From the tip of Manhattan to the Adirondacks, the Hudson Valley is an adventurer’s dream, offering some of the toughest hikes on the East Coast that invite exploration, determination, and a test of grit. Trails like Breakneck Ridge, Mount Beacon, the daunting Catskill 9, and the notorious Devil’s Path demand not just physical strength but mental resilience, inviting hikers to step beyond their comfort zones and challenge their limits. Nestled closely to the headwaters of the mighty Hudson River, the climbs of the Santanoni Range add to this rugged tapestry of trails, pushing even seasoned hikers to conquer new heights.
The thrill of these trails—presented in order of increasing difficulty—lies not just in their challenge but in the rich rewards they offer: awe-inspiring vistas, a deep sense of accomplishment, and a distinct way to connect with the landscape of the Hudson Valley. So strap on your boots, pack your 10 Essentials, and set your sights high; it’s time to tackle the toughest trails the Hudson Valley has to offer.
Beacon Mountain Fire Tower
Trailhead Location: Wolcott Avenue, Beacon
Hike Length: 3.9 miles
Total Ascent: 1,400 feet
Time: 2-3 hours
Intensity: Strenuous
Well-known in the area as a workout hike, the first mile of the Mount Beacon Casino Trail is relentlessly steep. It begins with a zigzagging metal staircase consisting of about 200 steps. At the top of the stairs, the steep trail continues along rugged switchbacks that eventually take you to the ruins of a defunct incline railway’s powerhouse. (The funicular railway ran from 1903 to 1978 and was a major tourist attraction for the area.) Nearby, the foundation of an old dance hall (the “casino”) provides an enormous flat viewing area above the town of Beacon and the Hudson River below. From here, another mile of trail brings you to Mount Beacon’s fire tower which has one of the grandest views in the Hudson Highlands. From there, you can return the way you came or continue in a loop around Beacon Reservoir via Schofield Ridge, which offers many more views of the surrounding highlands. After your hike, there are also so many options in Beacon for a solid chew-and-chat.
Breakneck Ridge
Trailhead Location: Roadside Parking on 9D, Beacon
Hike Length: 3 miles
Total Ascent: 1,300 feet
Time: 3 hours
Intensity: Difficult
Close-by Breakneck Ridge has long been regarded as the toughest hike in the Hudson Highlands. Its vertiginous rock scrambles will test your coordination and your nerves. The trail begins at sea level and scrambles up 1,100 feet in less than three-quarters of a mile, which is steeper than any hiking trail in the Catskills. But it’s so fun. And those views!
Due to its difficult, technical scrambles, this trail is not recommended for pets. Hikers should be in good physical condition, as prolonged effort is required. Fitness freaks will gobble up this route, but regular people will find it extremely taxing.
By the way, you’ll find Metro North train stations close to both Mount Beacon and Breakneck Ridge, making both these hikes ideal day trips for city dwellers.
The Devil’s Path
Trailhead Location: Prediger Road, Elka Park
Hike Length: 24 miles (approximately)
Total Ascent: 9,000+ feet
Time: 1-2 days
Intensity: Most Difficult
The notorious Devil’s Path trail in the Catskills is regularly listed as one of the toughest hikes in the United States. That’s because the trail is long and brutal, passing over 24 miles of deep Catskills wilderness. In doing so, it crosses seven mountains and some of the gnarliest terrain in the Northeast. But it’s also exceptionally beautiful and astonishingly scenic.
The Devil’s Path is a serious hiking challenge. You’ll scramble through ancient rock channels, slog through mud pits, and enjoy breathtaking boreal summits. In summer, there’s often no water along the trail. In the coldest months, some sections require full winter mountaineering gear.
Most hikers section-hike the range, tackling one or two mountains at a time. However, an increasing number of hardy types have through-hiked it in a single day, starting and finishing in the dark. The Devil’s Path remains one of the most challenging, respected and adored trails in the Hudson Valley.
The Catskill 9
Trailhead Location: Denning Road, Claryville
Hike Length: 23 miles
Total Ascent: 5,500 feet
Time: 12+ hours / overnight
Intensity: Super Intense
The Devil’s Path is the toughest blazed trail in the Catskills, but The Catskill 9 route ups the ante considerably. In addition to some of the most rugged mountain trails in the Catskill Park, this long loop includes a formidable off-trail section over six of the loneliest and toughest Catskill mountains—Lone, Rocky, Balsam Cap, Friday, Dink—before returning to rough, remote, beautiful trails. The Catskill 9 requires solid backcountry navigation skills, i.e. high competency with paper map and compass. It is, without doubt, the Catskills challenge.
The Santanoni Range
Trailhead Location: Santanoni Road, Newcomb
Hike Length: 16.8 miles
Total Ascent: 4,600 feet
Time: 10-12 hours
Intensity: Extremely Challenging
If you’re working on your Adirondack 46er list, you already know about (and possibly dread) the Santanoni Range loop—widely considered to be one of the most grueling day hikes in the Adirondack Park. It’s a long route and includes some of the steepest, most rugged trails in the High Peaks. There’s even an infamous bog to contend with. On the plus side, stunning wilderness views are on tap just below the summits of all three peaks: Couchsachraga, Panther Peak, and Santanoni Peak. This is a tough, steep hike with prolonged rock scrambles. Cell coverage is non-existent for much of the route so plan accordingly. Knee-high gaiters, trekking poles, and plenty of food and hydration are advised.
Outro
Exploring these challenging trails in the Hudson Valley isn’t solely about physical endurance—it’s about uncovering a deeper connection with the natural world around you. As you navigate these hikes, you’ll uncover not only the stunning beauty of our region, but also the joy and fulfillment of embracing a challenge. So, prepare your gear, set your sights on the trail, and experience the most demanding hikes the Hudson Valley has to offer.
Sean O’Dwyer hikes and photographs the Hudson Valley every week. He also produces mountain-hiking.com, a hyper-detailed trail guide resource for Hudson Valley hikers.
