Anguilla Calendar of Events

Anguilla Events, Music & Nightlife

On Island Festivals and Events 2020

February 22Anguilla 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 22St. 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 2James 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 15Moonsplash 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 235 Nights Anguilla 2020
Nathan's Cove
April 1 to 30Extraordinary 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 10Good Friday
April 11Sax & Reggae Sunday at Sunshine Shack
Sunshine Shack, Rendezvous Bay
April 11 to 12Festival 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 13Easter Monday Boat Racing
At Sandy Ground- fun day, rallies, sports meets, family gatherings & picnics. Class A Sandy Ground to Sandy Hill & Back
May 1Labour Day 10:00 am until
Public Holiday. Fun Sports Day amongst Government Departments and Private sector companies. James Ronald Webster Park
May 7 to 12Anguilla 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 17Anguilla 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 26Pre-Anguilla Day Race/ Fashion Expo
Class A Sandy Ground
May 30Anguilla 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 1Whit Monday/Welches Fest
June 15Celebration 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 TBAQueen'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 17A Village Ting
Festival held at one of the islands heritage sites, the Old East End School, celebrating, good sports and art
June 13 to 14West Fest
June TBACuisinart Golf Resort & Spa Anguilla Open Golf Tournament
July TBASXM Marigot Fete
Class B Marigot
June 21John 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 TBASXM Grand case Fete
Class B Grand Case
July TBAOpening of Anguilla Summer Festival 19
Runs through August 11. Colorful expressions of Anguillan culture through dance, song, parades and boat racing
July TBAPeter 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 3August 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 4August Tuesday Boatrace / Junior & Senior Calypso Monary Competition
A Class race from Sandy Ground to Island Harbour
August 5August Wednesday Boatrace / Miss Anguilla Queen Pageant
Class A Sandy Ground to Blowing Point
August 5 to 6August 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 7Constitution 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 8Anguilla Poker Run /Leeward Island Calypso Competition
August 9Champion of Champions Boatrace
A & B Class races at Sandy Ground.
August TBASouth Valley Street Festival
Soca Band Class/Bandorama
August TBAAugust Sunday - Heneiken Boat Race Warm Up (A&B Class) / Scotiabank Talented Teen Pageant
December 12 to TBAFestival De Noel
Tree Lighting
December 25Christmas Day
Public Holiday
December 26Boxing Day
Public Holiday
December TBAHeroes and Heroines Day