It has been suggested that the name Winkleigh comes from the Old English words Wincel and Leah, meaning a clearing near some nook or corner. But those who gave it a name were not the first settlers, for tantalising records of Bronze Age finds suggest it was a village way back in prehistory. Very little is known about the parish before the Saxon invasion, then Winkleigh was the seat of the Saxon Earls of Gloucester. The last of these was Brictric who lost his lands to Matilda the wife of William the Conqueror.

Winkleigh is mentioned in the Domesday Book as Wincheleia, it paid £30 in coinage as tax. This was a lot of money in 1086, Winkleigh was a very wealthy parish, Okehampton was worth only £10, Chulmleigh £13 and North Tawton £15. It is also recorded that in the manor there is a park for wild beasts, belonging to the King.

In the village are two large mounds, the remains of 12th century castles; Winkleigh is the only village in Devon with two such remains. They could have been the bases for the two warring families who lived here in the time of the civil war, when Stephen and Matilda were rivals for the throne. Court castle, the larger of the two, belonged to Keynes family and Croft, where the village hall stands, the Tracey family.

In the 13th century the village continued to prosper, mainly from sheep and wool products. A weekly market and three annual fairs were granted by a charter dated 1262. The small hamlet of Hollocombe was also raised in status at this time, and had a fair charter of its own in 1260, and later in 1361 the manor of Hollocombe was given grant of free warren and fortification of the manor, making it into a very grand place indeed.

During the 14th century, Winkleigh was badly affected by the Black Death, so many people died that in 1349 there was not a single house paying rent in the town. Winkleigh slowly recovered from the devastation of the plague and by the 17th century was involved in matters of national importance, when another civil war reached Devon. At this time the owner of the manor of Hollocombe Sir Bartholomew Gidley, fought on the side of the king, and was decorated for
his loyalty. Winkleigh appears to have come through these times fairly unscathed and once again returned to its peaceful way of life.

The next major change to come to Winkleigh was the industrial revolution; this affected all walks of life tremendously, from agriculture to the home. To commemorate the reform bill of 1832, a pump was erected in Winkleigh square, this granite obelisk has the names of the men involved recorded on it.

Just over a hundred years later more changes came to Winkleigh in the shape of the Airfield that was built for the Second World War. Much farmland was taken up not only by the airfield itself but also by its many dispersed sites; these housed the wartime personnel from all over the world giving the parish a
completely different outlook on life.