The hill on which the ruins of Dinas Brân now stand was occupied in very early times. Four bronze axe heads found on the slopes, and the earthworks of a prehistoric hill fort around the ruins, point to ancient occupation of this natural stronghold.

Different authors ascribe different dates to the stone ruins that remain today. It seems most likely, however, that the castle was built by Gruffydd ap Madoc, Prince of Powys, sometime before his death in 1269.

The impressive stone fortress had a very short active life. In 1277, Henry de Lacy, Earl of Lincoln, lay siege to the castle and the Welsh, realising their hopeless cause, set fire to Dinas Brân.

The ruins of Dinas Brân have attracted tourists for over a century. At the end of the 19th century, a ‘camera obscura’ was built in the ruins to take advantage of the height of the hill and the views it afforded. In the middle of the 20th century there was even a shop on the summit, with the supplies carried up by donkey.

There are references to a bridge at Llangollen as far back as 1284 but the first stone bridge was built by John Trevor, the Bishop of St Asaph in 1345.

Rebuilding took place in 1656, and a stone with this date and the name of the stone mason, Rondle Reade, was found during a later bridge widening. The downstream side of the bridge is unaltered since the 15th century but the bridge has been widened twice on the upstream side.

In 1871 a census recorded 6585 people, 298 horses, 129 waggons, 92 carts and 79 cattle using this 8 foot wide bridge – sufficient evidence of chaos to justify the 1873 widening! In 1863 the symmetry of the arches had been spoilt by the addition of the railway arch and, during this work, pieces of tombstones with Latin inscriptions were found, thought to have come from Valle Crucis Abbey. The widening in 1968 was due to traffic congestion.

Llangollen’s bridge is regarded as one of the ‘Seven Wonders of Wales’:

“Pistyll Rhyadr and Wrexham Steeple,
Snowdon’s Mountain without its people,
Overton yew trees, St Winefride’s Wells,
Llangollen Bridge and Gresford bells”.

Eleanor Butler and Sarah Ponsonby moved into the small stone cottage of Pen y Maes in 1780, having run away from their families in Ireland two years previously.

Re-naming it Plas Newydd (New Hall) they made extensive improvements to the house and created new gardens. The ‘Ladies of Llangollen’ finally purchased the house in 1819 and went on to live there until their deaths in 1829 and 1831.

Over the years they became known for their eccentricity, preferring always to dress in dark riding habits, and played host to many famous people, including the Duke of Wellington, Sir Walter Scott and William Wordsworth.

After the death of the Ladies Plas Newydd was purchased by another two spinsters, Amelia Lolley and Charlotte Andrew, who attempted to emulate the Ladies’ lifestyle. In 1861 Plas Newydd was bought by Mrs Robina Couran who owned it for 15 years before selling it to Richard Lloyd Williams of Denbigh, who in turn sold it a few months later to General John Yorke. General Yorke added the black and white timbering, built a new west wing and opened the older rooms to the public. On his death in 1890 Plas Newydd was sold by auction and passed through a number of owners until it was bought by Llangollen Urban District Council in 1933 who opened it to the public.

In 1963 The Council demolished the east and west wings, leaving Plas Newydd the same size as when occupied by the Ladies. Today it is owned by Denbighshire County Council and continues to be open to the public.

Thomas Pennant, in his tour of 1773, refers to the House of Llantysilio as being the seat of Thomas Jones and in 1750 and again in 1792 we find that Thomas Jones of Llantysilio Hall was the Sheriff of Denbighshire. Pennant says that the “previous possessors were the Cupers or Cuppers – styled even so early as the time of Henry II the ancient Cuppers of the north”.

Thomas Cupper purchased the estate and built the original Hall at the beginning of the 18th century, and his daughter and sole heiress conveyed it to the Jones family by marriage with Thomas Jones, then of the county of Montgomery. Thomas Jones’ son and grandson, both also called Thomas, continued to own the estate, with the last Thomas Jones dying in 1820 leaving no will. The Hall, a “large brick building” passed to a Major Harrison who had proved his case to inherit and spent the next seven years fighting challenges to his claim.

In 1822 the housekeeper of the vicar of Oswestry dreamt that the will of Thomas Jones had been buried with him. Because of this dream a party of seven or eight people, including a lawyer and a surgeon, broke into the tomb and opened the coffin, although it would appear that the will was not found.

In 1873, Charles Frederick Beyer, who had purchased the Hall in 1867, constructed a new building of Ashlar stone and, in 1875, demolished the old Hall. He left the Hall to his godson, Sir Henry Beyer Robertson, and the house remained in the Robertson family until the late 20th century. During the Second World War Llantysilio Hall formed the Junior School for Moreton Hall School, catering for girls between the ages of 6 and 13.

Originally a small cottage called Braich y Gwynt, in 1865 Bryntysilio was bought by Sir Theodore and Lady Martin. The house was greatly enlarged, the work being completed in 1870. In 1889, Queen Victoria, a good friend of the Martins, took tea at Bryntysilio when she visited Llangollen.

Occupied by the military in the Second World War the house was afterwards restored, but much reduced in size by Mr Sydney Aston before being later sold to Walsall Education Authority as an outdoor education centre.

Ty'n Dwr Hall was built in the 1860s by John Dickin on land once belonging to the old Pengwern Hall estate. It has in the grounds what is considered to be the largest yew tree in Wales. The small cottage next to the Hall pre-dates it and was visited by George Borrow in 1854, when he remarked upon the nearby yew tree.

How long people have lived on the site of Ty'n Dwr is not clear, but a well in the cellar of the hall is much older and is said to date from Saxon times. Ty'n Dwr has for the last forty years or so been a youth hostel owned by the YHA.