Anguilla Calendar of Events

Anguilla Events, Music & Nightlife

On Island Festivals and Events 2019

Feb 23Anguilla 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 4James Ronald Webster Day
National Holiday
March 2St. 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 24Moonsplash 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 19Good Friday
April 20Festival 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 21Elliot Webster Boat Race
Class A - Sandy Ground to Island Harbour
April 22Easter 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 10 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 16 to 18Anguilla Annual Lit Fest
May 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 10Whit MondayClass A Boat Races – Sandy Ground
June 16West Fest
Class A Race Meads Bay
June 17Celebration 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 10Welches Fest
June 17A Village Ting
Festival held at one of the islands heritage sites, the Old East End School, celebrating, good sports and art
June 23 to 25Cuisinart Golf Resort & Spa Anguilla Open Golf Tournament
July 14SXM Marigot Fete
Class B Marigot
July 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 21SXM Grand case Fete
Class B Grand Case
July 27Opening of Anguilla Summer Festival 19
Runs through August 11. Colorful expressions of Anguillan culture through dance, song, parades and boat racing
July 29Peter PerkinsClass A Sandy Ground
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 3South Valley Street Festival
Soca Band Class/Bandorama
August 4August Sunday - Heneiken Boat Race Warm Up (A&B Class) / Scotiabank Talented Teen Pageant
August 5August 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 6August Tuesday Boatrace / Junior & Senior Calypso Monary Competition
A Class race from Sandy Ground to Island Harbour
August 7August Wednesday Boatrace / Miss Anguilla Queen Pageant
Class A Sandy Ground to Blowing Point
August 8August 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 9Grand 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 10Anguilla Poker Run /Leeward Island Calypso Competition
August 11Champion of Champions Boatrace
A & B Class races at Sandy Ground.
November 25Anguilla'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 19Festival De Noel
Tree Lighting
December 19Heroes and Heroines Day
December 25Christmas Day
Public Holiday
December 26Boxing Day
Public Holiday