The Domesday Book of 1086 refers to Sidmouth as Sedemuda, which means “mouth of the Sid.” It started off as a fishing community, like so many others.

Sidmouth had grown to be a market town comparable to Sidbury by the 1200s, bringing in more money for the abbot of Mont-Saint-Michel than Otterton. Sidmouth had a parish church by this period, since the Otterton Cartulary mentions a bequest of 30 acres of land to Guilielmas, the vicar of Sidmouth, as a glebe, and foundations dating from that time were discovered during the rebuilding of the parish church in 2009. The annual fair was held on St Giles’ feast day, September 1st, so it’s possible that the chapel was already dedicated to him. According to one of the many blue plaques located around Sidmouth, a chapel dedicated to St Peter was erected near the church sometime before 1322, and the surviving wall is now part of Dukes Hotel.

Sidmouth prospered from the wine trade in the 14th century, and King Henry V transferred the manor of Otterton from Mont-Saint-Michel to Syon Abbey as part of the manor of Otterton. During the dissolution of the monasteries, King Henry VIII confiscated it again and sold it, following which it passed through numerous hands until being bought by the Mainwaring baronets, whose family furnished two of the vicars of Sidmouth parish.

Although attempts to build a harbour have been attempted, none have proven successful. The town’s expansion as a port was hampered by a lack of cover in the bay. Despite this, a section of the town is known as ‘Port Royal,’ which is possibly owing to the town providing King Edward III with two ships and 67 troops to assault Calais during the Hundred Years’ War. The most intense effort was in the 1830s on the west side of the seashore, which involved the building of the Sidmouth Harbour Railway down the coast and into a tunnel through the cliffs to the east, which would have delivered stone from Hook Ebb. Today, just a few remains of the railway and tunnel remain.

According to one of the Sid Vale Association Blue Plaques, a fort was erected on the area of the beachfront known as ‘Fortfield’, which is now the cricket ground, in 1628, owing to fear of a French invasion or naval attack.

Another of the Sid Vale Association’s Blue Plaques states that the Old Ship bar (now a Costa Coffee) in Sidmouth has been a tavern since the 1400s and was frequented by smugglers. Jack Rattenbury, who was born in Beer, Devon, and was known to consort with the Mutter family of Ladram Bay (for whom Mutter’s Moor on Peak Hill overlooking Sidmouth is called), operated in the region.