5 Hudson Valley Hiking Trails Filled With History and Ruins

These five trails offer a step back in time. They're dotted with old estates, mines, and other remains of the day.

In search of hiking trails that offer something more than scenic views and picturesque terrain in the Hudson Valley? These trails play host to history and ruins, with difficulty levels to suit every style of hiker.

Overlook Mountain Trail / Woodstock

Difficulty: moderate to challenging
Length: 4.6 miles
Route Type: out & back

Prepare for a workout with a big payoff—the opportunity to view the ruins of a once-grand hotel and a fire tower that offer stunning views of the Catskills. After ascending 1,160 feet and nearing the summit, you’ll come across the remains of the Overlook Mountain House, a 19th-century resort that burned down twice in 1875 and 1921. The owner constructed a concrete frame for the final rebuild but never completed the hotel—it was sold to the state Department of Environmental Conservation in 1940.

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The Overlook Mountain House ruins in Woodstock.
The Overlook Mountain House ruins in Woodstock. Courtesy of Ulster County Tourism.

Cornish Estate Trail / Cold Spring

Difficulty: easy
Length: 1.8 miles
Route Type: out & back

Considered one of the easiest hikes in Hudson Highlands State Park, the Cornish Estate Trail is mostly comprised of an old concrete road with a very light incline. The route leads to the Cornish Estate, built in 1910 by diamond merchant Sigmund Stern. Edward and Selina Cornish bought the property in 1916; it was left abandoned after their deaths in 1938 and burned down in 1958. The hike out won’t take long, giving you time to explore the skeletal stone remains of the home, swimming pool, and greenhouse.

Sterling Lake in Tuxedo Park
Sterling Lake in Tuxedo Park. Courtesy Ulster County Tourism.

Sterling Lake Loop Trail / Tuxedo Park

Difficulty: easy
Length: 4.2 miles
Route Type: loop

This leisurely hike circles Sterling Lake and offers picturesque water views and several remnants from the now-defunct Sterling Lake Iron Works, which extracted iron ore from 1751 to 1891. The mines today are flooded, but a stone furnace, ore crusher, and hoist house still stand. At the end of the loop, you can hike an additional 1.5-mile out-and-back to see the fire tower, which has a picnic area at the base. Don’t miss the visitor center near the trailhead, which has nature and history displays, plus an interactive trail map.

Sterling Lake Loop Trail.
Sterling Lake Loop Trail. Photo by Francesca Furey.

Mount Beacon / Beacon

Difficulty: moderate to challenging
Length: 3.7 miles
Route Type: out & back

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Once a booming area for tourists to stay and gamble, these days the summit of Mount Beacon attracts hikers who want a glimpse of the Mount Beacon Casino and Beaconcrest Hotel, built in 1902 and 1908, respectively. Both caught fire in 1927, and the incline railway that transported guests up the mountain ceased operations in 1978. The Casino Trail (red blazes) is the most popular route and will bring you past the ruins to a fire tower. Prepare for a climb—the trail’s elevation gain is nearly 1,400 feet.

Cedar Glen at Franny Reese State Park in Highland.
Cedar Glen at Franny Reese State Park in Highland. Photo by Francesca Furey

Franny Reese State Park / Highland

Difficulty: easy
Length: 1.76 (white) or 3.9 miles (white and yellow)
Route Type: out & back, loop

With several trail options, you can hike straight to the ruins or take the scenic route. The yellow trail (which connects to both parking lots) brings you to the remnants of Cedar Glen, the 19th-century estate of Poughkeepsie dentist Charles H. Roberts; then take the white trail loop for vistas of the Hudson River, Poughkeepsie, the Mid-Hudson Bridge, and the Walkway Over the Hudson.

Related: Hiking in the Catskills: A Beginner’s Guide to Hudson Valley Treks

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