A high, domed green hill, often simply called 'The Hill' that dominated the landscape around Hobbiton in the Shire, and gave its name to the settlements of Underhill and Overhill that stood on its slopes. It lay to the north of Hobbiton, from which a road ran past the Hill and on to Overhill on its far northern side, and a minor lane also ran westward from its base. The Hill was large enough, and its slopes shallow enough, for it to be divided by hedges into several separate fields. Trees grew sparsely on its slopes, including one that stood prominently on its crown.1
Though much of the Hill was covered by open land, it was not uninhabited. Along its southern base was a row of three Hobbit-holes originally known as Bagshot Row, but the Hill was more famous as the site of the large and luxurious smial known as Bag End. Bag End was created by Bungo Baggins, probably in the late thirteenth century of the Shire-reckoning (that is, the twenty-ninth of the Third Age). Its doors and windows opened out from much of the southern side of Hobbiton Hill, and the extensive rooms within must have filled much of the Hill's interior. After Bungo's time, Bag End was occupied by his heirs Bilbo and then Frodo, until it was sold to Lobelia Sackville-Baggins when Frodo departed from the Shire.
The Hill was reshaped during the closing years of the Third Age. When Lotho Sackville-Baggins set himself up as the 'Boss' in the Shire, he used Bag End as his base of operations, causing Bagshot Row to be dug out, and rows of huts to be built around Bag End. Saruman took Lotho's place when he came to the Shire in the guise of 'Sharkey', and it was his death at the hands of Gríma that was considered to have brought the War of the Ring to a final end. That event took place on the steps of Bag End, and Saruman's spirit rose as a huge misty figure above the Hill before being dissipated by the wind. So Hobbiton Hill was witness to the last dramatic moments of the Great War of the Ring.
After their victory, the Shire-hobbits set about repairing the damage caused during the War. One of these changes was made to Hobbiton Hill, where the destroyed Bagshot Row was replaced by a new set of Hobbit-holes that were named simply New Row (but also jokingly referred to as 'Sharkey's End'). The great smial of Bag End was briefly occupied by Frodo Baggins, but after his departure into the West it was taken over by Sam Gamgee and his family. It evidently remained in the family for at least several generations: the last apparent mention we have of Hobbiton Hill is in the name of Samwise's great-grandson, who was known as Harding of the Hill.
This description is based on images of Hobbiton Hill created by Tolkien, though these vary in certain specific details. In particular, the lone tree on the crest of the Hill appears only in later drawings and paintings. A progression of these images can be seen in J.R.R. Tolkien: Artist and Illustrator.
Baggins Family, Bagshot Row, Belladonna Took, Bilbo Baggins, Bungo Baggins, Bywater Road, Halfred of Overhill, Harding of the Hill, Hobbiton, New Row, Old Gamgee, The Hill, Underhill, Widow Rumble
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