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Guildford's Dicey Maids, Surrey

It is tempting to view some of the odder charitable bequests found throughout the country as a way of keeping the name of the donor alive, rather than having an appreciable impact on the lives of the recipients. But in the case of the Maids' Charity in Guildford both ends are met.
For once a British folk custom is easy to date: on January 27 1674 John How or Howe (spelling being rather more flexible in those days) left £400, a fortune in that time, to buy land which in turn would provide the income to continue his charity. This entailed his trustees seeking out two maids working in the town (but not heaven forefend in an inn or pub), ensuring they were of good character, and then arranging for the Mayday event to decide which of the two would get the payment.
Rather cruelly this was at first a winner-takes-all event, with a decent sum being paid to the winner - currently £60, in Victorian times £10 or so; though the loser was able to contest the event for a further three years. The winner is barred from competing again. The chosen method of competing was the throwing of dice, rather an ungodly activity for a charitable bequest, though Dicing for Bibles at St Ives in Cambridgeshire has a similar structure.
Perversely, because at a later date the benefits of another charitable bequest, that of John Parsons, were provided for the loser, it is now the loser who wins more money than the winner.
Guildford is keen on retaining the tradition, and the mayor is expected to oversee the event , hosted by Guildford Poyle Charities and held at the Guildhall on Mayday. Housemaids are few and far between now, so domestic helpers are chosen to vie for the money instead.

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