Stow on the Wold is said to have originated as an Iron Age fort on this defensive postion on a hill. Indeed, there are many sites of similar forts in the area, and Stone Age and Bronze Age burial mounds are common throughout the area. The town began to grow as a result of trade along the Fosse Way (a Roman Road). Originally the small settlement was controlled by Abbots from the local Abbey, and when the first weekly market was set up in 1107 by Henry I, he decreed that the proceeds go to the Evesham Abbey. In 1330, Edward III set up an annual 7-day market to be held in August. This was replaced by Edward IV in 1476 with two 5-day fairs, two days before and two days after the feast of St Philip and St James in May, and similarly in October on the feast of St Edward the Confessor (the saint associated with the town). The aim of these annual fairs was to establish Stow as a place to trade, and to remedy the unpredictable passing trade. These fairs were located in the Square, which is still the town centre.
As the fairs grew in fame and importance, the town grew more prosperous, and the fairs became bigger. Traders who once only dealt in livestock, now dealt in many handmade goods, and the wool trade always stayed a large part of the trade. Reportedly, 20,000 sheep changed hands at one 19th century fair. Many alleyways run between the buildings of Stow into the market Square; these once were used in the herding of sheep into the Square to be sold.
Nowadays, however, the Fair has changed considerably. As the wool trade declined, people began to trade in horses, and these would be sold at every Fair. This practice still continues today, although the Fair has been relocated from the Square, and is currently held in the large field towards the village of Maugersbury every May and October. It is still a very popular Fair, with the roads around Stow being blocked for many hours on the day as people visit for the day. Even in the rain, the Fair continues to draw visitors, and the field is frequently filled with traders and customers.
More recently, there has been controversy surrounding Stow Fair. The large number of visitors and traders has attracted more vendors not dealing in horses, and often they bring with them an increase in vandalism, and sometimes in the crime rate. In the past, local businesses used to profit from the increased custom. Nowadays, most pubs and shops close for 2 or 3 miles around. In the run-up to the most recent Fair, there was an enormous amount of public attention, and a debate and vote were held to decide what should be done. There are people in Stow who would like it abolished; others want it to stay unchanged; the majority, it seemed, said they would like more policing and more street cleaners, and the last Fair passed fairly well. However, the future of the Fair still remains uncertain.
Stow's chief claim to history is its role in the English Civil War. A number of fights took place around the area, the local church of St. Edward being damaged in one such skirmish. On 21 March 1646, the Royalists, commanded by Sir Jacob Astley, were defeated at Stow, with hundreds of prisoners being confined for some time in St. Edwards.
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