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A Neolithic settlement situated south of the river was excavated in 2001 finding evidence of a timber building 25 metres (80 ft) in length along with Neolithic pottery. The Auchenlaich Cairn, a Neolithic chambered cairn which at 322 metres (1,056 ft) in length is the longest in Britain, is situated near Keltie Bridge just east of Callander. The remains of an ancient hillfort can be seen at Dunmore overlooking Loch Venachar, near Kilmahog. This fort was likely a large defended structure visible from some distance and excavations have revealed a well and signs of vitrified stonework. Nearby, the remains of Roman ramparts constructed during the campaigns of Agricola in the first century AD are visible at Bochastle Farm.
Saint Kessog, a disciple of Columba of Iona, preached and taught in this area in the early sixth century. A small mound by the River Teith is named in pseudo-Gaelic as "Tom na Chessaig", meaning "the Hill of Kessog". This man-made mound is circular with a level top approximately 10 metres (30 ft) in diameter. It is reputed to have been constructed as a memorial to the Saint or even to be the remains of Callander's original church (situated close to the old graveyard). The structure has actually been identified as a medieval motte, although no excavation has confirmed this. Historians record that an annual market called "Feill ma Chessaig" (festival of Kessog) was held here until the early 19th century.
A medieval tower house, Callander Castle, once stood south of the river, which is said to have been "a square tower of considerable height". This belonged to the Livingstons of Callendar House near Falkirk. The only remains of the castle are some masonry and a possible datestone inscribed 1596, which is now incorporated within the old St Kessog's Manse on the same site.
In 1645, during the campaigns of Montrose, a battle was fought at Callander between the Campbells of Argyll and the Atholl men. The Campbells were harassing the McGregors and the McNabs for their allegiance to Montrose. While besieging Castle Ample, the news came of the advance of 700 Atholl men under Inchbrakie. A retreat was made southwards, but, as the Campbells were crossing a ford to the east of the village of Callander, they were overtaken and compelled to give battle. Inchbrakie, advancing part of his force to attack the defenders, quietly marched another detachment towards a ford higher up near the present bridge. A crossing was soon effected, and the Campbells, being unexpectedly attacked on the rear, broke and fled, leaving eighty of their men dead on the field.
Although it is not known when the area was first settled, Callander is mentioned in parish records since at least the 15th century. The Medieval Parish of Callander was a patchwork of estates, settlements and farms and some of these survive in the present street names, such as Murdiestoun, Balgibbon and East Mains. The area around Callander was cleared for sheep before 1800 as part of the early phases of the Highland Clearances.
Scottish Gaelic was once widely spoken. In 1803, William Wordsworth and his sister, Dorothy, visited Callander and the Trossachs and recorded everyday encounters with Gaelic language and culture. In the 1840s sermons were delivered in both Gaelic and English, and Gaelic was taught in at least two schools in the area. By the 1880s most locals were speaking a mixture of Gaelic, Scots and English. In the 1900s, Celtic scholar, William J. Watson, documented, "four Gaelic-speaking men born near Callander, two of whom were over 80 and had excellent knowledge of the place-names." However, one 19th century writer (Alexander MacGibbon) took objection to the local dialect, stating, "The true Gaelic is a noble language, worthy of the fire of Ossian, and wonderfully adapted to the genius of a warlike nation; but the contemptible language of the people about Callander, and to the east, is quite incapable of communicating a noble idea."
Post Office
Callander was served by rail from 1 July 1858 as the terminus of a branch line from Dunblane. A second Callander railway station was opened about 1⁄2 mile (800 m) to the west, behind the Dreadnought Hotel, on 1 June 1870 when the railway was extended to Killin en route to Oban, and closed on 5 November 1965. Sections of this former Callander and Oban Railway line, between Callander and Strathyre and between Balquhidder and Killin Junction, are now part of the National Cycle Network (route 7) and the Rob Roy Way. Track from the dismantled Callander and Oban Railway was used in the construction of the transit system for the 1968 Summer Olympics in Mexico City.
The noted Scottish landscape artist Archibald Kay RSW RSA chose Callander as his home from 1904 and he became a noted resident of the town. A member of the Glasgow Art Club, The Paisley Art Institute and a close associate of fellow artist George Houston, Kay painted all around the River Leny and the hills of the Trossachs National Park and Kay is noted especially for his views of Ben Ledi overlooking Callander. Elected a member of the Scottish Royal Society of Arts, Kay was elected a member of the school board for McLaren High School in 1911 and was commissioned by Callander town council to design the war memorial to honour the fallen from the town and this was erected in Ancaster Square. Kay died in 1935 and is buried in Callander alongside his twelve-year-old son Archie, who drowned in a boating accident in 1907, and Archibald Kay's cousin George Whitelaw who also drowned trying to save him. Kay's second wife Mary also rests in the impressive Georgian style monument in the Stirling Road Cemetery.
