The history of the event is perfectly explained in the following article by local historian Katherine Barker;

“Pack Monday is Sherborne’s only surviving medieval street fair.  Our earliest eye-witness account dates to the 1790s, a colourful description of the wide range of itinerant (and local) traders and entertainers ‘the ginger-bread men and the bustle, the horses and carriages and mules, the fiddle playing and the frolicking’ - and the drinking.  ‘Then the town comes alive’ - and it still does.  The writer remembers the cattle and sheep market in what is now the Hound Street car park and in 2012 met a lady in her 90s who remembered the gypsies and the horse fair on The Green.  Pack Monday changes with the times.  We also find an early description of Teddy Roe’s Band which ‘ushered in the Fair parading the town with noisy shout.’  ‘Whilst some of the sleeping inhabitants deplored this, others respected old customs ‘delighting in the deafening mirth.’  Things are much the same today! 

On Pack Monday the town is crowded with people, some travelling from a considerable distance.  But the Fair is little advertised – so how do they know which Monday?  The ‘deciding date’ of Pack Monday has clearly been handed on down the generations by word-of-mouth.  That is, the first Monday after the 10th October.  This places the Fair during Michaelmas-tide when the harvest was in, contracts completed and workers ‘signed off.’  It is suggested it was thus once known as ‘Pact Fair.’  Fair rights are still held by the Lord of the Manor (managed by today’s Sherborne Castle Estates) which is an indication of its considerable age.  It was the writer of this handout who recently noted that 10th October is the Eve of the Feast Day of St Probus whose name is presented by the pre-Saxon name of Sherborne.  Before the time of St Aldhelm, Sherborne was known as ‘Lanprobus’ a Welsh-style name meaning the ‘Christian settlement of [Saint] Probus.’  His church will have been located on The Green.  Teddy Roe’s Band may find its origins in an early bound-beating; ‘Teddy Roe’ from the processional hymn Te Deum laudamus; ‘Thee, O God we praise,’ known as the Te Deo.  Medieval fairs often took place on Saint’s Days.  We will never know whether the Fair goes back to the days before St Aldhelm and the Abbey Church, but the coincidence of the 10th October with St Probus is a remarkable one and hard to ignore.

There can be little doubt that Pack Monday is a unique survival.  Not Sherborne’s ‘dead’ history conserved in the stonework of our buildings but our ‘living’ history for us all to enjoy, to cherish and to enhance as to ensure its ‘protection’ on into the 21st century and beyond.”