Rudyard Kipling, Kim (1901) — The novel set partly in Shimla and along the Grand Trunk Road, drawing on Kipling's years in British India. The Shimla scenes — the social world of the Raj at summer, the espionage "Great Game" — are drawn from direct experience.
Ruskin Bond, The Room on the Roof (1956) — Bond grew up in Shimla and Mussoorie and has written about the hill stations of the Himalayas throughout his career. This, his first novel written at 17, captures the specific atmosphere of a hill station town with the authenticity of someone who spent his childhood in one.
Charles Allen, Plain Tales from the Raj (1975) — Oral history of the British Raj drawn from interviews with former colonial officers and their families, many of whom spent childhood summers in Shimla. The Shimla sections describe the hill station world from the inside.
Bill Aitken, Divining the Deccan (2006) — The British-born travel writer who spent his adult life in India writes about the Himalayan foothills with deep personal knowledge. His books on Himachal Pradesh provide the kind of textured, unhurried perspective that short-stay travel guides cannot.