The Shire is a pleasant, peaceful land about 120 miles long (west to east) and 150 miles wide (north to south). Divided into four quarters or farthings, Northfarthing, Eastfarthing, Southfarthing and Westfarthing - it is a densely settled land of fields, farmlands, woods, streams, and villages. For the last 1500 years, it has been the homeland of most of the Hobbits. The original settlement was a land-grant from one of the last kings of Arthedain to refugees entering Eriador from Wilderland. It was later expanded through the addion of Buckland to the east, a narrow strip along the far shore of the Brandywine some 20 miles long but only about seven miles wide.
While well populated, the Shire has no true cities, the folk being dispersed across the whole country. The largest settlement, Michel Delving ('Great Burrows') in the chalky White Downs of Westfarthing, serves the seat of what government the Hobbits have. It houses the home of the Mayor as well as the headquarters of the Shirriffs, the Bounders, and the Post. Michel Delving also includes the Mathom House (the Shire museum) and is the site of the Free Fair (a septenial event).
A town of some size, it is unusual for the Shire in that, extensive as the namesake delvings are, a large portion of the town is aboveground.
Most of the other large population centres owe their numbers to being the home of a large and prosperous extended family, such as the Great Smials at Tuckborough. The Tooks live in Great Smials, while Tuckborough itself is largely populated by servants and workmen employed by or dependent in some way upon them. Similarly Brandy Hall in Buckland is the home of the Brandybuck clan, with the rest of Buckland serving as home to their friends, followers, retainers, and more distant relations. Most of the villages that dot the landscape are home to only one or two hundred Hobbits. Bilbo's grand birthday party, with its 144 invited guests, included virtually everybody in the nearby village of Hobbiton and the neighbourhood once the cooks, servers and other party staff were added in.
For such a small country, the Shire has a great variety of terrains: hills, river valleys, bogs, woodlands (thickening to forest toward the northen border), marshes, moors, and open downs. Aside from its unique native architecture, few other points of interest to a stranger passing though, except perhaps the Three-Farthing Stone, near the centre of the Shire just southeast of Bywater.
Early in the Fourth Age, King Elessar declares the Shire off-limits to Men. A second expansion, Westmarch, is added a generation after the War of the Ring (one of the original pioneers being Sam Gamgee's oldest daughter), extending the western border of the Hobbits' land from the Far Downs to the Tower Hills. The Shire prospered greatly during the Fourth Age, not just sharing in the general improvement of conditions the rest of Eriador experienced with the renewal of the North-kingdom, but also establishing new ties with other realms as the result of friendships that grew during the Quest of Erebor and the War of the Ring.
Woody End was a forest in the Eastfarthing of the Shire. It was located in the farthest southeastern tip of Green-hill country. It is about eight miles in diameter. Learn how to make the hollow in the tree where the Hobbits hide from a Black Rider.
Farmer Maggot was a Hobbit who at the time of the War of the Ring owned a farm called Bamfurlong in the Marish in the Eastfarthing of the Shire. This article not only shows how to make the farm house but various outbuildings such as dog kennels and stables as well as various fields.
Bucklebury Ferry was a raft-ferry used as the second main crossing point of the Brandywine River from the Shire to Buckland, after the Brandywine Bridge (which is ten miles further north). This article shows you how to make the jetty, ferry and the house as seen in the Fellowship of the Ring movie.
Crickhollow is a small settlement in Buckland, located a short way to the northeast of Brandy Hall. Its most notable spot is an isolated house standing back from the lane in the middle of a wide lawn. It is surrounded by low trees inside an outer hedge, and there are no other dwellings nearby. This house is occasionally occupied with Brandybuck Hobbits who grew tired of the often crowded Brandy Hall.
Old Man Willow was a great willow tree of the Old Forest; he was the root cause of much of the Forest's anger and hatred toward the trespassing of the walking things that pass through there. Learn how to make Old Man Willow in this article. The technique discussed within could also be applied to make generic trees.