Bannerman Castle overlook

The island, long known as Pollepel, lies in the ancestral homeland of the Lenape and the Wappinger peoples of the lower Hudson. In the early twentieth century it was bought by Francis Bannerman, a Scottish-born New York dealer who had grown rich buying up surplus arms and military goods, including vast lots left over from the Spanish-American War.

His Manhattan store overflowed, and the law grew nervous about so much powder and munitions in the city, so Bannerman built himself an island arsenal upriver. He designed it in the romantic style of a Scottish castle, with turrets, crenellations, and his company name spelled out large on the walls, part storehouse and part advertisement visible to every passing train and boat.

Bannerman died before his castle was finished, and work largely stopped. A powder explosion damaged part of it, and over the following decades the abandoned buildings decayed. A major fire in the late twentieth century gutted much of what remained, leaving the hollow, roofless shell that stands today.

The state came to own the island, and for years it sat off-limits and slowly crumbling. In recent times a trust has worked to stabilize the ruins and open the island to guided boat and walking tours in the warm season, so the castle that generations saw only from the train can now be visited up close, carefully, among its unstable walls.

The classic view of the castle comes not from the island but from above. The Breakneck Ridge trail climbs the steep eastern wall of the highlands in a series of rocky scrambles, and from its lower ledges hikers look straight down onto Pollepel Island and its ruined castle set in the wide silver river.

It is one of the most popular and most demanding hikes in the region, a hands-on scramble up bare rock that rewards the effort with sweeping views up and down the Hudson gorge. The trailhead sits right beside a Metro-North station, so many hikers ride the train up from the city and step off almost at the base of the climb.

The castle sits in the heart of the Hudson Highlands, the narrow, mountain-walled stretch where the river slices through hard rock, the same dramatic gorge that inspired the painters of the Hudson River School. The riverside towns of Beacon and Cold Spring nearby give the area a lively mix of art, hiking, and history.

Spring and fall are the finest times to walk the ridge and see the island, spring for its green flush and fall for the blaze of color across the highlands. Summer is warm and busy on the trails, and winter strips the ruins bare against the bones of the mountains, though the island tours run only in the warmer months.

The closest Boutel™ stays, so you can turn this stop into an overnight. Each is an independently owned, editorially selected place to stay.