After the Romans withdrew from Wales, the kingdom of Gwent emerged, and, according to tradition, one of their 6th century kings, Tewdrig, abdicated to become a hermit in Tintern.

Tintern Abbey was founded beside the river by Walter de Clare on 9 May 1131, during the reign of King Henry I.

During some of this period the area was contested between the Welsh and English, the closest battle being won in 1404 by Owain Glyndŵr, at Craig y Dorth near Monmouth.

It has been suggested that the monks or lay brethren of Tintern Abbey exploited the woodlands and river power for operating iron forges, but evidence of this is lacking.

This was used to produce a wide variety of goods: cards for the woollen industry, nails, pins, knitting needles and fish hooks.

In 1878 a new company leased the site to manufacture tinplate, but by 1895 it was reported as closed and only some ruins, associated ponds, leats and culverts are now visible.

[11] In March 2021, discovery of an underground structure paralleling Angiddy Brook was initially thought to be a "secret medieval tunnel system".

[12][13] Subsequent investigation identified the structure as an original leat system for one of the "missing" mills associated with Tintern Abbey.

[14] By the late 18th century, tourism had started in the Wye Valley, with many visitors travelling on the river to see the abbey and other "picturesque" sites in the area.

[17] The grade II listed Wild Hare Inn, formerly the Royal George Hotel, was established soon after the turnpike road opened.

[21] St Mary's reredos has been transferred to nearby St Michael's Church for safe-keeping, but interesting architectural features include the following: medieval stonework concentrated at the east end; 14th and 15th century tracery; undated but pre-Victorian stonework such as the stoup, niche, piscina and unusual saddleback stone-tiled tower.

Also Grade II and listed in the surrounding area: the neoclassical monument to J S Brown (d. 1840),[22] a rare 18th or 19th century pyramid tomb,[23] an 18th or 19th century Neoclassical or Baroque sarcophagus tomb of Richard White (d. 1765),[24] and the revetment wall and adjoining paved road leading up to the churchyard.

[27] The former public house, The Moon and Sixpence, was originally known as the Mason's Arms, but changed its name in 1948 following a visit by Somerset Maugham, author of the 1919 novel of the same name.

It was substantially rebuilt in 1846 (although pictorial records suggest it was relatively similar in appearance before and after the rebuilding) and has remained largely unchanged since.