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Anguilla Summer Festival


Welcome to our guide for Anguilla Carnival.

Click the play button for our video guide to Carnival!

The summery month of August usually marks the end of the tourist season in Anguilla. By the end of July, the country slowly quiets down to a low hum. Hotels and restaurants start to close. This is when many businesses get ready to take their annual vacation.

This time also marks the start of Anguilla's biggest holiday festival... the Anguilla Summer Festival.

The Anguilla Summer Festival is Our Favorite Holiday Season!
Anguilla Summer Festival Carnival

Carnival, as it is still commonly called is celebrated across the Caribbean. It has its roots in emancipation, and most Caribbean countries celebrate theirs during the wintery months from November-March.

From the end of July until the middle of August, Anguilla is a buzz, with fervent excitement, beautifully colored costume parades and a sheer festive force that many look forward to with great anticipation.

Sandy Ground on August Monday, The Peak of Anguilla Carnival
Anguilla Sandy Ground

There's always something happening during Carnival. That's why we've created this page! So you can know what to expect and when...

So get your highlighter ready to pick your can't-miss Carnival events!

Summer Festival Run Down

The first Monday in August is key to the Anguilla Summer Festival and the Carnival Season in General.

It's official name is "August Monday." It marks the "true" beginning of Carnival and hosts two of the most popular events of the festival season... J'Ouvert and the August Monday Beach Party!

Before "August Monday", Carnival events happen both during the day and at night, usually at the Landsome Bowl Cultural Center in The Valley, the island's capital.

There are a number of pageantries, community festivals, soca and calypso competitions and a couple of small boat racing events. Events may vary from year to year, with some leaving and new ones popping up from time to time.

The Carnival schedule looks something like this :

Carnival Event Line Up For 2023
Anguilla Carnival Line up

After July, the big festivities begin! August Monday marks the start of the biggest days of Carnival. We'll get back to this later but for now let's break down each event.

Let's start in July...

  • July 16th - Miss Tiny Tott Pageant
  • July 22nd - Home Grown Street Poker // Food Festival
  • July 23rd - Miss Anguilla Swimsuit Competition
  • July 29th - Prince & Princess Competition
  • July 30th - Peter Perkings A Class Boat Race // Talented Teen Competition
  • August 3rd - Carnival Kick Off Light The Night Street Parade // Junior Calypso Competition

The Valley is the place to be in July for a variety of pageants and competitions that showcase the island's young talent. The Miss Tiny Tott and Prince & Princess pageant, the Talented Teen pageant, and the junior Calypso and Soca Monarch competitions are all held in the Valley, and they draw families from all over the island.

The Miss Tiny Tott and Prince & Princess pageant showcases the island's youngest talent through representatives of the primary and kindergarten schools. The Talented Teen pageant is a precursor for many contestants that further go on to compete in the Miss Anguilla pageant. And the junior Calypso and Soca Monarch competitions showcase the wit and creativity of young writers.

These pageants and competitions are a great way to celebrate the island's young talent and welcome the summer festive season.

Opening Night Kicks Off with a Fantastic Fireworks Display
Anguilla Carnival Kick Off

On opening night, usually the Friday before August Monday, The Valley streets come alive in a spectacular parade of dancing lights that ends with an explosive ;-) fireworks show. A perfect way to kick-off the official Summer Festival Week!

After The Carnival kick off...?

South Valley Street Festival and "Bands' Clash"

The South Valley Street Fair
The South Valley Street Fair

The weekend before August Monday is pretty lively. On Saturday, in the welcoming village of South Valley, cooks, artists and local craftspeople line the village streets with pop-up vendor and food stalls that use local resources to highlight the rich and local history of Anguilla.

Boothes With Beautifully Crafted Trinkets Line the Streets
 Anguilla Village Street Fair

For much of the day, the streets are filled with families and tourists alike. Perusing through the dazzling trinkets on display and enjoying the local musical contributions on stage as they croon the day away.

The Reigning Prince and Princess also make an Appearance!
 Anguilla Village Street Fair

Local favourites like the String Band gather a crowd and its not uncommon to lose 30 minutes of window-shopping dancing to their sweet, tangy tunes.

In the evening, just around the corner again at the Landsome Bowl, is the revered and deeply competitive "Band's Clash". Where local soca bands battle it out to see who can win the hearts (and the ears) of the locals.

Heineken A Class and B Class Boat Races

UFO, an A Class Racer and a Local Favourite!
Anguilla Carnival Boatrace

The next Sunday sees the island gathering over at Sandy Ground for one of the best A&B Class Boat Races on the Island. The Class represents the boat size and with both classes racing on the same day, that means double the races and double the fun! Boat racing enthusiasts flock to Sandy Ground in a pre-celebration of sorts for the Summer Festival Week ahead. Most maritime visitors set up camp here as well, in beautiful vessels that line the shores. Everyone's come to party and the fun is just beginning.

Soca Monarch Competition

The "Senior" Soca Monarch Competition usually occurs around this time. Talented musicians and lyricists take to the Landsome Bowl stage for a night of witty, sometimes raunchy but always funny entertainment. As the country's de facto "national genre" the competition for the Soca Monarch gathers quite a crowd. Revelry is always on the itinerary on this night.

Carnival Events in August

Now let's talk about August, where the most popular events take place...

  • Aug 7th - J'Ouvert // August Monday Boat Race & Beach Party
  • Aug 8th - A Class Boat Race // Miss Anguilla
  • Aug 9th - A Class Boat Race // Senior Calypso Competition
  • Aug 10th - Eyes Wide Shut // A & B Class Boat Races
  • Aug 11th - Grande Parade of Troupes
  • Aug 12th - Poker Run // Calypso Competition
  • Aug 13th - Champion of Champion A & B Class Boat Race

August Monday and Carnival Week

The first August Monday celebration was in 1940, and began as a boatrace celebration. On lookers gathered on the shores and to pass the time had food and drinks and a bit of a party. Today, it has evolved into one of the biggest beach parties in all of the Caribbean.

It all starts in the wee hours of the Monday morning...

August Monday J'Ouvert

A Sea of Partiers Make Their Way Down Sandy Ground's Hill
 Anguilla Jouvert Sandy Ground

"You can't have Carnival without J'Ourvert!" As goes the tradition in most Caribbean countries and in Anguilla it's no different. From 4-5am, revelers gather in the streets of The Valley armed with water and their favorite cocktail. Then, everyone makes their way to Sandy Ground's Road Bay... on foot!

Lively Crowds Surround Their Favorite J'Ouvert Music Truck  Carnival Jouvert Parade

That's right... what starts as a trickling crowd of sleepy feters, quickly turns into thousands of people coming out in droves. By 10am, the streets are filled with glitter, chalk and thousands of hands bouncing and jumping in unison behind their favorite music trucks.

Thousands Make Their Way To Sandy Ground
 Carnival Jouvert Parade

It's a good ol' time with never a frown in sight!

As the crowd of thousands (sometimes more than 5000) make their way to Sandy Ground, in just a couple of hours the second event for the day is soon to begin.

August Monday Boat Race & Beach Party

Party Boats Line Sandy Ground's Shores
It's beginning to look a lot like Carnival!
 Anguilla August Monday Sandy Ground

For the rest of the day, all festival roads lead to Sandy Ground as everyone prepares for August Monday boat races and the super fun August Monday Beach Party!

Both Boat Classes (A & B) set out to race around the island in the traditional Anguilla-style sail boats. For hours the beach is filled with spectators enjoying the music, local food and good vibes that abound as they wait for the winners to make their way back to Sandy Ground.

The beach gets packed... fast! Spectators and revelers come from all over the world to enjoy the day's beachy festivities.

August Monday ca. 2015
Anguilla Carnival Beach Party

Party Boats begin to line Sandy Ground's shores early in the afternoon.

On the Grand Stage, local and international music acts keep everyone up and dancing away for hours, sometimes well into the early hours of the morning.

August Monday marks the beginning of The Anguilla Summer Festival. And to many, that is just the beginning of what is a week of party, party, party!

August Tuesday - Class A Boat Race & Miss Anguilla Pageant

Boat racing enthusiasts and revelers gather back at Sandy Ground again on Tuesday for another lap of A Class boatraces. The A Class, bigger, boats begin the race in Sandy Ground around 2pm and this time end in Island Harbour. A shorter route, but fun nonetheless.

The evening follows with The Miss Anguilla Queen Pageant, one of the most anticipated shows during the Carnival week. Here contestants battle for the Miss Anguilla crown.

Miss Anguilla 2016, Carencia Rouse
Anguilla  Queen Show

Contestants perform on stage in a range of different categories, from Best Speech to Best Talent, to Best Evening Wear. All of which are feverishly celebrated by their respective supporters in the crowd. The night's usually filled with light hearted tension as the contestants compete for the crown.

August Wednesday - Class A Boat Race and Calypso Monarch Competition

Zooming To The Horizon
 Anguilla Boat Racing

Starting around 2pm, the boats set sail from Sandy Ground to Blowing Point and back.

Then in the evening Calypsonians croone for the title of Senior Calpyso Monarch. Calypso is rooted in the time of slavery when it was primarily a form of communication. Over the years it has become a form of creative and exuberant expression.

Calypso music may cover a variety of topics from social and political commentary to funny analogies with a cautionary tale woven into musical chords. This genre will always be a part of Anguillian culture and our regional Carnival culture.

August Thursday - Meads Bay A & B Class Boat Races and Eyes Wide Shut

Eyes Wide Shut started as a small event for only the most serious of partiers almost a decade ago. Now it's one of the most talked-about music festivals in the Caribbean, attracting thousands of people. With bigger and bigger headliners every year. It's the top day-break music festival in the Caribbean, hands down! The party begins at 1am and lasts until 11am the following morning.

Beautiful August Thursday Boat Races
Anguilla  Boatrace

And if dancing for almost 12 hours straight can't get you in the Carnival spirit, after the party, revelers head to Meads Bay for boat races and, you guessed it, another beach party . The races begin at 1:30pm. While spectators wait, they enjoy live music performances and locally sold food and drinks along Meads Bay.

August Friday - Grand Parade of Troupes

Carnival's Climax: The Grand Parade of Troupes Anguilla Carnival

August Friday is awaited by many. It is the second and final "Road March of Carnival!"

This Carnival attraction is all about vibrant, flamboyant colors and visually striking costumes. Different troupes dance and celebrate through the island's capital, interacting with the crowds and performing on-the-fly choreography. It is a great family event.

Grande Parade Of Troupes
Anguilla carnival

The streets are alive with dancing, and local soca music can be heard for miles. Anyone is welcome to watch, or even join in the parade.

The troupes are formed from different villages. They're also judged by a panel from the Carnival Committee, as this is a competition.

Colorful Costumes
Anguilla carnival

The beautiful, highly detailed costumes are judged on color, and the troupes on their performance.

Kids Love The Parade!
Anguilla Carnival parade

It is the most colorful day of Carnival. Imagine Anguilla, also known as "Rainbow City," getting even more colorful!

August Saturday - Anguilla Poker Run and Leewards Island Calypso Competition

Another highly talked about event is the annual Poker Run.

Poker Run Party Boats Preparing For The Day
Anguilla Carnival Poker Run

Boats from around the Caribbean enter for the chance to win a GRAND cash prize of $8,000. Stopping at multiple beaches around Anguilla, people party, eat, drink and play poker.

Poker Runners Compete in a Series of Challenges at Every Stop
Anguilla Beaches Poker Run

Come night fall, the Leeward Island Calypso Competition takes place at the Landsome Bowl. Calypso is ingrained into Anguillian culture, so this final competition is not to be missed.

August Sunday - Champion of Champions Boat Race

The very last day of Carnival brings together avid boat racing lovers. Sunday the 11th is the Champion of Champions boatrace. This is where the winner from each race during Carnival week competes against each other to see who really is the Champion of Champions.

Boats Get Ready for The Champion of Champions A Class Race
 Anguilla Boat Racing

Sandy Ground is always packed for this Sunday sailing afternoon. The atmosphere is a lot less chaotic than at the beginning of the Carnival week on August Monday. But the crowds are as supportive as ever. It is a great way to close the Carnival season and soak up the island's unique culture all at the same time.

After Carnival, Anguilla returns to its quiet, serene self. But the memories of the festivities linger long after the last costume has been packed away. Until next year's Carnival, Anguillans will look forward to the next time they can come together to celebrate their island's culture and heritage.

This has been an in-depth look at the Anguilla Summer Festival. But it doesn't compare to experiencing it for yourself. So come to Anguilla next year and join in the festivities!

See you there!