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Combe Sydenham is associated with a legendary story concerning Sir Francis Drake, and another historical figure, George Sydenham, who has also become the subject of folklore.

Come Sydenham Hall was the home of the Sydenham family from the fourteen hundreds to the mid 18th century. Francis Drake married the daughter of George Sydenham in 1585, and the union has become embroiled in folklore. According to the traditional tale, Drake went away to sea on the Pelican for years leaving his fiancée on her own. After seven years had passed she grew tired of waiting, and went to remarry. Drake managed to hear of this by supernatural means while the Wedding guests were in Stogumber church waiting for the bride to walk down the aisle. Drake ran to the cannon and fired a canon ball that flew half way around the world, through the roof of the church and lodged in the church floor between the bride and groom. She took it as a sign from Drake that he was still alive and well, and abandoned the wedding, returning home to wait for her beloved.

In other versions of the tale George Sydenham tried to have his daughter married off to another man while he was away at sea. Sir Francis fired a cannonball from his ship thousands of miles away, which landed at Stogumber Church as the bride arrived.
A meteorite - the supposed cannonball - was kept in the village for many years.

Francis Drake - as with many famous historical figures - has become embroiled in many legends and traditions, some current during his lifetime, and others obviously added on later. In some parts of the West Country it was believed that he rode with the wild hunt, a tradition that was first attributed to Odin and other ancient gods.

The B3188 is also thought to be haunted by the white clad phantom of George Sydenham, who rides a headless white horse to the North of the road towards Monksilver, which may link him to an older figure of legend. Ruth L. Tongue in her book Somerset Folklore suggests the tradition may have started due to wicked deeds that George may have committed during life. It was a common belief that those who had done wrong in life would have to return to earth in a terrifying form to atone for their sins.