The origins of the fair are unknown, though it must be of some antiquity as John Hutchins in the second edition of his History and Antiquities of the County of Dorset (1815) states that it has been an 'immemorial custom', for boys and young men to blow horns in the evenings in the streets for some weeks before the fair "to the no small annoyance of their less wakeful neighbours". The fair was ushered in by cows' horns and by the ringing of the great bell at a very early hour of the morning.
Many such fairs were held around this time of year (see Nottingham Goose fair here and Horning the Colts here). The harvest was in, livestock and produce needed to be sold on, and contracts were completed and workers ‘signed off’. This may be the origin of the name - the word 'pack' may be derived from 'Pact Fair’, although folklorist Steve Roud suggests in his excellent 2006 book The English Year that it more likely refers to the day on which workers packed up their belongings at the end of the annual term of employment. A third theory has it that it references the many itinerant sellers and their wares (as in ‘pack-man’ or ‘packhorse’) who would descend upon the town for the fair.
Mention of blowing horns brings us to one of the fair's more interesting - or annoying to some residents, presumably - customs: Teddy Roe's Band.
In William Hone’s Every Day Book of 1826 he states that the fair and its noisy announcement originated at the completion of the building of Sherborne Abbey in 1490 when the workmen packed away their tools and 'held a fair or wake, in the churchyard, blowing cows' horns in their rejoicing'. According to tradition, the instigator of this behaviour was the masons' foreman Teddy Roe (or Rowe). It was he who decided that the best way to celebrate a job well done was to form an impromptu cow's-horn band and to embark on an epic, noisy, tuneless, all-night bender.
And so it has continued for over 500 years with Teddy Roe's Band going about the town at Midnight on the eve of the fair following the Abbey bell striking 13, for some long-forgotten eccentric reason.
The band then goes around blowing bugles, bashing dustbin lids together and beating on pots and pans with kitchen utensils until 4am when a 15-minute peal of bells brings things to a rousing climax. And, if that were not enough, the 'band' often holds 'rehearsals' in the month leading up to the fair. There was an attempt to ban the practice in 1963 but that was never going to work, was it?
Incidentally, an alternative origin for the band lies with the ancient practice of Beating the Bounds - it could be that ‘Teddy Roe’ is a mispronunciation of the processional hymn known as the Te Deo (Te Deum laudamus or ‘Thee, O God we praise.’)
Photos of the band are rare and poor of quality as their performance takes place at night. But there are plenty of the fair itself. 
Returning to Hone's Every Day Book of 1826. he provides us with a picturesque description of the event: 'There is a mart for the sale of horses, cows, fat and lean oxen, sheep, lambs, and pigs; cloth, earthenware, onions, wall and hazle nuts, apples, fruit trees, and the usual nick nacks for children, toys, gingerbread, sweetmeats, plums, &c. &c. with drapery, hats, bonnets, caps, ribbands, &c. for the country belles, of whom, when the weather is favourable, a great number is drawn together from the neighbouring villages
He also includes a list of some interesting exhibits, including: 'the learned pig, the giantess and dwarf, the menagerie of wild beasts - Mr Merry Andrew cracking his jokes. Rebecca Swain with her black and red cock. pricking in the garter, raffling for gingerbread, the Sheffield hardwareman, sporting a worn-out wig and large pair of spectacles.'
You'll have to use your imagination to visualise that.
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