U Tirot Sing Syiem, the Hero of the Khasi hills, was born in 1802 in the Syimileh clan of the Nongkhlaw region of the Khasi hills. He is hailed for his warfare tactics, valor, and uncompromised control over the Khasi region against the British occupation.

In 1826, the British concluded the Treaty of Yandabo, which was signed nearly two years after the Anglo-Burmese war and gave them a stronghold over the Brahmaputra Valley. After this, the Surma Valley (in Assam and partly in Bangladesh) had also become a possession of the British. They wanted to link these two regions for easier transport and strategic purposes. For this, they had to construct a road through the Khasi Hills.

The story dates back to the 19th century when the Brahmaputra valley was finally accessible to the British. David Scott, a British agent had been searching for avenues to establish connectivity between Assam and Surma Valley in the hope that it would help trade flourish. The route would span a distance of about 230 km and would also cross Meghalaya. Meghalaya at that time was divided into smaller states and looked after by constitutionally chosen chiefs. One such chief was U Tirot Sing Syiem, who was the constitutional head of Nongkhlaw. He was a visionary who always worked towards the upliftment of his community. When he was told about the proposal, Tirot felt it would deeply benefit his community and hence immediately agreed to it.

Edward Gait in his book, The History of Assam, mentions that around early 1829, while the work was being carried out, a worker informed Tirot Singh that the British had ulterior motives with regard to the project and that they planned to levy taxes and subjugate them as soon as the project was completed. Tirot Sing called for a durbar with David Scott and others, wherein he raised his concerns and requested the British to vacate Nongkhlaw, to which the British never paid any attention. This enraged the Khasis as they felt cheated, for their trust had been broken. Tirot Sing led an attack on a small group of British officers and killed them. And the next four years are known as the Anglo-Khasi War, where Tirot Singh fought the British armies in the Khasi hills. It was a war of guns vs swords and arrows, in which Tirot Sing countered the colonial forces with his guerilla tactics.

Sustaining a bullet injury, Tirot Sing hid in a cave in the hills. However, he was captured by the British and finally forced to surrender to the British on 9 January 1833. He was deported to Dhaka and confined in the Dhaka Central Jail. He passed away on 17 July 1835 while still in confinement at Dhaka.

The Tirot Sing Caves in Meghalaya now are a major tourist attraction. Located in the Mairang region, a visit to the caves gives the tourists an experience of the war schemes of those times. These are the caves where Tirot Sing held secret meetings with his confidants. 17 July is commemorated as U Tirot Singh Day in Meghalaya.