Another great hurricane hits the island, this time taking aim on Plymouth and the south of the island. Much of the damage from the hurricane of '24 had been repaired, with the island (relatively) prosperous. The cotton pests were under control and a good harvest was expected. Plans were afoot to generate electricity, make ice, and publish a new newspaper (there had been a couple of unsuccessful ones before). The hurricane put the brakes on all of these wonderful plans.

A devastating hurricane makes a direct hit on the east and north of the island. The hurricane hit about midnight on 28 August without warning, when nearly everyone was asleep. While sparing Plymouth and the south for the most part, it took only 2 hours, 1 AM to 3 AM, to devastate the north of the island.

When the hurricane reached Montserrat on August 7th, 1899, the area of the storm had increased, the barometer was almost two inches lower (than on August 3.), having fallen to 27.45 inches, the wind blew with hurricane force, causing immense damage and loss of life, and the rainfall was excessive (Monthly Weather Review, Oct.1900). The pier was blown away and the material newly laid in for its extension gone to sea. The courthouse and a school are standing and crowded with homeless women and children. Not a church or parsonage is standing in the island.