The colonial ties, picturesque beaches and fantastic rainforests in Montserrat make it a hiker’s heaven. You’ll be able to see views of the ocean, take snapshots of the volcano and spot the tropical bird, reptile and bat species common in the sections of rainforest.

The island is also steeped in history, perfect for a guided hike around the old banana plantations, ruined villages and the sections of island currently still recovering from the 1995 volcano eruption.

The island is mountainous, so most hikes take you up dramatic peaks and into lush valleys full or greenery, or along to coast to spot marine life living amongst the coral close to shore. It’s also known as the friendliest place in the Caribbean, so you can feel completely safe hiking through the mountains, even if you choose not to take a guide.

Do I Need A Guide?

If you’re choosing not to take a guide along with you, that’s totally fine. The majority of trails to hike are already marked out with helpful signposts so you don’t get lost. Be sure to take the right clothing and footwear and plenty of food and water for the longer trails; refreshments can be a long way away.

So, which trails are the best?

1. Rendezvous Beach Trail

Rendezvous Beach is one of the most well-known starting points for hikers as it has trails across the hills looking right out into the ocean and down on the sandy white beach of the northernmost point of Montserrat.

The trail has greenery housing tropical birds and reptiles and the fresh vegetation, depending on the time of year, will yield colorful flowers and fruits. The trail is marked out and can be completed without a guide, however, it is a moderately difficult trail, so hiking footwear and plenty of water will be required.

2. Oriole Walkway

This hiking trail begins at the Hilltop Café and wanders through the rainforest into the areas most heavily populated by the oriole, the island’s national bird. You’ll find colorful rainforests, amazing scents and unmissable photo opportunities.

3. The Dry Waterfall

A few years ago, a storm exposed part of the cliffside, showing petroglyphs dating back 1500 years. The trail to view these is really worth the trip but is easily missed if you aren’t with a guide. The carvings are found deep within the rainforest and the trail takes you down a dried up river bed. It’s a fairly difficult trail for a beginner.

4. Blackwood Allen Nature Trail

This trail is surrounded by luscious fruit trees and takes you right up into the mountains. It’s a great way to experience the rich flora and fauna on the island and the pathway is clearly marked out. However, in the rainy season, the steep slopes can become slippery and dangerous.

The trail begins in Baker Hill in the same place as the dry waterfall hiking trail, although the two head off in different directions.

5. The Cot

This trail is an easy walk of only 1.6 miles, taking a walker around 1.5 hours to complete at a steady pace. You’ll pass through the valley between the two largest mountains on the island, discovering natural streams that run down from the mountain tops.

It’s a good way to walk off that large lunch.

6. The Underwood

The Underwood trail is a section of the dry waterfall longer hike that can be taken by people who wish to take a safer road, especially in wet weather for inexperienced hikers. The trail takes you through the forest and out onto the sandy shores, though it bypasses the petroglyphs that you’d see on the dry waterfall trail. It’s a great route to take if you aren’t sure you’ll make the longer walks.

7. The Katy Hill Trail

This trail is the most extreme on the island, recommended for only experienced hikers. You’ll continue from beach level, up through mountains with paths covered with thick brush. The whole trail takes you deep into the island, providing a true back to nature feel.

The trail takes approximately 2 hours with a guide, and you should wear long pants and hiking footwear.

8. Jack Boy Hill

The Jack Boy Hill hike takes you right to the top of the mountains with extreme pathways and difficult terrain. Although the hike is only 0.4 miles long, this hike can take up to 2 hours depending on the conditions.

It’s worth it though, with views of the volcano and its disruption laid out before you once you reach the top.

9. Duberry-Cassava

The Duberry-Cassava trail is the best option for wining down and relaxing. It’s a 45-minute light trail that crosses from the coast along the edge of the rainforest for views of the beautiful coastline and stunning wildlife all at the same time.