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.
Last updated: May 16, 2026
5.0
(1)
8
runners
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.
7
runners
8.56km
00:53
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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23
runners
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
12
runners
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
10
runners
7.21km
00:49
190m
190m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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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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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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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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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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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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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