Montserrat is discovered by Christopher Columbus in 1493, who names it after the Abbey of Montserrat. Montserrat becomes an English colony, annexed to Antigua, in 1632. It shares history with Antigua, but between 1664 and 1668 and between 1782 and 1784 it a occupied by France. With Antigua it is from 1833 until 1960 part of the Leeward Islands. In 1958 Montserrat gets internal self-government and becomes part of the British West Indies.

After the dissolution of the British West Indies in 1962, Montserrat becomes a separate British dependency, restyled into an associated state in 1967. Since 1960 William Henry Bramble of the Montserrat Labour Party (MLP) is chief minister. He is succeeded in 1970 by Percival Austin Bramble of the Progressive Democratic Party (PDP). Between 1978 and 1991 Montserrat is governed by the centre-right People's Liberation Movement (PLM) and its leader John Osborne. In 1991 Reuben Meade of the National Progressive Party (NPP) becomes chief minister after his party wins the elections. The NPP is defeated in the 1996 elections and the People's Progressive Alliance (PPA), successor of the PLM, and the Movement for National Reconstruction (MNR) form the government under chief minister Bertrand Osborne of the PPA. After the Soufrière volcanic eruption the independent David Brandt is appointed chief minister. After the elections of 2001 the New People's Liberation Movement, merger of the PPA and the MNR, wins a majority and John Osborne becomes chief minister again.