James Ronald Webster Day

The date of James Ronald Webster Day is fixed to his biological birthday, March 2nd. However, in accordance with Anguillian labor laws and public holiday traditions, if March 2nd falls on a Saturday or Sunday, the following Monday is typically declared a public holiday to ensure the workforce and students can fully participate in the commemorative activities. For 2026, the holiday falls perfectly on a Monday, providing a seamless transition from the weekend into a day of national reflection.

The Life and Legacy of James Ronald Webster

To understand why this day is so vital to Anguilla, one must understand the man behind the name. James Ronald Webster was born on March 2, 1926, into a large family of sixteen siblings. Life in Anguilla during the early 20th century was incredibly difficult. The island suffered from a lack of natural resources, frequent droughts, and a total absence of basic infrastructure like paved roads, electricity, or running water. Like many young Anguillian men of his generation, Webster had to seek opportunities abroad to support his family.

At the age of 17, he traveled to Saint Martin, where he found work on a dairy farm and in a factory. His work ethic was legendary. Over nearly thirty years, he rose through the ranks, eventually becoming so trusted by the farm's owners—a Dutch couple—that he inherited their entire estate upon their passing. This inheritance provided him with the financial independence that would later prove crucial in funding the early stages of the Anguilla Revolution.

When Webster returned to Anguilla in 1960, he was shocked by the state of his home island. While other Caribbean territories were seeing modernization, Anguilla remained frozen in time. The island was then part of the Saint Christopher-Nevis-Anguilla Federation, governed from Saint Kitts. It became increasingly clear to Webster and his contemporaries that the central government in Saint Kitts was systematically diverting development funds and international aid intended for Anguilla to its own projects. Anguillians were being taxed without receiving benefits, and their political voice was being smothered.

The Revolution of 1967

The frustration reached a breaking point in 1967. James Ronald Webster emerged as the natural leader of the movement to break away from the federation. He wasn't just a political figure; he was a man of action. Under his leadership, the Anguillian people took the radical step of expelling the Saint Kitts police force from the island in May 1967.

This was a David vs. Goliath story. A small island of goat herders and fishermen was defying a regional government and, by extension, the British Crown. Webster’s integrity was his greatest asset. He managed to unite the various factions on the island, convincing them that they were better off standing alone than remaining in an oppressive union. His leadership led to the "Republic of Anguilla" (1967-1969), during which the island managed its own affairs despite the lack of international recognition.

Even when the British launched "Operation Sheepskin" in 1969—sending paratroopers and marines to "invade" the island—Webster handled the situation with a calm dignity that won over the British soldiers and the international press. He used the global spotlight to highlight the neglect Anguilla had suffered, eventually forcing the British government to grant Anguilla a separate administration, which eventually led to its status as a British Overseas Territory, forever severed from Saint Kitts.

Political Career and Governance

Following the success of the revolution, Webster served as the island's Chief Minister on three separate occasions:

1. February 1976 to February 1977
2. May 1980 to March 1984 (serving two terms in this period)

Historical Significance and National Pride

James Ronald Webster Day was officially established as a public holiday by the Government of Anguilla in 2010. This move was intended to ensure that Webster’s contributions would never be forgotten by future generations. Before his passing in 2016 at the age of 90, Webster was able to see the immense fruit of his labor—an island that had become one of the premier luxury travel destinations in the world, with a high standard of living and a robust sense of national pride.

The holiday matters because it serves as an educational tool. It provides a specific time for schools to teach the history of the 1967 Revolution. Without Webster's intervention, Anguilla might have remained a neglected backwater or been forced into a political union that did not serve its interests. The day celebrates the transition from "the land that time forgot" to a proud, self-governing people.

How James Ronald Webster Day is Celebrated

The atmosphere in Anguilla on March 2nd is one of respectful celebration. It is a day that balances formal state events with community-based joy.

The Official Parade and Ceremony

Speeches are delivered that recount the milestones of Webster’s life. Often, contemporaries of Mr. Webster—the "Foot Soldiers" of the Revolution—are invited as guests of honor, wearing their medals and ribbons with pride. National songs are sung with great fervor, particularly "God Bless Anguilla," which became a symbol of the island's struggle for identity.

Community Gatherings and Food

The beaches, such as Shoal Bay East, Maundays Bay, and Meads Bay, become hubs of activity. While some businesses are closed, the spirit of hospitality remains, and locals take the time to relax and enjoy the natural beauty of the island that Webster fought so hard to protect.

Boat Racing: The National Sport

Traditions and Symbols

Several symbols are prominently displayed on this day:

1. The Three Dolphins Flag: While the current Union Jack-based flag is the official one, the "Three Dolphins" flag of the 1967 Republic is often flown on this day. It represents the period of the revolution and the strength of the three islands (Anguilla, Sombrero, and the then-hoped-for inclusion of others) in unity.
2. Orange and White: Many people wear the colors associated with the revolution—orange for vitality and the sun, and white for peace and purity.
3. Wreath Laying: A solemn wreath-laying ceremony usually takes place at Mr. Webster’s gravesite or at his statue. This is a moment of silence and prayer, acknowledging the spiritual foundation that Webster himself leaned on during the difficult years of leadership.

Practical Information for Residents and Visitors

If you are in Anguilla on March 2, 2026, it is important to understand the local flow of the day.

Public Holiday Status