Stow-on-the-Wold, originally called Stow St. Edward or Edwardstow after the town's patron saint Edward, probably Edward the Martyr, is said to have originated as an Iron Age fort on this defensive position 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. It is likely that Maugersbury was the primary settlement of the parish before Stow was built as a marketplace on the hilltop nearer to the crossroads, to take advantage of passing trade. 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 Evesham Abbey.
On 21 March 1646 the last battle of the first phase of the English Civil War took place one mile north of Stow on the Wold. After initial royalist success, the superiority of the parliamentary forces overwhelmed and routed the royalist forces. Fleeing the field, the royalists fought a running fight back into the streets of Stow where the final action took place, culminating in surrender in the market square.
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The town is part of the Stow electoral ward. The ward includes the parishes of Stow, Maugersbury and Swell. In 2010 the total population of these parishes was 2,594.
Stow-on-the-Wold has an active Parish Council with 10 members. The current Mayor is Michael Curtis.
Stow is represented on Cotswold District Council by Liberal Democrat Councillor Dilys Neill who was elected in a by-election in September 2016. The village is also represented on Gloucestershire County Council by Conservative Councillor Nigel Moore who represents the Stow Division.
In 1330, Edward III set up an annual 7-day market to be held in August. In 1476, Edward IV replaced that 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 charter 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. 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 known as "tures" 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.
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 moved 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.
There has been controversy surrounding Stow Fair. The large number of visitors and traders has attracted more vendors not dealing in horses. In the past local businesses used to profit from the increased custom but in recent years most pubs and shops close for 2 or 3 miles around due to the threat of theft or vandalism.
Stow played a 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 the Battle of Stow-on-the-Wold, with hundreds of prisoners being confined for some time in St. Edwards.
Given its exposed spot on the top of Stow Hill, the town is often referred to with the couplet "Stow on the Wold, where the winds blow cold"."Stowe-on-the-Wold, Where the wind blows cold. Where horses young and old are sold, Where farmers come to spend their gold. Where men are fools and women are bold and many a wicked tale is told. High on the freezing Cotswold." etc.
The funeral of John Entwistle, the famous bass guitarist of the Who, was held at St Edward's Church Stow-on-the-Wold on 10 July 2002.
Stow-on-the-Wold was prominently featured in the eleventh episode of series 6 of Top Gear, when Jeremy Clarkson reviewed the Ford F-Series there. He chose to film it there because it's a typical village in the English countryside, as Jeremy compares it to the American countryside in the episode.
Several roads link Stow to the surrounding villages. The Fosse Way (A429), which runs from Exeter to Lincoln; the A424, which runs from Burford, into the A44 and into Evesham; and the A436, which connects Cheltenham and Gloucester with Stow.
From 1881 until 1962, Stow was served by Stow-on-the-Wold railway station which was on the Great Western Railway's Banbury and Cheltenham Direct Railway. The nearest railway station is now Moreton-in-Marsh (approximately 4 miles from Stow). This station is on the Cotswold Line from Hereford to London Paddington. An alternative is Kingham railway station (approximately 5 miles from Stow) on the same line.