6 Winter Wonderland Hikes To Crush in the Hudson Valley | Outdoors | Hudson Valley | Chronogram Magazine

It’s the dead of winter which means that, once again, cabin fever is upon us: shorter days, earlier nightfalls, fuzzier focus, disrupted sleep, unquenchable food cravings, crankiness—the mid-winter blues. Winter in New York is tough. But, especially in these darkest months, it’s crucial for New Yorkers to get outside. The Hudson Valley is crammed with some of the best hiking trails in the nation—and, luckily, we have winter wonderland terrain to match every skill level. Get yourself outside. Like Camus, you may find that within you, even in the depths of winter, lies an invincible summer.

Winter Hiking Tips

Winter hikes do require more gear and more planning than warm weather hikes. At the very least, on all but the flattest trails, you’ll need appropriate traction. (Yaktrax are great in suburban settings but they won’t cut it in the hills; the Catskills and Gunks are littered with broken scraps of Yaktrax.) Trail-grade traction opens up an incredible world of winter hiking. For winter mountain hikes, grab a pair of microspikes (AKA “trail crampons”) from Hillsound or Kahtoola. Appropriate layering is crucial too, and not only to protect yourself from the elements. Sweating on a hike in winter can be dangerous and, with all the extra exertion, you may need to unzip and delayer to modulate your temperature down. Pack extra snacks and hydration; you’ll definitely burn more calories. Know what time sunset is at. Keep your phone next to your body so the battery doesn’t die in the cold. Always pack a headlamp; your phone’s weak light is useless in the woods. To learn more about winter hiking, read How to Winter Hike: The Essential Roundup.

Ready to hit the trail? Grab a friend or two and organize a winter-blues-beating/life-affirming winter hike. The following hikes are all free, including the parking. Leashed dogs are welcome. Just remember: you and your pooch should always Hike Smart and follow Leave No Trace principles.

Hudson Valley & Catskills Winter Hikes

Windham High Peak from Route 23

click to enlarge 6 Winter Wonderland Hikes To Crush in the Hudson Valley
View of the Blackhead Range from the summit of Windham High Peak

Trailhead Location: Elm Ridge Parking Area on Route 23 between Windham and East Windham
Hike Length: 7.5 miles (12km) out-and-back
Total Ascent: 1,800 feet (550m)
Intensity: Moderate

One of the easiest of the Catskills High Peaks to hike at any time of year, Windham High Peak has it all: incredible trails that wind through stunning hemlock woods and Norway spruce plantations, and a summit that offers three amazing lookouts with views to the south, north, and east. There are two main trailheads to choose from. From the south, you can start at the Peck Road trailhead near Maplecrest. From the north, the large lot on Route 23 at Cross Road is a great place to begin—the initial walk in, over multiple wooden boardwalks, is easy and beautiful. There are no technical challenges on this hike: no stream crossings or rock scrambles, just solid hillwalking. Open year-round.

Huckleberry Point

click to enlarge 6 Winter Wonderland Hikes To Crush in the Hudson Valley
Plattekill, Overlook & Indian Head mountains seen at sunset across Platte Clove

Trailhead Location: Huckleberry Point Trailhead on Platte Clove Road
Hike Length: 5 miles (8km) out-and-back
Total Ascent: 975 feet (300m)
Intensity: Moderate

Huckleberry Point is one of the most dramatically scenic locations in the Catskills, and this hike is short enough that you can easily get it done on the shortest of winter days. From the busy lot on Steenburgh Road in Platte Clove, follow the blue blazes uphill via an old woods road. (The blazing on the trail is sometimes less than adequate and inexperienced hikers have had issues here, so having navigation on your phone with an app like AllTrails is advised.) At the second major junction, switch to the yellow spur trail which will take you out to a stunning rock ledge. Enjoy epic views into the clove below and east toward the Hudson Valley. Note: In winter, the eastern side of Platte Clove Road is closed so you’ll need to come down to Platte Clove from Tannersville/Route 23A.

Stissing Mountain Fire Tower

click to enlarge 6 Winter Wonderland Hikes To Crush in the Hudson Valley
Stissing & Thompson ponds seen from Stissing Fire Tower’s open cabin

Trailhead Location: Stissing Mountain Fire Tower Parking Area in Pine Plains, NY
Hike Length: 2 miles (3.2 km) loop
Total Ascent: 800 feet (245m)
Intensity: Moderate

The lower portion of the well-worn trail up Stissing Mountain has recently been rerouted to make it more sustainable, and a little easier on the legs. Still, Stissing is a bit of a huffer, with some steep trail sections, so think of this as a short, sharp work-out. And bring your best head for heights. Views from the exceptionally tall fire tower include Thompson and Stissing ponds directly below, a long line of ancient Taconics to the east, and fistfuls of Catskills High Peaks to the west.

Storm King Mountain & Butter Hill from Stowell

click to enlarge 6 Winter Wonderland Hikes To Crush in the Hudson Valley
At Storm King, looking south down the Hudson River

Trailhead Location: Esty and Hellie Stowell Trailhead, 42 Bayview Avenue, Cornwall-On-Hudson, NY 12520
Hike Length: 5.4 miles (8.7km) loop
Total Ascent: 1700 feet (520m)
Intensity: Strenuous

This route begins at the Esty & Hellie Stowell trailhead in Cornwall-on-Hudson. This trail is quieter than the trails that start further south along Route 9W. There are excellent views on the way up. But the best views are all below the summit. Look south across the Hudson River to Breakneck Ridge and Bull Hill. On the way out, look north to the Newburgh-Beacon Bridge, Mount Beacon, the Gunks, and the Catskills. From Butter Hill, Schunemunk Mountain is plainly visible.

Anthony’s Nose

click to enlarge 6 Winter Wonderland Hikes To Crush in the Hudson Valley
At Anthony's Nose, looking west across the Hudson River to Bear Mountain

Trailhead Location: Route 9D roadside parking in Garrison, NY
Hike Length: 1.9 miles (3 km) out-and-back
Total Ascent: 675 feet (205m)
Intensity: Moderate

Ever-popular due to its incredible Hudson River view, Anthony’s Nose is a short, steep hike, easily accessible from New York City and New Jersey. Park your car north of Bear Mountain Bridge on Route 9D or, if you’d prefer a similar but slightly longer hike of 2.5 miles, park south of the bridge at the small hairpin lot on Route 6. From either trailhead, make your way uphill to the edge of the rocky promontory to enjoy stunning views across to Bear Mountain, as well as up and down the mighty Hudson River.


Trailhead Location: Woodland Valley Campground in Phoenicia, NY
Hike Length: 7 miles (11.25 km) loop
Total Ascent: 2700 feet (825m)
Intensity: Strenuous / Challenging

By far, the most challenging and rewarding day on this list is the winter hike from Woodland Valley to the summit of Wittenberg Mountain in the heart of the Catskills. The trail is immediately steep, then provides something of an intensity break before the very steep final climb to the summit’s open ledge. Routinely described as the finest view in the Catskills, the 180-degree panorama takes in Samuels Point stretching down to the Ashokan Reservoir, as well as Ashokan High Point. To the left, in the distance, an array of Devil’s Path mountains. To the right, Friday Mountain and Balsam Cap are visible. For experienced mountain hikers, this is one of the grandest of destinations in the Catskills.

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.

About The Author

Sean O'Dwyer

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.
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