Summer Festival on Anguilla, similar to other Caribbean emancipation activities, has been celebrated on the island for over a quarter of century. Its roots however, are found in decades-old, traditional August Monday fairs, bazaars and the old-time Christmas festivities.  These historical activities included many African-influenced cultural expressions of island life and were mainly organised by the churches. Traditional August Monday celebrations featured among other things, wire walkers, May Pole dancers, Mock-a-Jumbies and games.

One of the most significant days of the Anguilla Summer Festival is August Monday – the first Monday of August. This significance is closely associated to 1^st August, 1838, the day when enslaved Africans in British colonies were freed of chattel slavery after centuries of enslavement. Anguilla started its formal August Monday celebration in 1940, when activities began to include boat racing, the island’s national sport.  Since then, Boat Racing has been merged with other cultural aspects of carnival, and the celebrations have become what we now know as Anguilla Summer Festival.

The art of Boat Racing was born out of the Anguillians’ natural love for and dependence of the sea. This love was further cemented by the hardships of life on the island, and is symbolic of the struggle for survival, that Anguillians endured on the almost desert terrain.  The frequency of droughts forced an intimate dependence on the sea, to compliment and subsidise what the land could not offer. The failure of the plantation economy from the 1700’s, and the severe economic conditions forced Anguillian menfolk to seek employment overseas. This included traveling to the Dominican Republic to cut cane in the prosperous cane fields of Macoris and La Romana. It is through these experiences – the dependence on the sea and the voyages to the Dominican Republic – that the art of boat building and the skills of boat racing were born.

Incredibly, in the days when men from the Leeward Islands voyaged to the Dominican Republic to cut cane, many were ferried by Anguillian crafted and captained boats. Every trip to and from Santo Domingo soon became a fiercely contested race, as were fishing trips at home. Many of today’s racing boats are named in honor of late 19th century cargo sloops that ploughed the seas of the southern and western Caribbean. Each boat is a personality, a legend with a story, and has a faithful following.

During the Anguilla Summer Festival, Boat Racing is a daily celebration with the tranquil and pristine beaches becoming bustling venues of energy and excitement.  The clear water and unique crispy white sand are soaked and trampled upon by thousands of boat racing fans, enthusiasts, picnickers and dozens of visiting yachts and pleasure boats. There is live music and varying blends of food and drinks.

Today’s festivities still exude the same charm and spirit as in the early days. The Anguilla Summer Festival calendar of events now often includes J’ouvert, Miss Anguilla Pageant, Prince and Princess Pageant, Junior and Senior Calypso and Soca Monarch Competitions, Ms. Talented Teen Pageant, Grand Parade of Troupes, and the Leeward Islands Calypso Monarch Competition. All these activities take place at the Landsome Bowl Cultural Centre, the historical site of the Warden’s residence which was destroyed in the 1967 revolution.

The Anguilla Summer Festival Committee’s goal is to revive some of the traditional art forms and merge them with our modern expressions of mass playing and cultural extravaganzas.