The earliest inhabitants of Westmoreland were the
Arawak and
Ciboney peoples. The Ciboney were first to arrive, from the coast of
South America, around 500 BC. Known as "cave dwellers", they lived along the cliffs of
Negril. The
labyrinth of caves and passageways beneath what is now the
Xtabi Hotel in Negril are one of the first known settlements of Ciboney Indians in Jamaica.
Christopher Columbus stopped at what became Westmoreland on his second voyage when he landed in Jamaica. One of the first
Spanish settlements was also built at present-day
Bluefields in this parish. The English took over the island from Spanish rule in 1655. Colonists named the parish
Westmoreland in 1703, for it was the most westerly point of the island. In 1730,
Savanna-la-Mar, a coastal port, was designated to replace Banbury as the capital of the parish. A fort was built in the 1700s to defend the port against pirates. Today, it is one of the historic sites of the parish. In the mid-18th century, Westmoreland was, acre for acre, one of the most profitable territories, not only in Jamaica, but throughout the British empire. The plains of Westmoreland were densely populated with sugar plantations, and by the time of
Tacky's War, Westmoreland had about 15,000 slaves labouring on more than 60 sugar plantations, many of them owned by leading men of the island, such as
William Beckford and
Arthur Forrest. The name
Westmoreland appears to stem from Dr
John Drummond (1744–1804), who had several plantations on the island (foremost being the Drummond Estate) and vast lands at
Savanna-la-Mar, which had been owned by his parents. He was surgeon to the
Westmoreland Regiment of Foot from 1784. This British regiment was officially on the island from 1802 to 1813, but the name appears to pre-date this, for John Drummond refers to his "Westmoreland estate" in his will of 1793. In 1938,
riots at the Frome
sugar estate changed the course of Jamaica's history. In the wake of these riots, the legislature passed legislation for universal adult
suffrage in 1944, as well as a new
constitution, which was approved by the Crown. This put Jamaica on the road to
self-government and eventually,
independence. The two national heroes, Sir
Alexander Bustamante and
Norman Washington Manley, emerged as political leaders during this time. On 28 October 2025,
Hurricane Melissa made landfall near New Hope in the Parish at its peak intensity as a Category 5 hurricane, making it by far the strongest hurricane to ever strike the island (surpassing
Hurricane Gilbert which made landfall in eastern Jamaica as a low-end Category 4 hurricane in 1988), tying the
1935 Labor Day hurricane as the third-most-intense Atlantic hurricane on record. ==Geography==