February TBA: Community Foundation Classical Concert
The Anguilla Community Foundation invites musician from all over the world to perform at the Bethel Methodist Church to raise funds for their charitable organization. (7:30 – 9:00)
February 25 & 26: Annual Flower and Garden Show
Two days of flower displays and competitions on the grounds of Historic Wallblake House. (11:00 am – 6:00 pm)
March 2: James Ronald Webster Day
Speeches and tributes made to the Father of the Nation James Ronald Webster takes place at Webster’s Park. (8:00 am – noon)
March 3: St. Gerard’s Garden Party
Hosted on the Grounds of historic Wallblake House, showcasing food from other islands prepared members of St. Gerard’s congregation with live music and dancing. (7:30 – until...)
March 8 - 11: 21st Annual Moonsplash Festival
Takes place at the Dune Preserve on Rendezvous Bay, normally around the first full moon before Easter. The concerts are hosted by Anguilla’s very own Bankie Banx, featuring international and regional artists from around the world. (8:00 pm – until)
April 7 & 8: Festival Del Mar, Easter Saturday & Sunday
Celebrating all things of the sea in the beautiful fishing Village of Island Harbour. Deep Sea fishing competition, swimming races, crab races and culinary competition, life string band music all part of the activities for this two day event. (10:00 am – 11:00 pm)
April 12 – 16: Ruben Brown Golf Tournament
A series of Golf tournaments played by international sports celebrities, the event takes place at the Temenos Golf Course. (Tee off is at various times)
April 9: Easter Monday Boatrace
A Class Egbert Connor Boatrace at Sandy Ground (2:00 pm)
May 3: National Day of Prayer
An entire day of prayer at the House of Assembly, in churches and other public places around the island.
May 7: Labour Day
Competitive games between the various on island social clubs on the Ronald Webster Par, also known as Fun Day. (10:00 am - until...)
May 4, 5, & 6: 9th Annual Anguilla Yacht Regatta
Yacht racing between the regional racing fraternity, with a local B class boat race normally on the last day of the regatta. (various starting times)
May 19: Miss Caribbean Talented Teen
A pageant for Teens within the region, the event is staged at the Landsome Bowl Cultural Centre (8:00 – until...)
May 28: Whit Monday Fest
Welches Fest takes place in the ball field in Welches Village. Starting around 5:30 am you can have an old fashioned breakfast of flour pap to start your day. All things at this fest are of yesteryear including food, toys and games and music. (5:30 – 8:00 pm)
May 26: Valley Street Festival
Local vendors, Farmers Association, Scouts and Guides and the Department of Youth & Culture in partnership with the Anguilla Tourist Board in bring this event to the area of the Peoples Market with Domino, face painting, live music games and a cycling competition for Primary school students. (10:00 am – 6:00 pm)
May 30: Anguilla Day Celebrations
The most significant holiday on the Anguillian calendar of events, throughout the entire month of May there are a number of activities leading up to AXA Day and the round the Island boatrace.
June 4: Diamond Jubilee
60th Anniversary of the reign of Queen Elizabeth II of England.
June 5: Celebration of the Birthday of Her Majesty the Queen
All uniformed organizations have a parade on the park and/or cocktails at government house.
June 8: Miss Venus Swimsuit Competition
Takes place at LBCC. Participants from Anguilla and the neighbouring islands compete in a three segment competition of one piece, bikini and original design suit. (8:00 pm – until...)
July 15: Annual Miss “Tiny Tott” Pageant
Part of the Pre Summer Festival events, this pageant takes place at LBCC for girls ranging from 7– 8 years old. (4:00 pm – until...)
July 14 & 15: John T. Memorial Cycling Race
Annual Race held over a two day period with participation from regional and international cyclists. (10:00 am – until...)
August 3 - August 12: Anguilla Summer Festival
Eleven days of boatrace, pageants, competitions and street activities. (various starting times at LBCC)
August 4: South Valley Street Fair
Members of the South Valley Community unite and produce a fair with local food, cooking competitions and music. (10:00 am – until...)
August 6: J’ouvert Morning, August Monday Emancipation Day
Taking to the streets in the Valley at 4:30 am and reveling to Sandy Ground accompanied by the local for the A & B Class Boatraces and the Caribbean Beach Party. (4:30 -11:00 am)
August 9: August Thursday
A day for picnics and family reunions and A & B class Boatraces at Maundays Bay. (2:00 pm)
August 10: Grand Parade of Troupes
Troupes from villages all over the island come together on the last Friday of Summer Festival to parade through the streets of the Valley. Colourful costumes depicting cultural and fantasy themes and the winner of Road March is announced. (1:00 pm -9:00 pm)
November 8 - 11: Tranquility Jazz Festival
The only of its kind in the Caribbean “Strait Ahead” jazz for the serious Jazz aficionados. (8:00 pm – midnight)
November 24 -30: Tourism Week
Includes cultural fair, church service, lectures at the various schools and concludes with the AHTA grand gala and awards banquet.
November 24: Anguilla’s Optimists Race against Aids
Public awareness campaign to raise funds for AIDS related services.
December 11: Christmas Tree Lighting
Lighting of trees in the Old Valley Well area, Carol serenading, string band competitions are some of the activities
December 13 – 19: Festival De Noel
Competitions and pageants held on the grounds of the Old East End school