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United States
New York
Orange County

Fort Montgomery

The best running trails around Fort Montgomery

4.5

(3)

253

runners

35

runs

Jogging routes around Fort Montgomery offer a blend of natural beauty and historical significance. The region is characterized by the scenic Hudson River, the rugged Popolopen Gorge, and the forested hills of Bear Mountain State Park. Joggers can experience diverse terrain, from riverside paths to more challenging trails through woodlands and past historical sites. The area provides panoramic views of the Hudson River and the surrounding landscape.

Best jogging routes around Fort Montgomery

  • The most popular jogging route is Bear…

Last updated: May 16, 2026

5.0

(1)

8

runners

#1.

Bear Mountain Loop

18.2km

02:35

700m

700m

This difficult 11.3-mile jogging loop in Bear Mountain State Park offers challenging terrain and panoramic Hudson River views.

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Hard

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Tips from the Community

MojoHamuki
June 9, 2025, William Brien Memorial Shelter

If doing the shorter loop know that the turn off is to loop to the other side of the lake is right after the shelter. If you continue on the yellow path past youll come to a red cross trail. This will take you oddly to the middle of the highway. Also protect yourself the woods are LOADED with ticks. My friend was brushing them off every few minutes and when I got threw and we hit up the meal after, I found them crawling all over me. We mostly walked, never sat down anywhere and barely stood still.

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Jamie S.
February 14, 2024, Highland Falls

Highland Falls, situated in Orange County, New York, is a quaint village neighboring the renowned United States Military Academy at West Point. With a population of around 3,900, the village boasts a rich history intertwined with the academy's legacy. Its scenic location along the Hudson River and proximity to the Hudson Highlands State Park offer residents and visitors ample opportunities for outdoor recreation. With plenty of local shops, restaurants, and annual events, Highland Falls is a great spot for residents and visitors alike to relax after a long ride or hike.

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Jamie S.
February 14, 2024, Fort Putnam

Fort Putnam, named after Revolutionary War General Israel Putnam, is a historic military fortification located in West Point, New York. Constructed between 1778 and 1780 by the Continental Army during the American Revolutionary War, it played a significant role in defending the Hudson River Valley from British forces. Situated atop a strategic hill overlooking the Hudson River, Fort Putnam served as a key stronghold and provided a vantage point for monitoring enemy movements. The fortification features stone walls, earthworks, and cannons, embodying the military architecture of the period. Today, Fort Putnam is part of the United States Military Academy at West Point and is open to visitors, offering insight into America's military history.

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Scott
January 18, 2024, Highland Falls

Highland Falls, once Buttermilk Falls, transformed into a village in Orange County. Officially incorporated in 1906, it boasts a population of 3,684 as of 2020. Recognized for its suburban allure, the town is esteemed as one of the best places to live in New York, featuring numerous bars, restaurants, and coffee shops.

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Scott
January 18, 2024, Fort Putnam

Fort Putnam, a Revolutionary War garrison in West Point, New York, offers spectacular views. The museum eloquently recounts the area's significant role during the Revolutionary War, creating a compelling historical narrative.

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oliviakellis
September 14, 2023, Creek Bridge

When you reach the creek, you'll see a small bridge, but the waterway is narrow enough to cross via the rocks in low water seasons. Using the stones may be safer than going across the aging bridge.

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At 1,348 feet, South Stockbridge Mountain will reward you with beautiful views, especially in the winter when the trees are bare. There's plenty of space to sit and enjoy the views.

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Felix
October 31, 2022, Hessian Lake

Nice small lake in Bear mountain state park. In the summer you can rent a paddle boat and fishing is allowed in season

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Frequently Asked Questions

How many running routes are available around Fort Montgomery?

Fort Montgomery offers a wide selection of running routes, with over 45 trails available for exploration. These routes cater to various skill levels, from moderate paths to more challenging trails through woodlands and past historical sites.

What kind of terrain can I expect on the jogging trails in Fort Montgomery?

The running trails around Fort Montgomery feature diverse terrain. You can find everything from paved paths to more challenging, uneven surfaces with rocks and roots. Routes vary in difficulty, including easy, intermediate with small hills, and difficult with steep sections, often providing stunning views of the Hudson River and Popolopen Gorge.

Are there any easy or beginner-friendly running routes in the Fort Montgomery area?

Yes, Fort Montgomery offers options for all skill levels. There are 5 easy routes available, perfect for beginners or those looking for a more relaxed run. While specific names aren't highlighted here, you can find suitable paths within the broader network that avoid significant obstacles and steep climbs.

What are some of the more challenging running routes around Fort Montgomery?

For experienced runners seeking a challenge, Fort Montgomery has 21 difficult routes. One such demanding option is the Doodletown Pond and Dam loop from Bear Mountain State Park, which covers over 12 miles (20 km) with significant elevation changes, offering a rigorous workout amidst scenic landscapes.

Are there any running routes that offer historical sights or landmarks?

Absolutely! Fort Montgomery is rich in history. Many routes pass by significant historical sites. For instance, the Fort Putnam loop from United States Military Academy provides historical context and views around Fort Putnam. You can also explore trails within the Fort Montgomery State Historic Site itself, which feature archeological remains and a museum. The Cornish Estate Ruins (North Gate) are another fascinating historical highlight you might encounter on nearby trails.

Can I find running routes with scenic views of the Hudson River or other natural features?

Many running routes in Fort Montgomery boast breathtaking views. The region is defined by the Hudson River, the dramatic Popolopen Gorge, and the forested hills of Bear Mountain State Park. From various vantage points, including those within the Fort Montgomery State Historic Site, you can enjoy panoramic vistas of the Hudson River and the iconic Bear Mountain Bridge. The View of the Hudson River from Bear Mountain is a particularly popular highlight.

Are there any loop running trails in Fort Montgomery?

Yes, loop trails are a popular option for runners in Fort Montgomery. A notable example is the Bear Mountain Bridge – Hessian Lake loop from United States Military Academy, which is a longer route leading through forested areas and past Hessian Lake. Many other trails in the area are designed as loops, allowing you to start and finish at the same point.

What do other runners say about the trails in Fort Montgomery?

The running routes in Fort Montgomery are highly regarded by the komoot community, holding an average rating of 5.0 stars from more than 1 review. Over 370 runners have used komoot to explore the varied terrain, often praising the stunning natural beauty, the historical significance of the sites, and the diverse range of trails available for all abilities.

Are there any running routes that pass by lakes or other water features?

Yes, the region features several beautiful water bodies. The Popolopen Gorge, with Popolopen Creek running through it, is a prominent natural feature that many trails follow or overlook. Additionally, the Bear Mountain Bridge – Hessian Lake loop specifically takes you past Hessian Lake, offering picturesque waterside running.

Is there parking available near the running trails in Fort Montgomery?

Parking is generally available at key access points for trails, particularly within Bear Mountain State Park and near the Fort Montgomery State Historic Site. It's advisable to check specific trailheads or park websites for detailed parking information and any potential fees or restrictions.

What is the best time of year to go running in Fort Montgomery?

Fort Montgomery offers excellent running opportunities throughout much of the year. Spring and fall provide pleasant temperatures and vibrant foliage, making them particularly popular. Summer can be warm, but shaded trails offer relief. Winter running is possible, but conditions may vary, with some trails potentially becoming icy or snowy, so checking local conditions is recommended.

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