That the Upper Tweed valley had been the route of a Pilgrims Way is evidenced by the site of what must have been an imposing way marker on the Dumfriesshire border at the south end of the parish. For more about this see the Tweeds Cross page. This cross was beside what was known as the Old Edinburgh Road. There was a probable cross/way marker at the site of the Crook Inn that gave the Inn its name see origins of Crook name page. There would also have been a way marker at the ford over the River Tweed at the Tweedsmuir Kirk Mound (Chapel Knowe) site.
The Pilgrim's Way would be the route for pilgrims heading north from England/Wales to Glasgow, also to Stobo but more importantly to the Queensferry - the ferry crossing of the River Forth to continue to St. Andrews. The new cable-stayed bridge presently being constructed at this location, due for opening in 2016, has inspirationally been named The Queensferry Crossing.
It is probable that St. Mungo (St. Kentigern) passed this way when he walked from North Wales to Glasgow. There are plans to make a long distance walkway (St. Kentigerns Way) following the route he probably took. From Moffat northwards the historians planning the route suggest that the route followed the track of the old roman road that passed Ericstane and went north-west. This route would bypass the village of Tweedsmuir and the Crook Inn. However the new walkway route maybe altered to take in Tweedsmuir.
It is probable that the seventh century Cuthbert later Saint Cuthbert from the Iona community at Old Melrose resided in the Upper Tweed area for a while and had an existing chapel at Kingledores dedicated to him in the thirteenth century.
Apart from the Pilgrim's Way markers there are three ancient chapel sites in the Parish indicating an expansion in Christianity in the area in the twelth/thirteenth century era or possibly even earlier as the result of the influence on the spread of the doctrines of the Church of Rome by Queen Margaret (1045-1093) - later St. Margaret - second wife of Malcolm III Canmore (1058-1093), King of Scots. This doctrine was opposed to that of the earlier Celtic Churches. Queen Margaret, of course, is the Queen in Queensferry who provided the ferry service for pilgrims across the River Forth.
The three chapel sites are:-
a) Chapel Knowe.
b) Chapel Kingledores. During the reign of Alexander II (1214-1244) a charter by Sir Simon Fraser of Oliver gave a right of way through the lands of of Mospennoe (Mossfennan) to reach their lands of Hopecarthen on the other side of the Tweed This charter allowed the access of horses/oxen (latin - averiis) cattle and carriages (latin - caraigia). In a further charter granted a few years later another Simon Fraser confirmed to the Church in Melrose... the whole land of South Kinglidores, together with the Chapel of St. Cuthbert of Kinglidoris, and also the land of Hopecarthen, to be possessed by them as freely as they had enjoyed the same under Sir Simon Fraser, his disceased father. It is of interest that even to the present day access to Stanhope /Hopecarton is still through Mossfennan lands.
The Melrose Monks would not have named the Chapel of St. Cuthbert themselves, they would have inherited the name along with the Chapel. There is regrettably no vestige remaining of the this Chapel at Kingledores but we do know that it was in South Kingledores ie south of the Kingledores burn and is shown on Blaeu's map of 1654 - see Origines of Crook name page. This location is confirmed by the Royal Commission for the Ancient Monuments for Scotland (RCAHMS) and recorded on their online archive Canmore as ID 49765
Around 1200 it is recorded that there was hermit monk named Crispin who resided at Kingledores. St Cuthbert is not mentioned at this time so the chapel must have been dedicated to that Saint between 1200 and the arrival of the Cistercian Monks from Melrose Abbey later in the thirteenth century. Glenholm Kirk and also Drumelzier were also dedicated to St. Cuthbert around this time.
The dedication to St Cuthbert of the chapel sites of Kingledores, Glenholm and Drumelzier is a very strong indication that he had a strong connection with the area.
St. Cuthbert lived in the seventh century and it was at Old Melrose where a community of Monks from Iona had established themselves in their drive to spread Christianity. Cuthbert had not come from Iona but was local to Old Melrose. At this time the area now known as the Scottish Borders was part of the ancient Kingdom of Northumbria. St Cuthbert is more associated with Lindisfarne and Durham but there is no doubt that he was of local to Old Melrose origin.
The Monks from Iona chose a site on the River Tweed as a base from which Christianity could be spread to the Tweed valleys. This site was Old Melrose which was on the north side of the Tweed a few miles East of the present day site of Melrose Abbey. The site had been revered by the ancients, it was on a loop of the river and was surrounded on three sides by water with access by a ford that they named Monksford. They also named a crossing of the River Teviot as Abbotsford.
The Monks from Old Melrose, particularly Cuthbert began to travel widely, preaching, teaching visiting and living with the "rough hill folk". Cuthbert sometimes went on horseback, more often on foot. Bede tells us that it was a labour of love to him and that he made a point of searching out " those steep rugged places in the hills which other preachers dreaded to visit because of their poverty and squalor". Did Cuthbert reach Upper Tweed and his good works were remembered resulting in existing chapels in the area being dedicated to him after he was sanctified? Why would these chapels be dedicated to him otherwise?
Armstrong was keen on vestiges of chapels, wayside crosses etc but he makes no mention of Chapel Kingledores in his Peeblesshire narrative. The site became a Tweedie residence as it is recorded that a David Tweedie married to Margaret Hunter had at least three children born at Chapel Kingdledores, namely Margaret b 07-03-1670, Besse b 27-02-1672 and Agnes b 04-06-1678. However by the first census of 1841 Chapel Kingledores is not recorded.
c) Fruid Chapel. Captain Armstrong writing in 1775 about Fruid states that there were faint vestiges of a chapel and burial ground. The (RCAHMS) in their survey of sites in Peeblesshire in 1959/60 could not identify the chapel or burial sites. There is a Chapel Burn which flowed through the site of Hawkshaw Farm near Hawkshaw Castle. However further up the Fruid Valley there is a Priesthope Burn a tributary of the Carterhope Burn which I think is the more likely site of the chapel and burial ground. Andrew Lorimer in his book Life and Times in the Upper Tweed Valley concurred with this view. The Fruid Valley was flooded and covered Hawkshaw farm to form the Fruid Reservoir but both Andrew Lorimer and the RCAHMS walked the valley prior to this event.
As mentioned above I believe that the site of the chapel was close to the present day Priesthope Burn/Carterhope and also adjacent to the ancient castle of the Frasers of Fruid - RCAHMS Canmore ID 49742 - that was on or near Strawberry Hill.