Tookland was a wide region of the Shire's Westfarthing that was the historical province of the Took clan, and so of the hereditary Thains of the Shire. The Tookland lay to the south of the East Road, with its chief and central township at Tuckborough in the Green Hills. There, burrowed into the hillsides, was the famous and historic home of the Tooks, Great Smials. Somewhat to the west of Tuckborough lay the smaller of the Tookland's main settlements, Tookbank.
During Sharkey's occupation, the Tooks were fortified in their smials and didn't allow any ruffians to enter, having shot three for prowling and robbing. They became nastier and kept a close watch. Around the time of the Battle of Bywater, Thain Paladin Took II raised all the country and commanded some troops to drive them away to the south, and sent a messenger to Bywater.