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United States
New York
Orange County

Village of Highland Falls

The best walks and hikes around Village of Highland Falls

4.7

(227)

2,851

hikers

156

hikes

Hiking around Village of Highland Falls NY is set within the Hudson Highlands, a region characterized by steep, rocky hills and commanding views of the Hudson River. The area's trails navigate through dense woodlands and past water features like Popolopen Creek. Many routes are located within Bear Mountain State Park, offering a mix of terrain from riverside paths to ascents with significant elevation gain.

Best hiking trails around Village of Highland Falls

  • The most popular hiking route is Popolopen Gorge…

Last updated: April 27, 2026

6

hikers

#1.

Sugarloaf Hill and Osborne Loop

10.8km

03:12

310m

300m

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Moderate

1

hikers

2.55km

00:41

20m

60m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

6

hikers

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

25

hikers

9.91km

02:55

290m

290m

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Popular around Village of Highland Falls

Cycling around Village of Highland Falls

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Tips from the Community

mtm05005
July 20, 2023, Castle Rock Unique Area

Castle Rock Unique Area is a large estate that was owned by the president of the Illinois Central Railroad company as a summer home. Much of the land of the estate has since been donated to the Department of Environmental Conservation. The castle that was built on the property is still private property, so it is not open to the public.

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There are 2 trailheads to Antony's Nose: one northwest of Manitou Mountain, one southeast of it. Both have some parking but can be full in good weather. The shorter section can be easily completed in 30-45 minutes (each way).

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Frequently Asked Questions

Are there any easy, family-friendly hikes in the Highland Falls area?

Yes, the region offers several options suitable for families. The Brooks Pond & Popologen Gorge Trail loop is a great choice, offering a relatively flat 4.4-mile (7.1 km) path through forests and along the water. For an even more relaxed walk, the paved path around Hessian Lake in Bear Mountain State Park provides beautiful views of the surrounding mountains without any strenuous climbing.

Can I bring my dog on the trails around Highland Falls?

Many trails in the Hudson Highlands are dog-friendly, but policies can vary by park and dogs must typically be kept on a leash. Bear Mountain State Park and Hudson Highlands State Park Preserve generally permit dogs on trails. Always check the specific regulations for the park you plan to visit before you go and be prepared to clean up after your pet.

Are there any hikes with waterfalls near Highland Falls?

The Popolopen Gorge Trail loop follows Popolopen Creek, which features cascades and a natural waterfall with a plunge pool. The flow is most impressive after a period of rain. This trail offers a great opportunity to enjoy the sights and sounds of flowing water as part of your hike.

What's the difference between the Popolopen Torne and Popolopen Gorge trails?

The main difference is the terrain and objective. The Popolopen Torne loop is a challenging hike involving a steep, rocky scramble to a bald summit for panoramic views. In contrast, the Popolopen Gorge trail is a more moderate walk that stays low, following the creek through a wooded gorge, focusing on waterside scenery rather than high-elevation vistas.

Where can I park for hikes in Bear Mountain State Park?

Bear Mountain State Park has several large parking lots near Hessian Lake and the Bear Mountain Inn. These lots serve as the primary access for many popular trails, including those heading up Bear Mountain and into the Popolopen Gorge. A parking fee is typically charged, especially on weekends and during peak season. Arrive early as lots can fill up quickly.

How can I access the trails using public transport?

The Metro-North Railroad's Hudson Line is a great option. The Manitou station is located right next to the trail network, providing direct access to hikes in the Hudson Highlands. The Hiking loop from Manitou is one example of a route that starts directly from the station, making for a convenient car-free day trip.

What are the trail conditions like in the Hudson Highlands?

Expect varied and often rugged terrain. Trails frequently feature steep, rocky sections, significant elevation gain, and uneven footing. The paths are generally well-marked but can be challenging. Proper hiking footwear with good grip is essential. After rain, rocks and roots can become very slippery.

Are there any circular hiking routes available?

Yes, many of the most popular hikes in the area are loops, allowing you to experience a variety of scenery without backtracking. For a longer, moderately challenging loop, consider the Castle Rock Unique Area loop. It offers a diverse experience through Hudson Highlands State Park Preserve.

Can I hike at West Point?

Public access to the United States Military Academy at West Point for hiking is generally restricted. While you can see the academy's grounds from viewpoints like the summit of Popolopen Torne, the hiking trails on the military reservation itself are not open to the general public. For hiking, focus on the adjacent state parks like Bear Mountain and Hudson Highlands.

Are there any scenic viewpoints I can get to without a long hike?

Yes. The Perkins Memorial Drive in Bear Mountain State Park allows you to drive to the summit of Bear Mountain. From the parking area, it's a very short walk to the Perkins Memorial Tower, which offers spectacular 360-degree views of the Hudson Valley, the Bear Mountain Bridge, and on clear days, the New York City skyline.

What do other hikers think of the trails around Highland Falls?

The area is very highly regarded by the komoot community, with trails earning an average rating of 4.7 out of 5 stars. Hikers frequently praise the stunning panoramic views from the summits, the well-maintained trail networks, and the satisfying challenge of the rocky ascents.

How many hiking trails are there near Highland Falls?

There is an extensive network of trails to explore. On komoot, you can find over 130 different hiking routes around Highland Falls, ranging from easy lakeside walks to difficult mountain climbs, ensuring there's a trail for every skill level.

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