|Location||Northern Mirkwood, west of the Esgaroth|
|Language||Sindarin, Silvan Elvish, Westron|
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 from 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.
Originally Oropher's realm encompassed the entirety of Greenwood, with its capital at Amon Lanc. However, during the Second Age he and his people migrated north three times. According to one tradition, the first movement was northward beyond the Gladden Fields, due to Oropher's desire to distance himself from the increasing encroachments of the Dwarves of Moria and his resentment of the intrusions of Celeborn and Galadriel in Lórien. However his people did maintain constant intercourse with their kin west of the Anduin. Oropher was also disturbed by the reports of Sauron's rising power and by the end of the Second Age he dwelt in the western glens of the Emyn Duir or Dark Mountains and his people lived north of the Men-i-Naugrim or Dwarf-road.
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.
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 retreated yet further north 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 They also become increasingly withdrawn and wary of strangers, though they did trade with the neighbouring realms of Erebor and Dale, and imported wine from Dorwinion via the River Running.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 were disturbed by 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, refused to reveal the purpose of their journey from their halls far to the west in Eriador. After many days of imprisonment the dwarves escaped with the help of their companion, the hobbit Bilbo Baggins who had avoided capture using a magic ring.
Sometime 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.
War of the Ring
Sauron, now revealed as the evil presence which had abandoned (not, as it had been thought at the time, driven out of) Dol Guldur, from his rebuilt stronghold in Mordor sent three Nazgûl to reoccupy Dol Guldur in 2951. On 20 June 3018 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, on 15 March 3019 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.<name="Great"/>
The eventual fate of the Woodland Realm is unknown. In Fo.A. 120 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.
- ↑ 1.0 1.1 1.2 1.3 1.4 J.R.R. Tolkien, Christopher Tolkien (ed.), Unfinished Tales, "The History of Galadriel and Celeborn", "Appendix B: The Sindarin Princes of the Silvan Elves"
- ↑ 2.0 2.1 J.R.R. Tolkien, Christopher Tolkien (ed.), Unfinished Tales, "The Disaster of the Gladden Fields", note 14
- ↑ J.R.R. Tolkien, The Lord of the Rings, Appendix B, "The Second Age"
- ↑ 4.0 4.1 4.2 4.3 J.R.R. Tolkien, The Lord of the Rings, Appendix B, "The Third Age"
- ↑ J.R.R. Tolkien, The Hobbit, "Flies and Spiders"
- ↑ J.R.R. Tolkien, The Hobbit, "Barrels Out of Bond"
- ↑ J.R.R. Tolkien, The Hobbit, "Fire and Water"
- ↑ J.R.R. Tolkien, The Hobbit, "The Gathering of the Clouds"
- ↑ J.R.R. Tolkien, The Hobbit, "A Thief in the Night"
- ↑ J.R.R. Tolkien, The Hobbit, "The Clouds Burst"
- ↑ J.R.R. Tolkien, The Hobbit, "The Return Journey"
- ↑ J.R.R. Tolkien, The Hobbit, "The Last Stage"
- ↑ J.R.R. Tolkien, The Lord of the Rings, Appendix B, "The Great Years"
- ↑ J.R.R. Tolkien, The Lord of the Rings, The Fellowship of the Ring, "The Council of Elrond"
- ↑ J.R.R. Tolkien, The Lord of the Rings, Appendix B, "Later Events Concerning the Members of the Fellowship of the Ring"