St Patrick’s Festival is Montserrat's largest festival dedicated to St. Patrick's Day. Montserrat is one of only a few countries outside of Ireland that observes March 17 as a national holiday. The lively celebrations marking Ireland's national holiday last an entire week in Montserrat.

On the "other emerald isle," St. Patrick's Day commemorates the March 17, 1768 slave uprising in Montserrat. The day is marked by plenty of drinking, partying, and a lively parade, as it is in Ireland. Montserrat's St. Patrick's Day Festival, on the other hand, includes masked street dancers known as Masqueraders, a recreated slave village complete with a slave feast of local food, and a junior calypso competition. There is also a Freedom Run between Cudjoe Head and Salem Park, as well as kite flying, top-spinning, and unique music with African and Irish influences.

Takes place: on March 17 and lasts one week.

The next one in the list of the most famous festivals in Montserrat that Toplist would like to introduce to you is Calabash Festival. The first Montserrat Calabash Festival was planned in 2005. Florence Griffith Joseph, a local businesswoman, came up with the idea, which was brought to life with the help of volunteers from Montserrat's hospitality sector. As a result, the Montserrat Calabash Festival held its first celebration in July 2006. The main sponsors are the Montserrat Government, the Montserrat Tourist Board, The Royal Bank of Canada, The Bank of Montserrat, and several local Montserrat businesses.

This mid-July festival honors Montserrat's most useful fruit, which is used to make many of the island's traditional musical instruments, eating implements, and other items. This seven-day event includes a cricket match, gospel concert, island boat tour, and Irish lecture series, as well as a nail and hair show followed by a jazz concert.

Takes place: in mid-July

To continue, Toplist will present about Cudjoe Head Celebrations as one of the most famous festivals in Montserrat. During the Cudjoe Head celebrations, which take place the first weekend of August, Montserrat celebrates its African ancestry. Cudjoe Head was named in the 18th century after a slave named Cudjoe who ran away from his master.

He was apprehended and lynched at Cudjoe Head Corner, and his head was placed on a silk-cotton tree to remind anyone thinking of fleeing what the punishment would be if they were apprehended. The celebrations have expanded to include a steel band performance, a road race, and an exhibition of goods made in the village. Furthermore, Cudjoe Head Eve, the night before the festival, is now known for revelry and fun, with a street festival featuring live music and vendors. This two-day August festival features a string band and masquerades, as well as bike and relay races.

Takes place: the first weekend of August

In mid-November, Montserrat's largest literary festival takes place over three days. Bird watching, hiking, and Soufrière Hills Volcano viewing parties, as well as fascinating literary workshops, readings, lectures, and panel discussions, attract authors and bibliophiles. Thanks to those exciting activities, the Alliouagana Festival of the Word is among the most famous festivals in Montserrat.

Alliouagana Festival of the Word has attracted international authors such as Jason Reynolds, Eric Jerome Dickey, Frané Lessac, Marie Elena John, Olive Senior, and Earl Lovelace since its inception on November 13 – 15, 2009. Renowned lecturers and speakers on Caribbean identity, nationalism, and creativity have included the late Dr. George A. Irish, Sir Hilary Beckles, Sir Howard Fergus, Dr. Carolyn Cooper, Dr. Yvonne Weekes, and Opal Palmer Adisa. Thanks to that, the Alliouagana Festival of the Word has become one of the most famous festivals in Montserrat. Every year, the Alphonsus "Arrow" Cassell Memorial Lecture Series precedes the three-day literary festival.

Takes place: in mid-November and lasts 3 days

From mid-December to the New Year, Montserrat's take on traditional Caribbean festivities is available. It's a homecoming for several former residents who fled the island after the Soufrière Hills Volcano erupted, who have returned to enjoy Christmas and Carnival. The annual Montserrat Carnival is a multi-day event that celebrates the island's music, pageantry, heritage, and culture. It is one of the Caribbean's most anticipated end-of-year carnivals, attracting thousands of visitors during the Christmas season.

During the year-end festival, Montserrat erupts with an explosion of color, music, revelry, and creativity from mid-December to New Year's Day. Visitors to Montserrat gain a true understanding of the island's culture and the excitement and revelry that Montserratians express at this time of year. Cultural activities for visitors and residents include calypso competitions, masquerade street performances, the festival Queen Competition, and a parade of costumed troupes on New Year's Day. There are J'ouverts where everyone can jump up behind a sound system, with locals sometimes spraying water and/or powder over the crowd in the spirit of revelry.

Takes place: from mid-December to the New Year's Day