The formation of the regiment was prompted by the expansion of the army as a result of the commencement of the Seven Years' War. On 25 August 1756 it was ordered that a number of existing regiments should raise a second battalion; among those chosen was the 19th Regiment of Foot. The 2nd Battalion of the 19th Regiment of Foot was formed on 10 December 1756 and renumbered as the 66th Regiment of Foot on 21 April 1758. The regiment was posted to Jamaica in 1764 and then returned home in 1773. The regiment was given a county designation as the 66th Regiment of Foot in 1782. In April 1785 the regiment embarked for the West Indies and was garrisoned at Saint Vincent before leaving for Gibraltar in January 1793.
The regiment left Saint Helena in May 1821 following Napoleon's death. It was deployed to Canada in August 1827 before returning home in October 1840. It was sent to Gibraltar in July 1845 before returning to the West Indies in 1848. It returned to Canada in 1851 and returned home in 1854. In March 1857 it was sent to India to help suppress the Indian Rebellion. It returned to England in March 1865 but went back to India in February 1870.
Second Anglo-Afghan War
The regiment was deployed to Afghanistan in early 1880 and took part in the Battle of Maiwand in July 1880 where the British forces were routed and most of the regiment was caught up in the rout. Some 140 of them made a stand at the Mundabad Ravine, which ran along the south side of the battlefield, but were forced back with heavy losses. Eventually 56 survivors made it to the shelter of a walled garden and made a further stand. Eventually the 56 were whittled down to only 11 men—two officers and nine other ranks. An Afghan artillery officer described their end: Officers who died in the action included: Lieutenant-Colonel James Galbraith, Captain Ernest Stephen Garratt, Captain William Hamilton M'Math, Captain Francis James Cullen, Captain Walter Roberts, Lieutenant Maurice Edward Rayner, Lieutenant Richard Trevor Chute, Second Lieutenant Arthur Honywood, Second Lieutenant Walter Rice Olivey and Second Lieutenant Harry James Outram Barr. A subscription led to two memorials in Reading: a window in St Mary's Church, and a large memorial sculpture, the Maiwand Lion, erected in 1886 in Forbury Gardens. The regiment also saw action at the Battle of Kandahar in September 1880.
Amalgamation
As part of the Cardwell Reforms of the 1870s, where single-battalion regiments were linked together to share a single depot and recruiting district in the United Kingdom, the 66th was linked with the 49th Regiment of Foot, and assigned to district no. 41 at Brock Barracks in Reading. On 1 July 1881 the Childers Reforms came into effect and the regiment amalgamated with the 49th Regiment of Foot to form the Princess Charlotte of Wales's.
Legacy
wrote of the Battle of Maiwand in his poem The Last Berkshire Eleven: The Heroes of Maiwand, which includes mention of Bobbie, the regimental pet dog, who survived the battle: Dr. John H. Watson, fictional narrator of Sir Arthur Conan Doyle's Sherlock Holmes stories, was wounded while attached to the regiment at the 1880 Battle of Maiwand. He was on attachment from his own regiment, the 5th Regiment of Foot.