The name Tenterden is derived from the Old English Tenet Waraden", meaning a den or forest clearing in the forest which belonged to the men of Thanet.
The first record of dwellings in Tenterden can be found in a charter which mentions Heronden, the town, began to grow from the 14th century around the wool industry. Unlike other such centres in the Weald it had the advantage of access to the sea. Much of what is now Romney Marsh was under water, and ships docked at Smallhythe. Timber from the Wealden forests was used to construct ships, and in 1449 Tenterden was incorporated into the Confederation of Cinque Ports as a limb of Rye. Ships built in the town were then used to help Rye fulfil its quota for the Crown.
A school was in existence here in 1521; later (in 1666) it was referred to as a grammar school.