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|Location||Northern Mirkwood, west of the Esgaroth|
The Woodland Realm was established by Oropher, a Sindarin lord of Doriath, after the War of Wrath. Unlike most Sindar Oropher and his household declined the Valar's offer to depart Middle-earth for Valinor. Instead he migrated eastward and became the King of the Nandor of Greenwood the Great. Oropher and his household quickly adopted the language and customs of the Wood-elves, wishing to return to a simple existence natural to the Elves before they had been disturbed by the Valar.
For the duration of the Second Age the Woodland Realm encompassed the entirety of Greenwood, with its capital at Amon Lanc. It maintained closed contact with the neighbouring Silvan realm of Lórinand and its king Amdír, who was also a Sindar refugee.
In S.A. 3430, Oropher and Amdír led their combined forces against Sauron as part of the Last Alliance of Elves and Men. During the Battle of Dagorlad the Silvan contingent refused to obey the orders of the Noldorin king Gil-galad, instead charging the enemy alone. They fought valiantly, but being ill-equipped and outnumbered most were slain, among them Oropher.
Oropher's son, Thranduil, succeeded him as king of the Woodland Realm and ruled for the duration of the Third Age. At some point during the first millennium, perhaps due to depopulation following the Battle of Dagorlad, the capital at Amon Lanc and most of the forest south of the old Dwarf road was abandoned. From this time the Silvan elves dwelt mainly in the Emyn Duir, or Dark Mountains.
Around T.A. 1050 an evil entity known as the Necromancer (later identified as Sauron) inhabited the abandoned halls of Amon Lanc, and Greenwood grew infested with Orcs and giant Spiders. The Wood-elves were pushed yet further north by this darkening, and many landmarks were renamed: Greenwood became Mirkwood, the Emyn Duir the Mountains of Mirkwood or Emyn-nu-Fuin, and Amon Lanc was known as Dol Guldur, the Hill of Sorcery.
By the middle of the Third Age the Silvan Elves of Mirkwood were much reduced in number and confined to the lands north of the Forest River, living mainly in Thranduil's halls. They also become increasingly withdrawn and wary of strangers, though they did trade with the neighbouring realms of Erebor and Dale, and imported wine from Dorwinion via the River Running. The former traffic came to an end upon with the destruction of Erebor by the dragon Smaug in T.A. 2770, who also attacked the Woodland Realm itself, putting further pressure on the beleaguered elves.
Quest for Erebor
In T.A. 2941 Thranduil's people came across a band of Dwarves while feasting in the forest. Perhaps still resentful over the Dwarves' role in attracting Smaug to their borders, or simply cautious, they imprisoned them for trespassing onto their lands. The Dwarves' leader, Thorin Oakenshield, however, would not reveal the purpose of their journey from their halls far to the west in Eriador. And after a few days imprisonment the dwarves escaped with the help of their companion, the hobbit Bilbo Baggins who had avoided capture using a magic ring.
Some time later the elves heard that Smaug, provoked by the escaped Dwarves, had left Erebor to attack Lake-town where he was slain by Bard the Bowman. Thranduil immediately assembled an army to claim part of the dragon's hoard in compensation for the destruction it had caused to the Woodland Realm. On the way they met messengers from Bard seeking aid for the people of destroyed Lake-town. Thranduil accepted, bring food and helping the people erect shelters for the winter. He and Bard then joined forces and marched north to claim the dragon's hoard and divide it between Bard, the people of Lake-town, and the Wood-elves.
On arriving however they found Thorin and his company alive, and he refused to relinquish his claim on any of the treasure and had secured Erebor against an assault. Thranduil and Bard then lay siege to the Dwarves, who awaited aid from their relatives in the Iron Hills to the east. Hoping to avert battle, the hobbit Bilbo Baggins earned the respect of Thranduil and was named 'Elf-friend' by delivering the Arkenstone to the Wood-elves and Men so they could use it to bargain with Thorin. Negotiations were cut short however by the arrival of a host of Orcs and Wargs from the Misty Mountains. In the ensuing Battle of Five Armies many Wood-elves were slain, as was Thorin Oakenshield, but afterwards an agreement was reached as to the division of the dragon hoard.
In the same year the White Council led by Gandalf drove the Necromancer from Dol Guldur. The lifting of this shadow and the death of Smaug gave the Wood-elves the first period of peace they had experienced in two millennia. Though some animosity between them and the Dwarves of Erebor lingered.
War of the Ring
This peace was broken by the outbreak of the War of the Ring in T.A. 3018. Sauron, now revealed as the evil presence which had abandoned (not, as it had been thought at the time, driven out of) Dol Guldur in 2941, from his rebuilt stronghold in Mordor sent a Nazgûl to reoccupy Dol Guldur. On 20 June a force of orcs attacked the Woodland Realm from this base, the purpose of this raid being to provide a distraction and facilitate the escape of Gollum who had been entrusted to Thranduil's care by the Ranger Aragorn.
In the wake of this Thranduil sent his son, Legolas Greenleaf, to deliver news of Gollum's escape to Aragorn and Elrond in Rivendell. Upon arriving Legolas participated in the Council of Elrond where the full details of Sauron's resurgence were revealed. Legolas was chosen to represent the Elves in the Fellowship of the Ring, and journeyed with the Ringbearer Frodo Baggins towards Mordor. After the Breaking of the Fellowship Legolas continued to accompany Aragorn, fighting in the Battle of the Hornburg, the Battle of the Pelennor Fields and the Battle of the Morannon. Legolas also developed a close friendship with the dwarf Gimli, son of one of Thorin's companions: Gloin. This friendship did much to improve relations between the two peoples.
Meanwhile, Sauron attacked the Woodland Realm in force, resulting in the bloody Battle Under Trees. Thranduil led his forces to victory, however, and then set about a campaign to clear Mirkwood of orcs and other evil beings. On Elven New Year he met Celeborn, the king of Lothlórien, and the two agreed to rename the forest Eryn Lasgalen. It was the divided: Thranduil was to rule north of the mountains, the forest south of the Narrows become East Lórien and the rest was given to the Beornings.
The eventual fate of the Woodland Realm is unknown. Legolas, having seen the sea during the War of the Ring, eventually sailed west to Valinor, reputedly with Gimli at his side. Like all Elves the people of the Woodland Realm were destined to either leave Middle-earth for Valinor or to 'fade' and become rustic woodland spirits. Given Oropher and Thranduil's refusal to leave Middle-earth at the end of the First Age was rooted in a desire to 'live naturally' as Elves had before being contacted by the Valar it seems likely that the latter was the fate of Thranduil and most of his people.