Historical past Hikes: 5 Native Hikes with Ruins…and a REALLY Good Story

Within the breathtaking Hudson Valley, the area’s scenic magnificence is endlessly entwined in a graphic tapestry of historical past and tradition. It’s nearly unimaginable to keep away from historical past wherever close to the Hudson River; there are such a lot of remnants, wrecks, and ruins to discover. From early settler stone fences to deserted motels to modern-era plane crash websites, there isn’t a scarcity of implausible locations for hikers at each means stage. So, lace up your boots, seize your backpack, and let’s uncover the historical past and tradition of the Hudson Valley–one hike at a time.
Cornish Property Path
Trailhead Location: Garrison, NY
Hike Size: 1.8 miles spherical journey
Complete Ascent: 190 ft
Time: 1 hour
Depth: Simple
Supply: https://www.alltrails.com/path/us/new-york/cornish-trail-to-breakneck-brook
This could be the simplest hike within the Hudson Highlands, and it’s quick! Now in ruins, the property was initially owned by Sigmund Stern, a diamond service provider, who in 1910 snapped up 650 acres of land and later constructed a grand home there within the Tudor revival model. In 1916, Edward J. Cornish and his spouse Selina grew to become the brand new house owners, and it was throughout their possession that the property grew to become the “Cornish Property”.
Photograph by Sean O’Dwyer
Exterior ruins of the Cornish Property, close to Chilly Spring, New York.
Indicators posted across the property learn:
“Popularly referred to as the “Cornish Property”, the ruins seen right here had been constructed by NYC diamond service provider Sigmund Stern within the early 1910’s. The buildings and surrounding 650 acres had been inhabited by Edward and Selina Cornish from 1916-1938, when each died inside two weeks of one another. A fireplace in 1958 destroyed a lot of the mansion. The property grew to become a part of the Hudson Highlands State Park within the late 1960’s after a failed try by Central Hudson Gasoline and Electrical to show the property into an influence plant.”
As we speak, the ruins of the mansion, outbuildings, and gardens, all set towards the pure great thing about the Hudson Highlands, make the Cornish Property a captivating vacation spot and supply a particular glimpse into the previous.

Photograph by Sean O’Dwyer
Inside ruins of the Cornish Property.
Shut by, on the western banks of the Hudson River, is Storm King Mountain which has many super-scenic trails—and which performed a pivotal position within the beginning of the environmental motion in america. Its story is carefully linked to a chronic authorized battle referred to as the “Storm King Case” which catalyzed public curiosity in environmental preservation and led to vital new environmental laws.
Rochester Hole
Trailhead Location: Large Indian, NY
Hike Size: Select from 3.5 mile / 4.7 mile / 6.1 mile out-and-back hikes
Complete Ascent: 1,000 ft
Time: 3.5 hours
Depth: Simple to Reasonable Climbing
Supply: https://mountain-hiking.com/rochester-hollow/
Day hikers, trail-runners, animal monitor lovers, and New York historical past buffs will love this particularly stunning triad of interconnected trails simply off Route 28, about 40 minutes from the Kingston exit (19) on I-87.
The primary 1.75 miles of path, all the way in which to the primary junction, is on an outdated highway that’s been made ADA compliant; it’s large and flat and appropriate for individuals with mobility points. It runs parallel to a beautiful mountain brook that flows from the again of the hole.
The again of the hole is full of fascinating locations.
Beginning on the first junction the Burroughs Memorial Path loops by way of traditionally farmed land the place many spectacular stone fences stay standing. These are the tallest and essentially the most intact stone partitions I’ve seen within the Catskills…
You may as well go to the inspiration of an outdated maple sap home…

Photograph by Sean O’Dwyer
Maple sap home foundations
On the subsequent junction, flip proper to go west, and also you’ll move this remnant of a storage used for carriages on the Colonel Rochester Path. At a junction, the path converts to the Eignor Path which winds by way of a meadow and undulating terrain that path runners will love. This 1.35 mile path loops again round to the east and re-connects with the primary Colonel Rochester Path. Simply earlier than the flip south, you possibly can go to the Burroughs Memorial on the left facet of the path. Burroughs was the literary naturalist who put the Catskills on the map as a vacation spot. The Hudson River Faculty of painters had been additionally accountable, however it was Burroughs’s writing that drew to his trigger the likes of Theodore Roosevelt, John Muir, Henry Ford, Harvey Firestone, Thomas Edison, and Walt Whitman.

Photograph by Sean O’Dwyer
Remnant of a storage used for carriages, on Colonel Rochester Path
For in a single day wilderness tenting, there are additionally two primitive tenting spots close to the brook throughout the first 1000 ft or so of the trailhead. In the back of the hole, a lean-to shelter offers a fair deeper wilderness expertise for overnighters. In winter, cross-country skiers and snowshoers be certain these trails are well-loved all yr spherical.
Who Was Colonel Rochester?
Nathaniel Rochester was the founding father of the settlement that will later change into Rochester, New York. He was a big determine throughout his period, with a spread of roles together with a affluent businessman, a navy chief, a political strategist, and a land speculator. Moreover, historic information present that Rochester was concerned within the establishment of slavery, each as an proprietor and dealer. The buying and selling of enslaved individuals throughout this era was a fancy however frequent operation that now appalls us.
Doodletown
Trailhead Location: Philipstown, NY
Hike Size: 3 miles
Complete Ascent: 530 ft
Time: 2 hours
Depth: Simple
Supply: https://www.alltrails.com/path/us/new-york/doodletown-1777-trail-short-loop
Doodletown is a former settlement in Rockland County, now part of Bear Mountain State Park within the Hudson Highlands. The hamlet, now thought of a “ghost city,” has a wealthy historical past that dates again to the 18th century.
The world was settled within the mid-1700s, primarily by English, Dutch, and Hessian immigrants. By the late nineteenth century, Doodletown had grown right into a small, thriving neighborhood with houses, church buildings, faculties, and companies, together with a mining operation within the close by Dunderberg Mountain.
Nevertheless, by the mid-Twentieth century, the city started to say no. As we speak, Doodletown is a well-liked vacation spot for hikers and historical past fans, crammed with very good stone staircases and the shells of long-abandoned houses. Nature has reclaimed a lot of the world, however remnants of the previous neighborhood, together with stone foundations, steps, wells, and a cemetery, are nonetheless seen.
Interpretive indicators alongside the paths present details about the city’s historical past and the households that when lived there. Doodletown’s story serves as a reminder of the complicated interaction between human settlement, conservation, and land use in pure areas. Scars from the short-term industries of the 1700s and 1800s stay all around the Hudson Valley.
The Fried Rooster Warfare and the Grand Inns of the Catskills
Trailhead Location: Laurel Home Trailhead, Palenville, NY
Hike Size: 3.6 miles
Complete Ascent: 560 ft
Time: 2 hours
Depth: Simple
Supply: Route by way of GaiaGPS
Within the late nineteenth century, a well-known rivalry exploded between two iconic motels within the Catskills: the Catskill Mountain Home and the Resort Kaaterskill. The story behind their rivalry started in 1880 when George Harding, a outstanding Philadelphia businessman and lawyer, visited the Catskill Mountain Home. Whereas eating on the lodge, Harding tried to order fried rooster for his daughter Emily. Sadly, the lodge’s menu for the day featured roast beef—rooster was not obtainable. This seemingly trivial incident sparked a heated alternate between Harding and the lodge employees, ultimately involving the proprietor, Charles Seaside.
Unable to resolve the dispute, Seaside steered that Harding construct his personal lodge if he needed fried rooster a lot. Harding instantly checked his household out of the Catskill Mountain Home and, by the next yr, in 1881, the Resort Kaaterskill was opened on the summit of South Mountain, straight competing with and utterly overshadowing the Catskill Mountain Home.

Photograph by Sean O’Dwyer
Facade of Resort Kaaterskill.
From its inception, the Resort Kaaterskill was a formidable feat, boasting beds for 612 company. In 1883, an annex was added, additional increasing its capability to just about 1,100 company. On the time, the New York Instances described it as, “a metropolis in itself”. It even had its personal zip code. The rivalry between Seaside and Harding—referred to as “The Fried Rooster Warfare”—endured till each males handed away in 1902.
The feud left an enduring legacy within the Catskills’ historical past and have become a infamous story of Capitalist competitors. The Resort Kaaterkill burned to the bottom on September 8, 1924 and, because the period of lavish mountaintop motels had handed, it was by no means rebuilt.
As we speak, guests can discover what’s left of the Resort Kaaterskill—some foundations, a big stone cister which may be accessed by way of a brief loop path off of the terminus of Schutt Street Path (purple blazes) on South Mountain within the Catskills.
You may as well go to close by Inspiration Level, one of the vital breathtaking scenic spots within the Catskills.
Overlook Mountain Home Ruins
Trailhead Location: Woodstock, NY
Hike Size: 3.5 miles
Complete Ascent: 1,135 ft
Time: 2-3 hours
Depth: Reasonable
Supply: https://mountain-hiking.com/overlook-sunrise/
The Overlook Mountain Home ruins are one of the vital well-liked day-hike locations within the Catskills. The ruins are imposing, intriguing, grand, and grim—particularly spooky in fog.

Photograph by Sean O’Dwyer
Exterior Overlook Mountain Home in summer time
This path follows an outdated highway, so it’s largely large and even and really straightforward to observe. It’s additionally relentlessly uphill and slightly steep in spots.

Photograph by Sean O’Dwyer
Inside Overlook Mountain Home in winter
At 1.6 miles, look to your proper for a gap into the woods. The ruins are arduous to overlook. Fires burned down two earlier incarnations of the lodge, which was virtually rebuilt, however the venture ran out of funding, was deserted, and now its wonderful ruins are being reclaimed by nature.
You may go to the primary ruins, that are spectacularly photogenic, however there’s additionally a second constructing shut by, Overlook Lodge, which was utilized by the proprietor’s household.

Photograph by Sean O’Dwyer
Exterior Overlook Lodge
From the ruins, it’s also possible to proceed on to Overlook Mountain’s ledge and fireplace tower with their jaw-dropping views of the Hudson Valley and the encircling Catskills Excessive peaks. This could deliver your hike size whole to 4.5 miles and 1,325 ft of elevation achieve.