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The Hudson Valley and the Catskills

Sleepy Hollow up the river to Woodstock — the Leatherman's grave, a UFO museum, a bluestone quarry turned into a monument, and a castle on an island that its builder never finished.

9 stops · 3 days · New York · roughly 117 miles point to point

See the whole route and everything odd beside it

OddWay draws your route first, then plots every stop that falls inside the detour you're willing to make. No hunting through a list to work out what is actually on the way.

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Every one of the 9 places in the index. Plan a route and the map narrows to what's actually near it.

The Hudson Valley has been generating this material for longer than the country has existed, and unusually, a lot of it is still standing.

Start where the story does

Sleepy Hollow. Washington Irving published the Headless Horseman in 1820, and the valley has been trading on it ever since — but the marker is worth stopping at because the story is genuinely from here rather than attached to it afterwards, which is not true of most American legends.

The Leatherman at Ossining is the better one. A real man who walked a 365-mile circuit through New York and Connecticut in the 1880s in a handmade suit of heavy leather, on a schedule regular enough that households set out food for him. Nobody ever established who he was.

Up the river

The Armour-Stiner Octagon House at Irvington is the only known eight-sided domed Victorian house in the world, which is a specific enough claim to be true.

Bannerman Castle on Pollepel Island is a munitions dealer's fantasy warehouse, built from 1901 and never finished. It burned in 1969 and partly collapsed in 2009. Boat tours only, seasonal — book ahead.

Pine Bush spent the 1980s and 90s as one of the most reported UFO areas in the eastern United States and now has the museum.

The Catskills

The Kaatskill Kaleidoscope at Mount Tremper is built inside a converted grain silo and is the largest in the world.

Overlook Mountain House is a hotel that burned three times; the concrete 1920s attempt was abandoned unfinished and its shell is a two-mile uphill walk from the road.

Opus 40 finishes it: six and a half acres of bluestone that the sculptor Harvey Fite spent thirty-seven years fitting together without mortar. He intended it as a setting for his statues and eventually realised it was the work.

Practical

Three days. Bannerman and Overlook both need planning — one is a boat, the other is a climb.

Autumn is the obvious season and everyone knows it. The valley is quieter and just as good in May.

The Route

  1. Headless Horseman Marker

    Sleepy Hollow, New York

    Sleepy Hollow Cemetery and the adjoining Old Dutch Church landscape are inseparable from Washington Irving's The Legend of Sleepy Hollow. A Legends & Lore marker inside the cemetery specifically commemorates the story that the Headless Horseman tethers his horse among the graves.

  2. The Leatherman Grave and Marker

    Ossining, New York

    The mysterious wanderer known as the Leatherman repeatedly walked a roughly 365-mile circuit through New York and Connecticut in the 1880s while wearing a handmade suit of heavy leather. He died in 1889 and is buried in Ossining, where a Legends & Lore marker records one of New York's strangest real-life folk figures.

  3. Armour-Stiner Octagon House

    Irvington, New York

    This exuberant pink Victorian residence was transformed in the 1870s into an eight-sided domed house inspired by nineteenth-century octagon-house theories. It remains a private residence, and both the house and grounds are accessible only through advance ticketed guided tours.

  4. Bannerman Castle

    Fishkill, New York

    Military-surplus dealer Francis Bannerman built this eccentric castle-like arsenal on Pollepel Island between 1900 and 1918, later leaving a romantic ruin after explosions, fire and abandonment. The island is controlled by New York State Parks and can be visited only through authorized seasonal boat or kayak tours.

  5. Spook Hill

    Wappingers Falls, New York

    Spook Hill Road supposedly earned its name when moonlight reflecting from a rocky hillside created a strange glow that terrified horses traveling the old dirt road. The original landscape has changed considerably, but a 2023 Legends & Lore marker in Spook Hill Park preserves the story.

  6. Pine Bush UFO Museum

    Pine Bush, New York

    The Pine Bush UFO & Paranormal Museum explores the Hudson Valley area's long history of UFO sightings through interactive exhibits, witness accounts, displays and alien-themed experiences. This is clearly a UFO-focused attraction and belongs in the `ufos` category rather than `haunted`.

  7. Kaatskill Kaleidoscope

    Mount Tremper, New York

    The Kaatskill Kaleidoscope is a roughly 60-foot silo converted into an immersive walk-in kaleidoscope at the Emerson Resort in Mount Tremper, not Shokan proper. It opened in 1996, and visitors today buy admission to stand inside while projected imagery and sound transform the silo interior.

  8. Overlook Mountain House Ruins

    Woodstock, New York

    Concrete walls and staircases from the abandoned Overlook Mountain House still stand high above Woodstock after repeated fires and unfinished rebuilding attempts ended the resort's history. The ruins are reached by a steep multi-mile hike, and the state warns visitors not to enter or climb the unstable structures.

  9. Opus 40

    Saugerties, New York

    Sculptor Harvey Fite spent nearly four decades assembling this sprawling bluestone earthwork by hand from millions of pieces of local stone. The six-acre labyrinth of ramps, terraces, walls and platforms is open seasonally as an outdoor arts site.