Ultimate Guide to the Best Horseback Riding in St. John

Discovering the beauty of St. John on horseback is a unique adventure that speaks to both the heart and soul. The island, known for its vibrant scenery and rich history, offers trails that cater to riders of all skill levels. From peaceful beach views to rugged mountainous paths, the landscapes you encounter will leave you in awe. Join us as we explore 25 of the best horseback riding trails on St. John, each showcasing stunning visuals that are sure to impress.

Travel Guide: St John

1. Cinnamon Bay Trail

Wide angle view of Cinnamon Bay at sunset — Cinnamon Bay Trail with its stunning sunset view

The Cinnamon Bay Trail shines with stunning views of one of St. John’s most popular beaches. As you ride along this scenic path, the vibrant turquoise waters sparkle in the sunlight. This beginner-friendly trail stretches about two miles and is perfect for a leisurely ride. Riders can enjoy encountering tropical plants and a variety of wildlife, such as brown pelicans and iguanas, that make this trail truly special.

2. Francis Bay Trail

Eye-level view of Francis Bay with the mountains in the background — Francis Bay Trail with scenic mountains

The Francis Bay Trail winds through a rich ecosystem of coral reefs and mangroves. This short trail, about 1.5 miles long, is bursting with biodiversity, offering sightings of local bird species such as the Great Egret and hummingbirds. The gentle pace of this trail allows riders to appreciate the beautiful harmony of land and sea.

3. Maho Bay Trail

High angle view of Maho Bay with clear waters and sandy beach — Maho Bay Trail showcasing the clear waters

The Maho Bay Trail is perfect for those who seek tranquility. This 2-mile trail offers breathtaking viewpoints that overlook the calm waters of Maho Bay, a favorite spot for both tourists and locals for swimming and snorkeling. Riders here can take in the breathtaking sunsets and enjoy the peaceful environment.

4. Ram Head Trail

Dramatic view of the rocky cliff at Ram Head — Ram Head Trail with rocky cliffs

Located at the southern tip of St. John, the Ram Head Trail presents a tougher ride with rocky terrain. This roughly 2-mile route rewards intermediate riders with stunning panoramic views of the Caribbean Sea, including the Virgin Islands in the distance. It’s an exhilarating experience that captures the spirit of adventure.

5. Reef Bay Trail

Close-up view of the lush foliage along Reef Bay Trail — Reef Bay Trail with rich foliage

The Reef Bay Trail stands out for its historical significance, showcasing ancient rock carvings, which are remnants from the Taino people. This 3-mile trail offers a glimpse into St. John’s culture while enjoying its enchanting natural surroundings. Riders can learn about the island’s history while seeing various plant species, creating a memorable experience.

6. Bordeaux Mountain Trail

High angle view of Bordeaux Mountain surrounded by greenery — Bordeaux Mountain Trail with lush mountains

The Bordeaux Mountain Trail leads you to St. John’s highest point. This challenging 2-mile trail is best suited for seasoned riders looking for adventure. The effort taken to reach the summit is rewarded with breathtaking views of the island and surrounding waters—an experience that should not be missed.

7. Cinnamon Bay to Annaberg Trail

Wide angle view of Annaberg plantation ruins — Cinnamon Bay to Annaberg Trail featuring plantation ruins

Connecting Cinnamon Bay to the historic Annaberg Plantation, this 3-mile trail offers an enriching look into the island’s colonial past. Riders can view the remnants of sugar cane ruins and other artifacts, providing a remarkable historical context to the ride.

8. Caneel Bay Trail

Close-up view of the tranquil waters of Caneel Bay — Caneel Bay Trail overlooking tranquil waters

The Caneel Bay Trail is known for its easy navigation, making it perfect for riders of all skill levels. Spanning approximately 1.5 miles, this trail offers stunning coastal views and vibrant flora. Families and leisure riders often choose this trail for its calming ride and breathtaking scenery.

9. Little Cinnamon Bay Trail

High angle view of Little Cinnamon Bay with its crystal clear waters — Little Cinnamon Bay Trail showcasing clear waters

Slightly off the beaten path, the Little Cinnamon Bay Trail provides a peaceful escape. This 1.5-mile trail leads riders through tranquil beaches and lush vistas, perfect for those looking to enjoy a quieter experience away from crowded tourist spots.

10. East End Trail

Wide angle view of the East End landscape showing rugged cliffs — East End Trail with rugged cliffs

The East End Trail is an invigorating route that offers challenges through rugged cliffs and serene shorelines. Covering around three miles, this trail presents stunning views of the coastline, rewarding adventurous riders with captivating scenery.

11. Peace Hill Trail

Close-up view of the historic ruins at Peace Hill — Peace Hill Trail with historic ruins

The Peace Hill Trail provides an excellent mix of historical allure and natural beauty. This 2-mile trail leads riders to some of St. John’s most stunning lookout points, where they can connect with the island’s past while enjoying breathtaking vistas.

12. Fish Bay Trail

Eye-level view of the tranquil Fish Bay surrounded by greenery — Fish Bay Trail showcasing tranquil surroundings

Fish Bay Trail is perfect for those who appreciate a peaceful, nature-filled environment. This 2-mile trail features a relaxing ride through lush greenery, where the beauty of the bay creates a tranquil atmosphere for riders.

13. Concordia Trail

Wide angle view of the mountain landscape along Concordia Trail — Concordia Trail with breathtaking mountain views

Famous for its mountain views, the Concordia Trail stretches about two miles. Riders can enjoy a meandering path offering a higher vantage point of St. John’s stunning landscapes, perfect for taking memorable photographs.

14. Brown Bay Trail

High angle view of the scenic Brown Bay coastline — Brown Bay Trail featuring scenic coastline

The Brown Bay Trail is a quieter route leading to one of St. John’s lesser-known beaches. This 1.5-mile path showcases lush flora and stunning coastal views. It’s ideal for riders seeking peaceful scenery away from more populated areas.

15. Waterlemon Trail

Eye-level view of the stunning Waterlemon Cay and surrounding waters — Waterlemon Trail with picturesque cay

Waterlemon Trail is a delightful 2-mile route leading riders through extraordinary landscapes to the beautiful Waterlemon Cay. This spot is perfect for those who appreciate scenic adventures, as the views are particularly enchanting, making for an unforgettable ride.

16. Lameshur Bay Trail

Close-up view of Lameshur Bay surrounded by nature — Lameshur Bay Trail showcasing natural beauty

The Lameshur Bay Trail combines mountain views with fresh sea breezes. Approximately two miles long, this route offers diverse scenery, allowing riders to immerse themselves in St. John’s remarkable natural beauty.

17. Coral Bay Trail

Wide angle view of Coral Bay with its vibrant waters — Coral Bay Trail featuring vibrant waters

Coral Bay Trail provides stunning views of the vibrant Coral Bay area. Covering just over two miles, the trail features winding paths suitable for riders at different skill levels. Take time to observe local wildlife, such as colorful fish and seabirds, during your ride.

18. Fish Bay to Drunk Bay Trail

High angle view of Drunk Bay's unique rock formations — Fish Bay to Drunk Bay Trail showcasing unique rock formations

This trail leads you through picturesque landscapes to the fascinating rock formations of Drunk Bay. At approximately three miles long, it offers a moderate challenge suitable for those seeking diverse scenery while enjoying a leisurely ride.

19. Virgin Islands National Park Trail

Close-up view of scenic landscapes within Virgin Islands National Park — Virgin Islands National Park Trail featuring lush landscapes

The trails within Virgin Islands National Park are a breathtaking collection of stunning views and diverse ecosystems. Offering various routes for all skill levels, riders can truly immerse themselves in St. John’s captivating nature.

20. Bordeaux Trail

Eye-level view of Bordeaux's rich foliage and hills — Bordeaux Trail showcasing lush foliage

Bordeaux Trail features a winding path through lush foliage and rolling hills, making it accessible for beginners and experienced riders alike. About two miles long, it brings numerous surprises and enjoyable sights along the way.

21. Chocolate Hole Trail

Wide angle view of Chocolate Hole and surrounding vistas — Chocolate Hole Trail overlooking tranquil waters

This enchanting trail along Chocolate Hole offers beautiful views of the bay. Perfect for families, the 1.5-mile path provides a relaxing ride surrounded by scenic tranquility, allowing riders to unwind and enjoy the surroundings.

22. Lind Point Trail

High angle view of Lind Point's picturesque coastal views — Lind Point Trail showcasing coastal views

The Lind Point Trail, stretching 1.5 miles from Cruz Bay, invites riders to experience captivating coastal views and vibrant beaches. This trail is ideal for all riding levels, providing an excellent opportunity to take in the island’s natural beauty.

23. Estate Hope Trail

Close-up view of Estate Hope’s lush greenery — Estate Hope Trail featuring lush greenery

The Estate Hope Trail encompasses historical areas filled with beautiful tropical flora. Spanning 1.8 miles, this unique route blends cultural heritage with stunning nature, making for an engaging riding experience.

24. Great Cruz Bay Trail

Eye-level view of the tranquil waters at Great Cruz Bay — Great Cruz Bay Trail with stunning tranquility

At about two miles long, the Great Cruz Bay Trail offers spectacular ocean views. This trail is perfect for leisurely rides, providing a serene experience for families and riders looking to enjoy the peaceful surroundings of St. John.

25. Upper Paul Trail

Wide angle view of Upper Paul Trail set against a vibrant sunset — Upper Paul Trail with vibrant sunset

The Upper Paul Trail offers remarkable views of the Caribbean. Measuring about three miles, this trail provides experienced riders with uneven terrain and stunning visual rewards. It’s perfect for those looking for a challenging yet exhilarating outdoor experience.

Embrace the Beauty of St. John

With an incredible array of horseback riding trails, St. John offers a perfect blend of nature, culture, and adventure. Each of these 25 trails presents its own unique charm—from breathtaking ocean views to rich historical encounters. Whether you are a novice rider or highly skilled, these trails promise to create lasting memories and breathtaking visuals.

So grab your saddle and prepare to explore the hidden gems of St. John, where untouched nature, exciting adventures, and tranquility await you at every turn.

KW Adventure Explorer