|February 22||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
|February 22||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 2||James Ronald Webster Day
National HolidayThe Father of the Nation, James Ronald Webster, was awarded a public holiday on his birthday for his role in leading Anguilla's separation from the Federation of St. Kitts-Nevis.
|March 13 to 15||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
|March 18 to 23||5 Nights Anguilla 2020
|April 1 to 30||Extraordinary Eats
A vibrant month-long celebration of Anguilla's rich food culture and culinary arts. Including the "Taste of the Strip" food market, mixology, and cookery classes, talks at the Agricultural Farm, and food experiences, such as mango or salt picking, a
"Bake-Off" competition, Chef's Table menu tastings for both the public and private sectors hosted by the Anguilla Tourism Board, and special three-course "prix-fixe" menus. The festival will conclude with a "grand finale" dinner prepared by a selection of international chef talent
|April 10||Good Friday|
|April 11||Sax & Reggae Sunday at Sunshine Shack
Sunshine Shack, Rendezvous Bay
|April 11 to 12||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 13||Easter Monday Boat Racing
At Sandy Ground- fun day, rallies, sports meets, family gatherings & picnics. Class A Sandy Ground to Sandy Hill & Back
|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 7 to 12||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 14 to 17||Anguilla Annual Lit Fest A celebration of "books and beaches", the festival honours Anguilla's literary heritage and ongoing presence through a packed schedule of talks, workshops and presentations, as well as spoken word, hip hop and open mic sessions. The lineup includes New York Times bestselling authors, fresh writing talent, poets, publishers, historians, and lecturers as well as the "Pride of Anguilla" home-grown authors and poets.
|May 21 to 26||Pre-Anguilla Day Race/ Fashion Expo
Class A Sandy Ground
|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 1||Whit Monday/Welches Fest|
|June 15||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 TBA||Queen's Birthday Boat Race
Class A Race Crocus BayThe annual Queen's Birthday Boat Race commemorates the birthday of Queen Elizabeth II. It is the only boat race held on Crocus Bay for the Season.
|June 12 to 17||A Village Ting
Festival held at one of the islands heritage sites, the Old East End School, celebrating, good sports and art
|June 13 to 14||West Fest
|June TBA||Cuisinart Golf Resort & Spa Anguilla Open Golf Tournament|
|July TBA||SXM Marigot Fete
Class B Marigot
|June 21||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 TBA||SXM Grand case Fete
Class B Grand Case
|July TBA||Opening of Anguilla Summer Festival 19
Runs through August 11. Colorful expressions of Anguillan culture through dance, song, parades and boat racing
|July TBA||Peter PerkinsClass A Sandy Ground|
2 to 9
|Anguilla Summer Festival
Anguilla comes alive with 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||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 4||August Tuesday Boatrace / Junior & Senior Calypso Monary Competition
A Class race from Sandy Ground to Island Harbour
|August 5||August Wednesday Boatrace / Miss Anguilla Queen Pageant
Class A Sandy Ground to Blowing Point
|August 5 to 6||August Thursday Boatrace / Eyes Wide Shut
Public Holiday. A day for picnics and family reunions and the ATB-sponsored A & B Class Boat Races at Sandy Ground, with Live Entertainment (2:00pm - ?). Handmade racing boats compete everyday of carnival for the grand prize. Great party also!
|August 7||Constitution Day/Grand Parade of Troupes
1:00 pm -9:00pm - The Valley
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 8||Anguilla Poker Run /Leeward Island Calypso Competition|
|August 9||Champion of Champions Boatrace
A & B Class races at Sandy Ground.
|August TBA||South Valley Street Festival
Soca Band Class/Bandorama
|August TBA||August Sunday - Heneiken Boat Race Warm Up (A&B Class) / Scotiabank Talented Teen Pageant|
|December 12 to TBA||Festival De Noel
|December 25||Christmas Day
|December 26||Boxing Day
|December TBA||Heroes and Heroines Day|