Although he is one of the most accomplished leaders and politicians in the world's history, Churchill also indulged in several hobbies. In fact, for Winston Churchill, hobbies were the ideal way for him to work through some of the most difficult political problems he was faced with, during his long and distinguished career.

Frequently turning to painting as a pastime, Winston Churchill was known for entering his study to paint for hours on end, with strict instructions to not disturb him. During the war, these painting sessions sometimes extended far into the night. Yet, he didn't come to this hobby early in life; he began painting when he was far into his adult years, at the age of 40.

An avid reader from the time he was 12, Winston found a deep, abiding love for literature, in all of its forms. Some of his most memorable quotes relate to his passion for the written word, instructing those who don't have time to read all of their books to "at any rate, handle them and, as it were, fondle them. Peer into them. Let them fall open where they will...make a voyage of discovery, taking soundings of uncharted seas." During his time in the military, while serving in India, he had an inordinate amount of free time – soldiers worked for seven months, with five months off. Much of this time he spent reading all the major literary works, with a nearly-insatiable appetite for stories and tales of adventure. He also spent a great deal of time studying Parliamentary history, reading the published debates, arguments, and issues of the time, systematically teaching himself to develop and support his own positions. This led to an unparalleled self-education, which far exceeded any of the 'formal' education he had been previously forced to suffer through.

Not one to just sit around indoors, another hobby Churchill indulged in was, oddly enough, bricklaying. Having bought his family home (Chartwell) in 1922, he spent the next two years totally rebuilding and expanding it, using his own two hands to construct several of the new buildings and the garden wall. He was so accomplished as a bricklayer, he got an apprentice card in the Amalgamated Union of Building Trade Workers. He also worked hard at landscaping, including planting huge gardens and entire orchards. He helped in the expansion of the lake, adding an island, water fall, goldfish ponds, and even a heated swimming pool (virtually unheard of at the time).

Winston was also a passionate animal lover, with his first love being horses. Thanks to his days in the cavalry, he was an accomplished horse rider and competitive polo player, which he participated in until his was well into his fifties. Around Chartwell, he kept the lakes filled with black swans and ducks, and the ponds filled with goldfish. He also raised cows and was extremely proud of his Middle White pigs. Inside the house (and out) cats and dogs had their run of the area. There are stories of staff members finding Churchill in bed, working, while a bird sat on his head, a cat on his ankles, and a dog laid next to him. Even during his time as Prime Minister, his pets were allowed to wander freely, even finding their way into official meetings or meals.