|Feb 25||Anguilla Beautification Club Annual Flower & Garden Show
Celebrate the beauty of Anguilla and enjoy fresh flower arrangements, indigenous plant arrangements, creative arrangements including driftwood, flowering and foliage plants in containers, miniature arrangements, miniature gardens, hanging baskets, a display of orchids, needlework with oral decor, and the school art display
|March 2||James Ronald Webster Day
|March 4||St. Gerard's Garden Party
At the Roman Catholic Church grounds
St. Gerard’s Garden Party has become a standard celebration for all of Anguilla to enjoy. The festival features a traditional West Caribbean dinner, entertainment and dancing
|March 21 to 24||Moonsplash Annual Music Festival
Occurs on the weekend of the full moon in March. The festival showcases Caribbean and international talent at the Dune Preserve, Rendezvous Bay Beach
|April 19||Good Friday|
|April 20 to 21||Festival Del Mar
On picturesque Island Harbour, a celebration of the sea, the festival includes deep sea fishing contests, boat races, triathlons, culinary competitions, string band music, and a range of other activities.
|April 23||Easter Monday Boat Racing
At Sandy Ground- fun day, rallies, sports meets, family gatherings & picnics
|May 1||Labour Day 10:00 am until
Public Holiday. Fun Sports Day amongst Government Departments and Private sector companies. James Ronald Webster Park
|May 12 to 15||Anguilla Annual Yacht Regatta
Hosted by the Anguilla Sailing Association (ASA) and the Anguilla Tourist Board, the Annual Anguilla Yacht Regatta attracts sailors from across the Caribbean and around the world. A number of races will be held, and the event culminates with a post- race reception
|May 30||Anguilla Day Celebrations
The most significant holiday on the Anguillian calendar of events, and culmination of the month long celebrations to commemorate Anguilla Day and the round the Island boat race.
|June 10||Whit Monday|
|June 17||Celebration of the Birthday of Her Majesty the Queen
Public Holiday. All uniformed organizations parade at James Ronald Webster Park in the morning and cocktails are served in the evening at Government House to invited guests. A Class Boatrace at Crocus Bay
|June 23 to 25||Cuisinart Golf Resort & Spa Anguilla Open Golf Tournament|
|July 14||Annual Miss “Tiny Tot” Pageant
Part of the Pre Summer Festival events.
This pageant takes place at LBCC for girls ranging from 8 – 9 years old. Fun evening for children with Cartoon Characters.
|July 16||John T. Memorial Cycling Race
Anguilian cyclists compete with others from throughout the Caribbean on a challenging course that winds its way across our island. The route begins in The Valley before going east to Sandy Hill roundabout, it continues to the West End, then on the way back, loops through Sandy Ground before returning to the east and climax at The Valley. Male cyclists perform three laps and female participants complete two laps. Day one sets the stage as a time trial and heightens with the race on day two!
|July 27||Wet Fet 7|
3 to 13
|Anguilla Summer Festival
Anguilla comes alive with 11 days of fun, food and boat racing. The Anguilla Summer Festival features musical performances, cultural and kids parades and a number of pageants and competitions and boat
racing. The Anguilla Summer Festival features musical performances, cultural and kids parades and a number of pageants and competitions.
|August 3||South Valley Street Festival
Soca Band Class/Bandorama
|August 4||Absolut Boat Race Warm Up (A&B Class) / Scotiabank Talented Teen Pageant|
|August 5||August Monday J’ouvert Morning, Emancipation Day
Caribbean Beach Party (Sandy Ground) 4:30am -2:00am / Heineken Boat Races
Public Holiday. At the crack of dawn people from all over the island dance in the streets from the valley to Sandy Ground until noon. Taking to the streets in the Valley at 4:30 am and reveling to Sandy Ground accompanied by the leading local bands.
Then it’s the A & B Class Heineken Boatraces and the hottest Caribbean Beach Party.
|August 6||August Tuesday Boatrace / Junior & Senior Calypso Monary Competition
A Class race from Sandy Ground to Island Harbour
|August 7||August Wednesday Boatrace / Miss Anguilla Queen Pageant
|August 8||August Thursday Boatrace / Eyes Wide Shut
Public Holiday. A day for picnics and family reunions and the ATB-sponsored A & B Class Boatraces at Meads Bay, with Live Entertainment (2:00pm - ?). Handmade racing boats compete everyday of carnival for the grand prize. Great party also!
|August 9||Grand Parade of Troupes (Constitution Day) 1:00 pm -9:00pm
Public Holiday. 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.
|August 10||Anguilla Poker Run /Leeward Island Calypso Competition|
|August 11||Champion of Champions Boatrace
A & B Class races at Sandy Ground.
|November 25||Anguilla's Optimist Race Against Aids
Held on the eve of International World AIDS day, this event includes a half-marathon, a 10k run and a 5k walk/run.. Public awareness campaign to raise funds for AIDS related services
|December 12 to 19||Festival De Noel
|December 19||Heroes and Heroines Day|
|December 25||Christmas Day
|December 26||Boxing Day