The region in which Annandale is located was first documented in 1834, in the East Indian United Service Journal. When British officers saw the area for the first time, they found it similar to the Annandale valley in Dumfriesshire or County of Dumfries in Scotland, and decided to name it after the Scottish location because most of the officers hailed from the original Annandale. According to another story, Charles Pratt Kennedy, the political agent of the British government who was assigned to find a suitable place in India for selecting the Summer Capital, came to Shimla hills in 1822. He was so impressed by the beauty of the dale that he named it after "Anna" his lady love back in England. It is perhaps for this reason, that it has been spelt as both 'Annandale' and 'Annadale' in documents pertaining to Shimla.
Annadale was first used by East India Company and then the British Raj, which is why natives originally called it "Company Ka Baag". It was a place of enjoyment and entertainment for the British, offering fancy dress shows, picnics, and birthday celebrations. Every year a National Championship of Polo was organised there. Cultural and social festivals were organised there including Gymkhana, fete champetre and sports such as polo and cricket. Under the British Army, the grounds were also used for training and parades. A funfair was organised in September 1833 to raise funds for setting up a school at Sabathu for native girls. In 1839, the first Fancy fair was organised there. The Durand Football Tournament was started in 1888 in Annadale by Mortimer Durand. It was interrupted during World War 1 and World War 2. The venue was shifted to Delhi in 1940. British officers appreciated the nature and scenic charm of the site and protected it from disturbance by grotesque structures. During the 1924 gymkhana, a shed was built without proper permission of the municipal committee, who later questioned it. The Annadale Gymkhana committee, in its explanation, replied, "The genesis of this shed was the desire of one of the Indian members of the club for the purdah ladies who then can view the sports from the shed."
Gymkhana, polo, football, hockey, cricket matches, and other cultural and social festivals were organised in Annadale after independence. Dussehra was the main event organised, attracting people from the city, but in 1972 a clash between army and police created enmity between the military and civil administration. After this incidence, the event was shifted to Jakhoo Temple. Another major event was the 1971 plenary session of the All India Congress Committee. In addition, a national women's field hockey championship was also organised there. A Yajna was organised by Gayatri Parivar in 1994.
Annadale got in controversy during 2005 to 2012, when Himachal Pradesh Government wanted to make an International Cricket Stadium here, but Indian Army refused this by saying that it would damage the scenic charm and nature of the valley and because of all this the situation became a bit controversial. In 2011 government made an idea to ask the people of Shimla about this decision, in which the board was placed on The Ridge, on which the people who support this concept had to sign on the board. Most people supported this by signing on the board, but still government had to accept the Army's demand by cancelling the plan, then the plan was shifted to Dharamshala.
Education
Annadale has three colleges i.e. Modern Nursing College, Shimla Nursing College & B. Ed College. It has three government schools i.e. Govt. High School, Govt. Primary School, Annadale & Gawai Primary School.
