Seven hundred and forty years after the founding of the Shire, Gorhendad Oldbuck crossed the River Brandywine from the Eastfarthing and started the building of Brandy Hall in Buck Hill, in a land hitherto unpopulated by hobbits. As Gorhendad's family grew, the Hall also expanded, and soon there was a flourishing community in the land between the River and the Old Forest.
The village of Bucklebury, lying close by Buck Hill, was considered Buckland's chief village, but the expanding population meant that many other villages soon grew up in the region, the largest of which were Newbury, Crickhollow and Standelf. The growing power of the Master of Buckland gained respect from those close by in the Eastfarthing, too; the lands of the Marish between Stock and Rushey also acknowledged themselves under the sway of Buck Hall.
The Bucklanders soon found themselves threatened by the strange trees of the Forest, and so built a vast hedge, the High Hay, stretching twenty miles along the eastern border of their land. This was not the only danger to threaten Buckland - in 2911 (Third Age), the year of the Fell Winter, the Brandywine froze and Buckland was invaded by white wolves.
Buckland was also the childhood home of Frodo Baggins, who returned here on his journey to Rivendell in 3018 (Third Age). He bought a house in Crickhollow, and claimed that he would be living there, but instead entered the Old Forest through the old Hay Gate, and left the easternmost of the Hobbit-lands.
Although similar in many ways to other hobbits, the Bucklanders did have certain peculiarities. Due no doubt in part to the Fallohidish blood of the Brandybucks, the hobbits of Buckland were somewhat more adventurous than their cousins in the Shire (while still conservative by the measure of many other races in Middle-earth). They enjoyed boating, an activity frowned upon by Shire-hobbits, and some of them could even swim.
When the Bree-folk ventured to the Shire, Buckland was their usual destination (though some ventured as far as the Eastfarthing), and so was rather more cosmopolitan (in hobbit terms) than the rest of the land.
Living under constant danger from the Old Forest, the Bucklanders were hardier and more suspicious than the usual Shire-hobbit. They were organised to deal with danger (through the famous Horn-call of Buckland), and they kept their doors locked at night, which was unusual in the Shire.