How this story came to be...

tl;dr (as they say): The setting and backdrop for the Tooks and Tookland in my stories are drawn from J.R.R. Tolkien's casually dropped hints and details. 

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Against the grand backdrop of the Quest, with its sweeping vision and lovingly crafted descriptions, Tolkien scattered hints about places and people groups that give a sense of depth and layers to the history of his creation. One such people group is the Tooks, a Hobbit clan descended from the early (pre-Shire) Fallohide branch of Hobbitry. Tooks appear in three of the four Travellers' family trees. 

Tolkien's thoughtful world-building made it possible to gather up the threads of his hints and weave them into some sort of tapestry. He describes the Tooks as a clannish bunch who are seemingly suspicious of strangers as a whole, notwithstanding the Old Took's friendship with Gandalf and Pippin's quick connection with Beregond. They were the first to start shooting at Lotho's Men, as Farmer Cotton told the returning Travellers, and hunted any ruffians that came on their land. 

The Green Hill country gives the impression of being wilder and less-settled than the inhabited parts of the Shire Tolkien describes. It is easy to envision high, rolling hills, tumbling streams and waterfalls, isolated copses and stretches of woodland that, moving eastward from Tuckborough or southeastward from Bywater, become a solid blanket where the Woody End and the Green Hill Country intersect. One might imagine country suited to hunters and wanderers, along with shepherds watching over flocks of sheep or herds of goats and smallholders living in cosy smials tucked into hillsides, tilling crops on a small scale, and raising relatively small herds of shaggy hill cattle for their milk, cheese and meat. The wooded areas might feature foresters or woodcarvers or furniture-makers or even charcoal-burners, some living in small communities in the woods, like The Yale, and others scattered and solitary. The more solitary among them, whether wanderers or rooted in place, might well be seen as peculiar by the hobbits living in the more settled and populous areas. 

One striking feature of the Green Hill Country is the lack of roads. For example, Tolkien's maps feature no roads connecting Tuckborough with Tookbank or Waymeet or Bywater. And even though a road runs from Tuckborough to Stock which lies near the banks of the Brandywine River, the author's description of the Stock Road at the time the Travellers first set out on their journey includes "a narrow road, that went rolling up and down.... It climbed away from the main road in the Water-valley, and wound over the skirts of the Green Hills towards the Woody End, a wild corner of the Eastfarthing." Tolkien also mentions a "deeply cloven track between tall trees ... a dry fir-wood [just over the top of a hill].... [T]he road ran steeply down into a hollow and disappeared" as well as "a stream at the foot of the hill" featuring "a little fall where the [icy-cold] water fell a few feet over an outcrop of grey stone" and "dived under the road" at the bottom of the slope. After a bit more description, Tolkien adds that "[t]his way was not much used, being hardly fit for carts, and there was little traffic to the Woody End." 

Yet the Stock Road is the only road on the map ('A Part of the Shire') connecting Tuckborough and the Great Smials to other places, whether inside or outside the Tookland! 

In later stories, I came to explain the neglected condition of the Stock Road as stemming from a serious breach that occurred between the Great Smials and Brandy Hall during the time of Lalia the Fat, when her son Ferumbras was Thain. After Lalia's death, Ferumbras gave little attention to keeping the roads in the Shire for a king that felt unreal to him. In particular, since he never used the Stock Road himself, Ferumbras saw little to no reason to devote any resources to its upkeep and repair. 

Also, in my version of the Shire, sometime during his last few years as Thain, Ferumbras moved Tookland's treasury to a more secure location which he kept secret. But Ferumbras died suddenly, and Paladin became Thain. Since the treasury had "gone missing", Ferumbras's successor had no resources to pay for repair and upkeep of the roads, including the neglected Stock Road, much less anything else.

In my stories set in the Fourth Age, I have dotted a series of inns along this rather forlorn and deserted track ("forlorn and deserted" according to Frodo's description, anyhow). My imaginings include an explanation for this seeming contradiction as follows: 

After the ruffians were thrown out, Tolkien describes a time of prosperity in the Shire. One of the Travellers hailed from the wild Green Hill Country, while the others called more settled parts home. Thus, under the Travellers' influence, travel might have picked up between the rest of the Shire and Tuckborough in the heart of the Tookland. In particular, considering Pippin and Merry's close relationship, the Stock Road would have seen an increase in traffic between the Great Smials and Brandy Hall, especially after the two close cousins became Thain and Master. It seems reasonable that Pippin, on becoming Thain, would have underscored the Thain's duty to keep the roads for the King. In support of his efforts, the recovery of Tookland's treasury about a year after Pippin became Thain meant that road-building and repair could be fully funded. 

A woodcarver or woodcutter or hunter living near the Stock Road, even during the period when the road was allowed to fall into disrepair, would be in prime position to take in travellers, earning a bit of extra coin by providing meals and possibly beds for those on the way from one place to another. A honey-hunter who kept track of colonies of wild bees (the forest equivalent of a beekeeper) might become known for brewing mead, and might build a common room onto his forest dwelling for locals – and eventually, travellers – to gather, which is perhaps how the Crowing Cockerel got its start, though eventually that establishment expanded its beverage offerings and became the home of "the best beer on the Stock Road".

As travel grew between Stock and Tuckborough, so did a few of the more favourably-situated inns, so that travellers would no longer need to camp along the 50-mile stretch but could sleep in comfort. Most of the innkeepers likely did not quit their day jobs (woodcutting, hunting, etc.), but some might have eventually ended up with bustling establishments, helped along by the Thain and Master of Buckland's scheme, after Pippin became Thain, to set up a pony relay about every ten miles along the Stock Road, thus providing a steady income for stabling and boarding the mounts provided and funded by the Thain and Master. 

Backtracking slightly, it's relatively easy to spin a mental picture of a very old roadway that has been in use for a long time ("deeply cloven track") but has fallen out of use, perhaps as the Tookland became more isolated under Ferumbras. Isolation and a challenging landscape provide a logical explanation for the ruffians' inability to overrun that area, added to Farmer Cotton's recounting of the Tookish resistance (he tells the returning Travellers that the Tooks started the shooting, Pippin's father called Lotho 'an upstart', and Lotho's men 'got no change out of [the Thain]'. Not to mention, 'and they won't let the ruffians come onto their land. If they do, Tooks hunt 'em'.) The Thain is also described in military terms in 'About Hobbits' as the 'master of the Shire-moot, and captain of the Shire-muster and Hobbitry-in-arms'. 'The Scouring of the Shire' also reveals that Paladin sent a hundred Tooks to the Battle at Bywater, and he himself led another large body to scour ruffians out of the Shire in the other direction from Bywater. 

Tolkien's descriptions of this wild land and its proud, untamed inhabitants led to the idea of the Thain's escort, made up of hunters who know the land like the fur on their feet and can shoot a bow with skill and accuracy. A shepherd or herd-hobbit or farmer would have his dogs to protect him from dangers in the wild. Shirriffs patrolled the Four Farthings, and one of their specified responsibilities was to deal with stray animals, which would have included dogs. Though Bilbo wandered by himself, it's easy to imagine that he wore Sting on his wanderings and could handle himself in a pinch. In this light, it is conceivable that the Tooks would have a tradition of protecting their leader. That train of thought underlies how the hobbits of the Thain's escort came about in my stories. 

Furthermore, the escort are quite determined and dedicated, by tradition and the oath they have sworn to protect their Thain, which Pippin finds inconvenient at best and smothering at its worst. 

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In terms of background, very early on, one of my earliest-written Fourth-Age stories laid out a timeline where Pippin, not long after he came of age, tricked the hobbit who was supposed to accompany him on forays in the wild Green Hill Country, and rode off by himself – into an ice storm, where he nearly died. His father blamed the escort to begin with, but as the situation grew worse, so did the consequences for Pippin's escort. As the estrangement grew between the Thain and his son, Pippin decided not to return to his homeland, and the Brandybucks offered him a responsible position as assistant to their Steward. Later, he became the Steward of Buckland in his own right, and served as Merry's right-hand hobbit. Though he eventually came to an understanding of some kind with his father, Pippin stubbornly remained in Buckland until Paladin's death. As his dying request, Paladin named Pippin to be the next Thain; thus, honour compelled Pippin to return to Tookland at last. It must also be said that Paladin did not repent of his harsh judgement towards the erring hobbit of the Thain's escort until he was on his deathbed.

(Because this estrangement saddens me, I later constructed an alternate timeline, as reflected in The Farmer's Son. But that does not come into this story.) 

Upon his return to take up the office of Thain, Pippin finds that Tookland's Steward, Reginard, for reasons of his own, has elevated the formerly disgraced escort to the position of Head of the Thain's escort. Once Pippin grasps the ruin he has made of that cousin's life, he leaves things as Regi has established them, perhaps as the start of his own attempt to make amends and right old wrongs. 

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