Today Stow-on-the-Wold sits at the crossing of 3 major trunk roads, the A429 (Fosseway), A424 and A436 plus 2 secondary roads, the B4068 and the B4077, making it a very busy traffic hot-spot. This is no different from its history and explains how Stow-on-the-Wold has grown up where it is, being at the junction of The Jurassic Way, the Salt Way and the Roman Fosse Way. These original ancient tracks followed the high ground and enabled the carrying of goods for long distances so that eventually Stow became a convenient trading centre. 

Since Saxon times the area was under the control of the Abbott of Evesham who saw these crossing routes as an ideal meeting point and trading evolved. In 1107, Henry 1 granted the right to hold a weekly market. This was held on Thursdays in the area between the three main Ways, and this area now forms the Market Square, which remains an important meeting place and trading area to this day. A market is still held on two Thursdays each month. There are several tures or alleyways such as Fleece Alley leading towards the Market Square, which, it is believed, were used to control the passage of the sheep into the market-place from the pasture land behind the town. Contracts were agreed at the market cross in the Square, whose purpose was to remind merchants to trade honestly. The cross remains a key focus of the Square and its activities. 

During Plantagenet times, Stow thrived through the wool trade, with the addition of 2 annual five-day fairs granted in 1476 and together with the weekly market saw the sale of large numbers of sheep and fleeces together with foreign and British goods. Wealthy wool merchants would come to Stow-on-the Wold to purchase fleeces directly from source and as such spent a lot of time in the area setting up homesteads and putting a lot of money back into the community. Examples of this include the building of the School House in Church Street, the 6 Alms Houses in Church Walk and, it is believed, paying for the construction of the church tower.

Christian worship has taken place in Stow for over 1,000 years with the iconic St. Edward’s Church being built in 1107AD on the site of an earlier Saxon church. In the Doomsday Survey of 1086, part of the local manor owned by the Abbey of Evesham and close to St. Edwards Church was, at the time, called Edwardstow.

Royalist and parliamentarian armies passed through Stow-on-the-Wold several times during the first Civil War (1642-46) and a stand-off action was fought to the east of Stow in the summer of 1643 as the Earl of Essex's army marched to relieve Gloucester.  King Charles I also stayed in the King’s Arms in May 1645, but the town is perhaps best known as being the final location of the last battle of the first Civil War. Sir Jacob Astley, leading a Royalist force to relieve Charles I’s garrison at Oxford, was intercepted near Stow and driven into the Square, where many were killed or imprisoned.  Sir Jacob was forced to sit on a drum near the cross and surrender to the Parliamentarians. 

Today Stow-on-the-Wold is a thriving market town, although with a population of only 2,042 (2011 Census) it suggests a large village but at its heart it feels like a town, with a significant retail and business community.