The Leinster Bay Trail entrance starts at the foot of the hill leading to the Annaberg Plantation Ruins, just east of the parking area. Just after you pass the sandy beach at Waterlemon – the trail splits. Stay to the left to continue out to a point closest to Waterlemon Cay. Take the narrow trail to the right and you’re on the northern end of the Johnny Horn Trail.
A short hike up this trail leads to two sets of ruins. Both a worth the minimal effort required to see some amazing St John history and stunning views of Leinster Bay, Waterlemon Cay and the BVIs.
The first set of ruins is the Old Danish Guardhouse. Located approximately a hundred yards beyond the fork in the trail – you’ll find a wonderful stone arch and stone walls that once formed a Danish Colonial overlook. From this vantage point Danish soldiers could watch ships that passed through the channel; and keep an eye out for boats that came and went from the Annaberg Plantation in Leinster Bay.
The second set of ruins, Windy Hill, is a couple of hundred yards up the trail. Continue past the Danish Guardhouse ruins. The trail narrows and becomes a bit steeper. But trust us, it’s worth the hike just for the view! Look for the first trail that leads off to your left (toward the water). Follow this trail a short distance until you reach the Windy Hill ruins. Located on a rocky knoll that sits high above Waterlemon Cay. From here you can enjoy one of St John’s most amazing views! To your left as you face the water is Annaberg. You’ll look across Leinster Bay to Mary Point. Below you is Waterlemon Cay. And look to the north-east and you’ll see the island of Tortola in the British Virgin Islands.