In the breathtaking Hudson Valley, the region’s scenic beauty is forever entwined in a graphic tapestry of history and culture. It’s virtually impossible to avoid history anywhere near the Hudson River; there are so many remnants, wrecks, and ruins to explore. From early settler stone fences to abandoned hotels to modern-era aircraft crash sites, there is no shortage of fantastic destinations for hikers at every ability level. So, lace up your boots, grab your backpack, and let’s discover the history and culture of the Hudson Valley–one hike at a time.
Cornish Estate Trail
Trailhead Location: Garrison, NY
Hike Length: 1.8 miles round trip
Total Ascent: 190 feet
Time: 1 hour
Intensity: Easy
Source: https://mountain-hiking.com/cornish-estate-northgate-ruins/
This might be the easiest hike in the Hudson Highlands, and it’s short! Now in ruins, the estate was originally owned by Sigmund Stern, a diamond merchant, who in 1910 snapped up 650 acres of land and later built a grand house there in the Tudor revival style. In 1916, Edward J. Cornish and his wife Selina became the new owners, and it was during their ownership that the estate became the “Cornish Estate”.
Signs posted around the property read:
“Popularly known as the “Cornish Estate”, the ruins seen here were built by NYC diamond merchant Sigmund Stern in the early 1910’s. The buildings and surrounding 650 acres were inhabited by Edward and Selina Cornish from 1916-1938, when both died within two weeks of each other. A fire in 1958 destroyed most of the mansion. The property became part of the Hudson Highlands State Park in the late 1960’s after a failed attempt by Central Hudson Gas and Electric to turn the property into a power plant.”
Today, the ruins of the mansion, outbuildings, and gardens, all set against the natural beauty of the Hudson Highlands, make the Cornish Estate a fascinating destination and offer a distinctive glimpse into the past.
Close by, on the western banks of the Hudson River, is Storm King Mountain which has many super-scenic trails—and which played a pivotal role in the birth of the environmental movement in the United States. Its story is closely linked to a prolonged legal battle known as the “Storm King Case” which catalyzed public interest in environmental preservation and led to significant new environmental legislation.
Rochester Hollow
Trailhead Location: Big Indian, NY
Hike Length: Choose from 3.5 mile / 4.7 mile / 6.1 mile out-and-back hikes
Total Ascent: 1,000 feet
Time: 3.5 hours
Intensity: Easy to Moderate Hiking
Source: https://mountain-hiking.com/rochester-hollow/
Day hikers, trail-runners, animal track lovers, and New York history buffs will love this especially beautiful triad of interconnected trails just off Route 28, about 40 minutes from the Kingston exit (19) on I-87.
The first 1.75 miles of trail, all the way to the first junction, is on an old road that’s been made ADA compliant; it’s wide and flat and suitable for people with mobility issues. It runs parallel to a gorgeous mountain brook that flows from the back of the hollow.
The back of the hollow is packed with fascinating destinations.
Starting at the first junction the Burroughs Memorial Trail loops through historically farmed land where many impressive stone fences remain standing. These are the tallest and the most intact stone walls I’ve seen in the Catskills…
You can also visit the foundation of an old maple sap house…
At the next junction, turn right to head west, and you’ll pass this remnant of a garage used for carriages on the Colonel Rochester Trail. At a junction, the trail converts to the Eignor Trail which winds through a meadow and undulating terrain that trail runners will love. This 1.35 mile trail loops back around to the east and re-connects with the main Colonel Rochester Trail. Just before the turn south, you can visit the Burroughs Memorial on the left side of the trail. Burroughs was the literary naturalist who put the Catskills on the map as a destination. The Hudson River School of painters were also responsible, but it was Burroughs’s writing that drew to his cause the likes of Theodore Roosevelt, John Muir, Henry Ford, Harvey Firestone, Thomas Edison, and Walt Whitman.
For overnight wilderness camping, there are also two primitive camping spots near the brook within the first 1000 feet or so of the trailhead. At the back of the hollow, a lean-to shelter provides an even deeper wilderness experience for overnighters. In winter, cross-country skiers and snowshoers make sure these trails are well-loved all year round.
Who Was Colonel Rochester?
Nathaniel Rochester was the founder of the settlement that would later become Rochester, New York. He was a significant figure during his era, with a range of roles including a prosperous businessman, a military leader, a political strategist, and a land speculator. Additionally, historical records show that Rochester was involved in the institution of slavery, both as an owner and trader. The trading of enslaved people during this period was a complex but common operation that now appalls us.
Doodletown
Trailhead Location: Philipstown, NY
Hike Length: 3 miles
Total Ascent: 530 feet
Time: 2 hours
Intensity: Easy
Source: https://www.alltrails.com/trail/us/new-york/doodletown-1777-trail-short-loop
Doodletown is a former settlement in Rockland County, now a part of Bear Mountain State Park in the Hudson Highlands. The hamlet, now considered a “ghost town,” has a rich history that dates back to the 18th century.
The area was settled in the mid-1700s, primarily by English, Dutch, and Hessian immigrants. By the late 19th century, Doodletown had grown into a small, thriving community with homes, churches, schools, and businesses, including a mining operation in the nearby Dunderberg Mountain.
However, by the mid-20th century, the town began to decline. Today, Doodletown is a popular destination for hikers and history enthusiasts, filled with superb stone staircases and the shells of long-abandoned homes. Nature has reclaimed much of the area, but remnants of the former community, including stone foundations, steps, wells, and a cemetery, are still visible.
Interpretive signs along the trails provide information about the town’s history and the families that once lived there. Doodletown’s story serves as a reminder of the complex interplay between human settlement, conservation, and land use in natural areas. Scars from the short-term industries of the 1700s and 1800s remain all over the Hudson Valley.
The Fried Chicken War and the Grand Hotels of the Catskills
Trailhead Location: Laurel House Trailhead, Palenville, NY
Hike Length: 3.6 miles
Total Ascent: 560 feet
Time: 2 hours
Intensity: Easy
Source: Route via GaiaGPS
In the late 19th century, a famous rivalry exploded between two iconic hotels in the Catskills: the Catskill Mountain House and the Hotel Kaaterskill. The story behind their rivalry began in 1880 when George Harding, a prominent Philadelphia businessman and lawyer, visited the Catskill Mountain House. While dining at the hotel, Harding tried to order fried chicken for his daughter Emily. Unfortunately, the hotel’s menu for the day featured roast beef—chicken was not available. This seemingly trivial incident sparked a heated exchange between Harding and the hotel staff, eventually involving the owner, Charles Beach.
Unable to resolve the dispute, Beach suggested that Harding build his own hotel if he wanted fried chicken so much. Harding immediately checked his family out of the Catskill Mountain House and, by the following year, in 1881, the Hotel Kaaterskill was opened on the summit of South Mountain, directly competing with and completely overshadowing the Catskill Mountain House.
From its inception, the Hotel Kaaterskill was an impressive feat, boasting beds for 612 guests. In 1883, an annex was added, further expanding its capacity to nearly 1,100 guests. At the time, the New York Times described it as, “a city in itself”. It even had its own zip code. The rivalry between Beach and Harding—known as “The Fried Chicken War”—endured until both men passed away in 1902.
The feud left a lasting legacy in the Catskills’ history and became a notorious tale of Capitalist competition. The Hotel Kaaterkill burned to the ground on September 8, 1924 and, as the era of lavish mountaintop hotels had passed, it was never rebuilt.
Today, visitors can explore what’s left of the Hotel Kaaterskill—some foundations, a large stone cister which can be accessed via a short loop trail off of the terminus of Schutt Road Trail (red blazes) on South Mountain in the Catskills.
You can also visit nearby Inspiration Point, one of the most breathtaking scenic spots in the Catskills.
Overlook Mountain House Ruins
Trailhead Location: Woodstock, NY
Hike Length: 3.5 miles
Total Ascent: 1,135 feet
Time: 2-3 hours
Intensity: Moderate
Source: https://mountain-hiking.com/overlook-sunrise/
The Overlook Mountain House ruins are one of the most popular day-hike destinations in the Catskills. The ruins are imposing, intriguing, grand, and grim—especially spooky in fog.
This trail follows an old road, so it’s mostly wide and even and very easy to follow. It’s also relentlessly uphill and a little steep in spots.
At 1.6 miles, look to your right for an opening into the woods. The ruins are hard to miss. Fires burned down two previous incarnations of the hotel, which was almost rebuilt, but the project ran out of funding, was abandoned, and now its glorious ruins are being reclaimed by nature.
You can visit the main ruins, which are spectacularly photogenic, but there’s also a second building close by, Overlook Lodge, which was used by the owner’s family.
From the ruins, you can also continue on to Overlook Mountain’s ledge and fire tower with their jaw-dropping views of the Hudson Valley and the surrounding Catskills High peaks. This would bring your hike length total to 4.5 miles and 1,325 feet of elevation gain.
