Tookbank, and the Tookland generally, must have been settled after the Shire was founded in III 1601. Given that the region was more than fifty miles westward of the Brandywine Bridge, it probably took some time before the village was settled. We do know that the Tooks were a well established family by III 2340, when Isumbras I became the first Took Thain, so it seems fair to assume that Tookbank would have existed by that date (and probably for some time beforehand).

To call the detour 'significant' is perhaps an understatement. For example, Hobbiton was less than twenty miles from Tuckborough as the crow flies, but to travel between the two towns by road would have involved a trip of some forty miles east to the Brandywine Bridge, about ten miles south to Stock, and then another fifty or so miles back westward to the final destination of Tuckborough.

This is all based on the detailed map of the Shire included with The Lord of the Rings, which shows no road between the two towns. Of course, an obvious third possibility is that a road or track did exist, but was simply omitted from the map.