🌲 Five Must-Do Winter Hikes in New York (From Easy Waterfalls to Adirondack Peaks)

Amber in New England | November 2025

Winter hiking in New York is wildly underrated. New York offers some incredible winter hiking opportunities, and these five trails are must-dos for scenic adventure.

❄️ Five Must-Do Winter Hikes in New York

A. Bear Den Mountain (Adirondacks)

Quick Facts	Details
Location	Wilmington, Adirondack Mountains (Near Whiteface Mountain)
Distance	3.4 miles Round Trip
Difficulty	Moderate (Steady Uphill Climb)
Key Attraction	Stunning views of Whiteface Mountain and the Sentinel Range.

Hiking Bear Den Mountain is a great way to experience the Adirondack beauty without the intense commitment of an Olympic-region high peak. The trail is well-maintained and offers stunning views of the surrounding area, including Whiteface Mountain.

The trailhead is located at the Bear Den lot within the Whiteface Mountain Ski Area off of Route 86. Be mindful of this location: you will share the initial section of trail with cross-country skiers, so always stay aware of your surroundings! The climb is mostly uphill, but at just 1.6 miles to the top, it’s a rewarding half-day effort.

B. Kaaterskill Falls (Catskills)

Quick Facts	Details
Location	Haines Falls, Eastern Catskill Mountains
Distance	2.0 miles Round Trip (to the base)
Difficulty	Moderate / Challenging (Steep, Icy Staircase)
Key Attraction	One of New York's highest waterfalls, often frozen solid in winter.

Kaaterskill Falls is a stunning, two-stage waterfall with an overall drop of 260 feet. In the winter, this is one of the most magnificent sights in the state, with massive ice columns forming.

The hike to the base is about two miles round trip, starting easy and switching to slightly moderate before the steep incline and long winding staircase leading to the base.

Be warned: This trail is extremely popular and, in winter, the stone steps are often coated in a sheet of deadly ice.

⚠️ Critical Safety Alert: Traction is absolutely mandatory here. Also, stay well clear of the base of the falls to avoid falling ice (verglas) and do not attempt to climb on the frozen falls.

• Parking: Parking along Route 23A is strictly prohibited and vehicles will be ticketed or towed. Park legally at designated DEC lots (like Laurel House Road) or at the Mountain Top Historical Society and follow the marked trails.

C. Dover Stone Church (Hudson Valley)

Quick Facts	Details
Location	Dover Plains, Hudson Valley
Distance	2.5 miles Round Trip
Difficulty	Easy (Mostly Flat)
Key Attraction	A historic, cathedral-like cave with a 30-foot waterfall inside.

If you're looking for a hike that feels truly magical, head to Dover Plains. The hike to the cavern is an easy one on a relatively flat and well-defined trail. The cave entrance is a Gothic archway, and when we went, the snow was perfectly placed and icicles covered the stones. It was the most magical place I have ever seen.

• Parking Tip: The official site has no on-site parking. We successfully parked in the Dover Elementary School parking lot across the street (on a weekend) and had to walk up a gravel driveway that can look private. Be respectful, do not block the driveway, and look for the official sign.

• Safety Alert: The rivers edge and the rocks inside the cavern were extremely icy when we visited. Spikes are essential here for safety.

D. Potash Mountain (Adirondacks)

Quick Facts	Details
Location	Minerva, Adirondack Mountains
Distance	4.5 miles Round Trip
Difficulty	Moderately Difficult (Steady Climb, Rocky Sections)
Key Attraction	Breathtaking 360-degree views of the High Peaks region from the summit.

This Adirondack hike is about 4.5 miles round trip and is considered moderately difficult due to its length and terrain. The trail is well-marked and is a steady, enjoyable climb.

The sections closer to the summit are very rocky, and those rocks will often hold onto ice, even when other parts of the trail are clear. Once you reach the summit of Potash Mountain, you'll be treated to a breathtaking 360-degree view of the mountains. The perfect reward for the uphill climb.

E. Awosting Falls (Shawangunks)

Quick Facts	Details
Location	Minnewaska State Park Preserve, New Paltz
Distance	2.5 miles Round Trip
Difficulty	Easy (Wide Carriageway Trail)
Key Attraction	A beautiful cascade with stunning, giant blue icicles in deep winter.

Awosting Falls is a beautiful waterfall located in the popular Minnewaska State Park Preserve in the Shawangunk Mountains. The trail is an easy 2.5 miles round-trip. You can find the trailhead at the Upper Awosting Parking Area.

This hike begins with a gradual climb on a wide, carriage-style path. After about a mile, the trail reaches the base of the falls, where visitors can take in the breathtaking views of the cascading water and the bluest, largest icicles I have ever seen hanging from the cliffs. If you are brave enough to get an up-close peek, watch your step and your head! This is another excellent spot to extend your day by exploring the rest of the Minnewaska State Park trails.

If you prefer shorter hikes with big payoffs closer to home, Northwest Connecticut has plenty of options year-round.

Key Safety Note: The Gear You Cannot Skip

Before diving into these trails, a crucial reminder: Winter hiking in New York requires traction. Ice is common, especially around waterfalls and at higher elevations.

• Mandatory Gear Check: Every hike on this list requires you to pack micro-spikes or crampons. For a full breakdown on what to buy, subscribe to my e-mail list for my upcoming guide: Microspikes vs. Crampons: Which Winter Traction is Right for Your Hike?

• Safety Check: Always review my core advice before heading out: 5 Essential Winter Hiking Tips for New England.

Winter Hiking Safety Checklist

Winter hiking is a great way to enjoy the outdoors, but it requires preparation. Always follow this quick checklist:

• Tell Someone Your Plan: Communicate your exact route, parking location, and expected return time.

• Layer Correctly: Wear waterproof layers over insulating mid-layers and a wicking base layer.

• Pack Essentials: Bring a map and compass, a first aid kit, and extra food and water (insulate your water bottle!).

• Monitor Conditions: Be aware of the weather and terrain conditions so you can be prepared for any changes.

If you’ve only hiked New York in summer, winter will completely change how you see these trails.