Mary's Takeout at Cudjoe Head for Breakfast on Montserrat

The Best Time to Visit Montserrat and The Legend of Cudjoe Head

What’s the best time of year to visit [insert Caribbean destination name here]…? As you might imagine, it’s a question we’re asked all-too-often. Answers vary greatly, of course, depending on the different types of things individual travelers like to do. As for the best time to visit Montserrat though, one particular time of year stands out. Especially if you love history, are culturally curious, and like to party. That time of year is mid-summer. The big occasion – Cudjoe Head Festival.

To truly appreciate the Cudjoe Head Festival, it helps to understand two things.

  1. Who was Cudjoe?
  2. What happened to his head?

You see, this vibrant and uniquely Montserratian celebration has roots in a most macabre chapter of Caribbean history…

The Tragic Legend of Cudjoe

Few names carry as lasting and esteemed a status in Montserrat as Cudjoe. The man was a slave who toiled in Montserrat during the 18th century. According to legend, he escaped his captors. Like scores of other Africans who risked their lives in order to win their freedom, though, Cudjoe was eventually captured.

Slave masters in Montserrat sought to make an example of the runaway slave, the better to keep the rest of the remaining Africans in bondage in line. Their solution: cut off his head and hang it in a conspicuous spot everyone would see. Their choice spot: the silk cotton tree pictured above.

SE view from Cudjoe Head, Montserrat
SE view from Cudjoe Head, Montserrat | SBPR

Then as now, the stalwart tree sits at a strategic bend of a primary road that snakes sharply up a steep hill. For those taking the path on foot, the tree would’ve no doubt made an ideal resting spot. Even today it still serves as a prime landmark. Hang anything from these limbs and no doubt everyone in Montserrat will see it.

Cudjoe Head, the Village

As you might imagine, the effect of Cudjoe’s murder and beheading left an indelible mark on the history of Montserrat. So much so, in fact, that the village that sprung up around the silk cotton tree eventually adopted his name.

The hilltop enclave of Cudjoe is more loose collection of edifices than what most people would consider a village. Like most of Montserrat, it’s extremely quiet and peaceful here. On our visit last September, Patrick and I stopped here regularly to enjoy breakfast and lunch treats at Mary’s Takeout.

Everything Fresh in Cudjoe Head, Montserrat
Everything Fresh is another good options for eats in Cudjoe Head, Montserrat | SBPR

The pretty and petite pink snack hut beneath one of the Caribbean’s most infamous silk cotton trees serves scrumptious fry bake and saltfish breakfast sandwiches. Mary’s chicken roti is also among the best on the island. Even if you don’t know or appreciate the history here, Mary’s delights are well worth a visit whenever you’re in Montserrat.

The Best Time to Visit Montserrat

At the end of July/beginning of August, sleepy Cudjoe comes alive with the sounds of steel pans, drums, road races, and general revelry. It’s all part of the annual Cudjoe Head Festival.

The celebration originally started in 1989 as a means of community-building, with an emphasis on the island’s African cultural heritage. The family-friendly event has encompassed a wide range of activities over the years. Cycling, running, and crab races; dance competitions; string bands; steel bands; iron bands; art exhibitions; and more.

All of it plays out in the street in and around this venerable intersection of history where the people of Montserrat annually turn a legendary tragedy into a triumph for all to share in.



Last updated by Steve Bennett on .

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