7 Things to Do in Jamaica’s Cockpit Country

The Cockpit Country is Jamaica’s last true wilderness. With its dramatic limestone hills, thick impenetrable rainforests, numerous caves, sinkholes and vibrant Maroon villages, the Cockpit Country offers a rich mix of nature, history and culture. It’s also Jamaica’s largest mountain range at three times the size of the Blue & John Crow Mountains, measuring 780km2 and spanning five parishes. That being said, the Cockpit Country receives significantly fewer visitors because its karst landscape, high humidity, dense vegetation and limited surface groundwater make it an inhospitable and unforgiving destination. However, those who make the trek are in for a treat as the Cockpit Country is very beautiful and home to a large portion of Jamaica’s biodiversity. For travelers seeking an off-the-beaten-path adventure, here are seven unforgettable things to do in the Cockpit Country.

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How to Celebrate Reggae Month in Kingston, Jamaica

Every February, Jamaica comes alive with rhythm, history and pure cultural energy as we celebrate Reggae Month. This isn’t just about music — it’s about honoring the legends, the communities, and the global movement that reggae created. If you’ve ever wanted to experience Jamaica beyond the beaches, this is the best time to visit. From Kingston’s musical landmarks to immersive cultural tours, Reggae Month offers travelers a deeper, richer connection to the island. Here’s exactly how to plan the perfect Reggae Month trip — including the best tours, where to stay in Kingston and how to get around.

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A Dreamy Day at the Strawberry Hill Resort

The Jamaican Blue Mountains are my favourite place on Earth– a tranquil highland escape of cool rolling mist, lush greenery, breathtaking views and rich history. Perched high in Jamaica’s Blue Mountains lies the Strawberry Hill Resort— the sort of escape that feels a world away from the bustling city of Kingston, although it’s only 20km away from the city centre. Strawberry Hill is a cozy boutique hotel consisting of white-washed cottages clustered across 26 acres. This mountainside retreat is part of Island Outpost, a collection of luxury Jamaican hotels and villas owned by Chris Blackwell, the former record producer behind Bob Marley’s breakout success. With that said, here’s how my recent day trip to the Strawberry Hill Resort went, and what to expect.

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Nonsuch Falls: Jamaica’s Tallest Waterfall

Tucked away in the quaint rural community of Nonsuch, Portland, lies the tallest waterfall in Jamaica. At 291 feet (89m) from its base, Nonsuch Falls is actually 100 feet taller than Niagara Falls, North America’s most visited waterfall! I’ve delayed my visit to Nonsuch Falls a few times to ensure I’d capture it at peak water volume which only happens just after heavy rains. My wait was rewarded with a memorable adventure earlier this month which far exceeded expectations. With that said, here’s everything you need to know to plan a visit to Nonsuch Falls.

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Craighton Estate: A Blue Mountain Coffee Tour Near Kingston

Nestled in the rolling hills overlooking Kingston and St. Andrew, Jamaica, lies the Craighton Estate in Irish Town. Craighton Estate is a perfect half day-trip from Kingston for travelers who want history, scenery, coffee and a little mystery rolled into one visit. Whether you’re a coffee lover or simply someone who loves wandering through old great houses and plantation grounds, Craighton delivers a peaceful, authentic Jamaican experience without the crowds. Here’s how to reserve this bean-to-cup coffee tour and what to expect.

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Treasure Beach, Jamaica Reopens with Strength & Heart

After weathering the passage of Hurricane Melissa, I’m proud to announce that Jamaica is open once more! Treasure Beach has always held a special place in my heart because it represents the quieter, authentic side of Jamaica where community, resilience and simplicity shines bright. I love its laid-back energy, the warmth of the people, the sense of safety, and the way life there feels unhurried and deeply connected to the land and sea. Seeing Treasure Beach reopen to tourism after Hurricane Melissa fills me with genuine happiness and pride, because this South Coast community has weathered hardship with resilience and grace. With that said, I’ve teamed up with these Treasure Beach locals to share where’s open and why their community ought to be on your travel radar.

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Cockpit Country: Historic Hike from Troy to Windsor

When most people think of Jamaica, they picture white sand beaches but 50% of the island is rugged and mountainous. Jamaica’s largest mountain range is the Cockpit Country which is three times the size of the Blue & John Crow Mountains, spanning 780km2 and five parishes. Cockpit Country got its name from its unusual karst landscape, where steep-sided limestone hills and deep valleys create a terrain that looks like the cockpits of old ships, or an upturned egg carton if you will. Before this hike, the closest I’d come to visiting the Cockpit Country was to Accompong, a Maroon village located on its outskirts. Why? The Cockpit Country is one of the most inhospitable places in the world. However, when an invitation came to hike the forgotten Troy to Windsor trail which traverses the Cockpit Country, I accepted. Here’s how this adventure went.

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Catherine’s Peak: St. Andrew’s Highest Point

Catherine’s Peak, located in the Jamaican Blue Mountains, is the highest point in the parish of St. Andrew. This peak is named after Catherine Long, the wife of Sir Henry Moore who served as the Governor of Jamaica in the mid-1700s, as she is believed to be the first white woman to climb the 5,050-foot-high peak in 1760. Catherine’s Peak is an easy trail– perfect for beginner hikers, and starts at Newcastle, the JDF military base nestled in the Blue Mountains. Here’s everything you need to know about hiking to Catherine’s Peak.

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Live the Sweet Life at Pure Chocolate Jamaica

Did you know that Jamaica produces some of the world’s best chocolate? According to the International Cocoa Organization, Jamaica is one of only eight countries globally to exclusively produce fine flavour cocoa beans which makes the best chocolate. For centuries, Jamaica mainly exported its cocoa beans and very little chocolate was produced here. However, there are now half-a-dozen local chocolatiers and Jamaican chocolate brands changing the game, one of which is the award-winning Pure Chocolate Jamaica brand in Island Village Mall, Ocho Rios. Every weekend, this chocolate factory opens its doors to chocolate lovers from across the globe, allowing them to participate in a two-hour interactive workshop. I finally made it to Pure Chocolate Jamaica’s workshop last month, so here’s my recap of the tour and how to plan a visit.

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A Visit to the Old Pera Windmill & Beach

Old Pera, a small village in St. Thomas, Jamaica’s easternmost parish, is home to a historic windmill and beach by the same name. Built around 1780, this windmill is a remnant of the sugar estates which once dotted Jamaica. The Pera Estate dates back to 1682 and was originally owned by Sir Thomas Lynch, an English lawyer who had three stints as Governor of Jamaica before his death in 1684. The estate was eventually subdivided into two: New Pera and Old Pera, both of which are sleepy rural villages today. Here’s what’s left of them.

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