It is not known when people first began living in the area which became Totnes, but the natural setting – a long hill sloping down to the tidal head of the River Dart, surrounded on three sides by extensive marshes and protected by higher hills all around – was ideal for human settlement. What is now the main street was originally part of an ancient track, probably Bronze Age (4,500 to 2,800 years ago), which crossed the river by a ford and continued on towards Cornwall.

There could have been small communities on and around the hill during the Roman period, but the continuous existence and identity of Totnes begins in the late 9th or early 10th century, when it was built as a fortified, hilltop town to defend the area from Viking attacks.

Devon was by this time part of the Anglo Saxon kingdom of Wessex, which from the late 8th century became subject to raids by the seaborne warriors from the coasts of Norway and Denmark whom we know today as Vikings. By the end of the following century the Vikings were permanently established on English soil, and Wessex was fighting to survive. Totnes was founded either by King Alfred or his son Edward as part of a highly organised system of ‘burhs’ or fortified places where people could seek protection. Some burhs were old Roman cities like Exeter, some were ancient hill forts brought back into use and others, like Totnes, were newly built. The burh enclosed the old road and encircled the hilltop.

We do not know if the Vikings ever actually came to Totnes, but in 1001 they burnt Kingsteignton, which occupied a similar position on the Teign estuary, and went on to attack Exeter. However, when the Danish king Knut (Canute) was crowned king of England in 1016, and the country became part of an Anglo Danish empire, fighting was replaced by trade, which continued after the Norman Conquest in 1066. Coins minted in Totnes have been found extensively in Scandinavia, showing the importance of the town at this time. Many can be seen in Totnes Museum.

A thousand years later, trading links between Totnes and the Scandinavian and other Baltic countries resumed, when in 1890 the firm of F.J.Reeves and Sons started to import timber. The business flourished and in the 1960s Baltic Wharf was built to cater for the ships which regularly visited the town, though this ceased in the 1990s.

After the Normans arrived, the town began to develop outside the original walled area, and the long street stretching down to the river came into existence. The lower parts of the town were still marshy and subject to flooding. Reclamation began in the 13th century when a dam was built, and the area behind it became known as ‘Weirland’ (now Warland). Nearby was a small area known in early documents as ‘picklemore.’ It is thought that this indicated an insignificant, trifling amount of not very valuable land: ‘moor’ was often used to denote low-lying as well as highland areas, and this land was clearly ‘not worth a pickle.’ Others suggest it meant a small ‘prick’ of land on the edge of the marsh and river: ‘prick le mer street’ occurs in a deed of 1642. ‘Tucklemore’ appears much more recently, and the current form is probably only 19th century.