Excerpts from:

A Treatise on the Situation, Manners, and Inhabitants of Bree-land

As writ by Oddvar of the Blue Mountains and Dalton Willow of Bree, T.A. 3015

Bree-land

Bree is the chief village of Bree-land, atop the Bree-hill at the crossroads of the Great East Road and the Greenway. Staddle is a settlement opposite Bree on the Bree-hill, primarily populated by Halflings. Combe is ten or so miles from Bree eastward, and Archet near it borders the Chetwood. All of these are self-governed, independently ruled with no Lord around. Surrounding these were tamed woodlands and plains, with a few lakes, and old ruins of Men. 

Stone houses of Men line the road in Bree numbering at a few hundred, with the holes of Hobbits on the slopes above them. There are many though without homes, in Beggar's Alley. For travelers. a tavern older than Bree-lander memory marks a meeting-place for many, called the Prancing Pony.

Staddle claims to be the oldest settlement of Halflings in Middle-earth. It is close to Bree and there is good friendship between the two. It is known for the pipe-weed grown there, comparable to that of the Shire. 

Combe is situated in a small valley a few hills from the Bree-Hill, home to more rustic farmers, caring little for those of the city, and rarely receives travelers, them preferring to venture instead to Bree.  Predominantly inhabited by Big Folk. Represented in their flags by three trees.

Archet is a successful village nestled in the Archet-dale, a valley bordering Combe, thriving and busy, with people much like that of Combe, few Hobbits. Its success is undermined however, by robbers waiting in the woods, who recently have taken to raids upon the common folk. 

Bree-landers

The Men of Bree are short and broad, with dark hair, and take surnames like the merchants of Gondor instead of their fathers' names. These surnames are typically taken from local plants, Rushlight for instance. They are jovial and pride themselves upon independence. They are more friendly with outsiders than other Men, but are still wary of the swarthy Southrons who come up the Greenway, and though eager to listen to strange tales of wanderers, made no friends with them. Many Hobbits live in Staddle, but a few live in Bree, and in character they are mirthful and carefree, like the Hobbits of the Shire, but there is some rivalry between them. The most common families of Hobbits in Bree-land were the Bankses, Brockhouses, Longholeses, Mugworts, Sandheavers, Tunnellys, and Underhills. Bree-landers do not travel, except perhaps for the Hobbits of Bree who venture westward into the Shire, but even then only go so far as the edge.

The educated merchants of Bree read Westron in Cirth; however, this is a small minority, the majority of Hobbits and Men unable to read. Lutenists are popular, as well are singers, and actors perform plays, most commonly in Bree. Throughout the villages, swimming and dancing are common amongst all peoples.

Bree-land dress is simple and practical, and mostly rough spun, however successful merchants have been able to trade for finer materials. The mensfolk wear jerkins and cloaks, with jackets in the winter, and cloaks in the rain, over long shirts. The womensfolk take to dresses or skirts, and shawls and cloaks. Clothes are commonly undyed amongst the most poor, but with Hobbits and most other Men, take on color, and in Hobbits, much of it. In Bree-land, clasps are for the most part simply made and unadorned, though Men of the Watch will carry clasps bearing the symbols of their service. 

The Bree-folk typically carry but simple knives, and hunters keeping bows, but Watchers can be seen bearing sword, shield, and spear. They wear mail and leather, and with these simple tools keep the four villages safe. These Watchers however only will defend; they are no army. 

Marriage and Families in Bree-land

The bond of matrimony in Bree-land is a ring worn upon the fourth finger of the left hand, of varying quality depending on the means of the couple. In marriage the groom and bride will wear their best clothes they own, and on the day a dowry is given to the groom from the bride's father. The most common time for weddings is the later part of Chithing (Known in the Shire as Astron), when flowers begin to bloom.

The Hobbits of the Four Villages are very much like those of the Shire in most every manner. The Men of Bree however, require mentioning. They raise their children to take manner after their parents, and inherit occupations in the same fashion, teaching them from boyhood. However, the Men of Bree value mirth; dancing and practical jokes abound amongst children.

Leadership of Bree-land

There is not any office passed by birthright or that has absolute power; the Men and Hobbits of Bree elect leaders for themselves whom they call Mayors, chosen from the populace every Mid-year's Day. There is a deputy who governs in the Mayor's absence, chosen by the Mayor himself. Men on his council, called Aldormen, guide the Mayor and typically includes the Captain of the Bree-town Watchers by precedent and necessity. The other three of the Four Villages do not have mayors. The folk of the Four Villages will each assemble upon the full moon.

The Watchers of Bree-land

There is no army in Bree, only the Watchers whose primarily role is one of internal policing, and who do not venture far out of town. In Combe and Archet the Watchers will search for brigands, and Bree, with more Watchers, will take to the Bree-fields in search of outlaws. There is rumor of Orcs to the North, in Trestlebridge, but it has held steady at time of writing, and the Four Villages are safe. 

Food in Bree-land

Bree is famed for its cider, made from the apple trees around the Bree-hill. Bree-landers are fond of stew, cakes, and pies, the Little Folk perhaps overfond. Hunters of the Chetwood will bring in conies, deer, and birds, and fish are often catch in Bree-land's lakes. Chickens, eggs, and pork are often consumed, alongside local vegetables common to the region. Aurochs however are rarely consumed; they are beasts of burden and very valuable to any farmer.

Death in Bree-land

Bree-landers bury their dead in the ground, in graveyards with stone walls, and mark headstones and footstones for deceased. Many old graveyards exist, from before memory and days known only in fleeting legend, Of note are the Barrow-downs on southward low-lying hills, where many men of old are said to have ventured. However, none have been there in recent memory, for fear of fell beings that there slumber.