East Ayrshire has many places of historic interest.
Remains such as the Dragon stone in Darvel and cup and ring markings near the Ballochmyle viaduct in Mauchline are evidence of early occupation of East Ayrshire, but the first permanent settlements probably date from the expansion of Christianity after St Ninian established his church at Whithorn near the Solway Coast in 397.
There are many towers and castles dating from the 13th to 15th centuries, when the barons were at the height of their military and political powers. Many were decisively involved in national affairs, in particular resistance to Edward I's advances on Scotland.
William Wallace had many connections with the local area. These include his family's castle at Riccarton (Kilmarnock) and his ambush of an English convoy at Loudoun Hill in 1297. Legends also associate him with local sites such as Lockhart's Tower, Galston, which was largely rebuilt later in the middle ages and is now referred to as Barr Castle, from where he is said to have made a daring escape. He gathered men at Mauchline Muir before the ambush at Loudoun Hill. Robert I (the Bruce) was also active in the area, and in 1307 won a battle against Edward I's forces at Loudoun Hill.
Mid - late 17th century
The Covenanters were particularly active in this part of Scotland, promoting the National Covenant, a backlash against the enforcement of particular forms of religious observance by James II and then Charles II. As the King attempted to enforce his requirements, "deceit, treachery, arrogance, atrocities, courage, faith, devotion, loyalty and derring-do were all there".
Many Covenanters died for their beliefs. There are many sites and monuments in East Ayrshire, particularly at Fenwick Kirk Yard, the Laigh Kirk in Kilmarnock, Galston Kirk Yard, Loudoun Old Parish Kirk near Galston, Newmilns Keep and Kirkyard, Threepwood near Galston, Lochgoyne farm on the moors above Fenwick, Priesthill farm near Muirkirk, Mauchline, Sorn, Cumnock and Airdsmoss near Cumnock.
Mauchline was the site of the Battle of Mauchline Muir in 1648 between Covenanters and Royalists. A Covenanters Memorial in Loan Green commemorates five martyrs hanged there in 1685. 'Covenanter stones' commemorating many deaths and summary executions, can be found throughout the area.
This period saw the establishment of 'Burghs of Barony' and many towns received Charters - Newmilns in 1491, Auchinleck in 1507, Cumnock in 1509, Kilmarnock in 1592 and Riccarton in 1638. Many towns flourished and prospered after the granting of their Charters, with lively trade in agriculture, livestock and textiles.
18th - 19th centuries
By the 18th century textile production dominated industrial expansion. Muslin, cotton, blankets, carpets and woollen goods were produced in Kilmarnock, while Stewarton was famous for its bonnets. The Irvine Valley was renowned for its specialised lace industry.
The 18th and 19th centuries saw East Ayrshire becoming one of the industrial powerhouses of the growing British Empire. In addition to a textile industry of world significance in the Irvine Valley, coal mining was important across the area. Iron making developed at Dunaskin in the Doon Valley and important industry also grew in many parts of East Ayrshire, such as the making of railway rolling stock in Kilmarnock which was exported across the world. The world's oldest railway viaduct was built at Laigh Milton, Gatehead near Kilmarnock.