of the Forest, and open out into remarkable vistas of the ancient lands lying to the east of the Shire. They spend a second and final night at his house.
Gandalf upon Shadowfax crosses the river Greyflood at the ford of Tharbad, passing from the Enedwaith into Hinhiriath. He will spend little more than two weeks west of the river before crossing back east across its tributary, the Mitheithel, at a point more than three hundred miles to the north.
At daybreak the journey of the Ring begins in earnest, as Frodo leaves his new house in Crickhollow and together with Sam, Merry, and Pippin passes under the Hedge that separates Buckland from the Old Forest. They hope by avoiding the roads to pass out of the Shire undetected by the cloaked Riders that have been pursuing them.
Through the day the trees of the forest force their path to bend southward toward the valley of the Withywindle where in the afternoon a great Willow traps the Hobbits. They are rescued by Tom Bombadil, who is passing up the river-valley on his way home from gathering some of the last of the season's water-lillies for his wife. The Hobbits follow him and are treated to dinner and warm beds at his house.
Gandalf for a second day rides upon Shadowfax across the Enedwaith.
Gandalf upon Shadowfax rides across the Enedwaith between the rivers Isen and Greyflood.
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In the year S.R. 1419
Bilbo Baggins turns one hundred and twenty-nine, and his birthday is celebrated by Frodo, Sam, Merry, and Pippin who have all returned just yesterday to Rivendell after leaving Rivendell with the Ring nine months ago.
The wizard Saruman reaches the Shire, having left his ruined fortress of Isengard more than a month ago. While for many years he deployed only spies into the Shire, he recently has been employing wealth and, finally, open violence in order to impose his own rule on the district. They have cut off access to the Tookland, since its Thain is opposing them and his Hobbits are shooting Men on sight; but the Tookland itself is alone in still remaining out of Saruman's power.
After eight final days of riding north, Gandalf and the Hobbits return to Rivendell accompanied by Elrond, his sons, and many Elves of his household. It has been more than four and a half months since Elrond and his advisors rode from Rivendell with Arwen, bringing her south to her wedding in Minas Tirith; at least seven months since the sons of Elrond departed Rivendell to ride south with the Dúnedain to fight alongside Aragorn; and only four days shy of nine months since the Hobbits and Gandalf left Rivendell on a cold night of late December bearing the Ring southward toward its destruction.
After a week of rest in Eregion among the ruins of the ancient Elven city, the time comes for the Elves to part. Celeborn and Galadriel head east with their companions over the Redhorn pass toward their forest of Lórien on the other side of the Misty Mountains, while Elrond, the Elves of his household, and Gandalf and the Hobbits continue north along the west side of the mountains toward Rivendell and the House of Elrond which lie slightly more than a week's ride to the north. It took the Hobbits a full two weeks to cross the same distance on foot when they marched south from Rivendell with the Company of the Ring, more than nine months ago.
The Hobbits and Elves riding north with Gandalf toward their homes reach Hollin and the trace ruins of the ancient Elven city of Eregion. They linger among the stones for a week, the Elves communing together one last time; for Celeborn will remain in Middle-earth, while his wife and Elrond and most of the other High-elves will soon take ship and pass into the West.
The Hobbits and Elves who ride north with Gandalf toward their homes come upon the wizard Saruman, who is also passing north. After a vicious exchange of words on the part of the ruined wizard, they continue north while he moves off to the northwest.
Aragorn and the Hobbits and Elves riding north come finally to Isengard. From Treebeard they learn that the wizard Saruman is no longer imprisoned in Orthanc. The Hobbits make their farewell to Treebeard, as do Celeborn and Galadriel whom he has not seen since more ancient times.
Legolas and Gimli bid the other riders farewell, and accept the invitation of Treebeard to ride north through Fangorn forest as they ride toward their homes in the northern Mirkwood (now named the Wood of Greenleaves following the victories of the Elves against Dol Guldur, as they will learn upon their return) — Legolas toward the city of the Wood-elves where the father reigns, and Gimli toward the great caves under the Lonely Mountain where he will find the old King Dáin Ironfoot has fallen in battle and his distant cousin Thorin III Stonehelm now reigning.
At sunset they approach the Gap of Rohan, the westernmost border of ancient Gondor, where Aragorn bids them farewell so that he may ride back to his Queen who waits in Edoras for both of them to return to Minas Tirith and being in earnest their reign. Aragorn and his knights do not turn immediately, but sit awhile upon their horses to watch the travellers disappear into the sunset, who in return see behind them the sunlight gleaming upon the harnesses and a final flash of green from the Elfstone.
Aragorn continues to ride north toward Isengard with the Hobbits and Elves who are now returning to the North following their involvement in the War of the Ring or, in the case of many of the Elves, their long ride to the south to see his wedding to Arwen. They come to Helm's Deep, where Gimli is finally able to show Legolas the beauties of the Glittering Caves that lie behind the Deeping Coomb, of which he became enamored when forced to flee there during the Battle of Helm's Deep more than five months ago.