4.8
(6)
115
riders
21
rides
Touring cycling around Fort Montgomery offers routes through the scenic Hudson Valley, characterized by the Hudson River and the surrounding Hudson Highlands. The terrain includes paved roads with varying elevation gains, from moderate climbs to more challenging ascents, particularly around Bear Mountain. Cyclists can experience views of the Hudson River, Bear Mountain Bridge, and natural features like Popolopen Creek. The region provides a mix of surfaces, with primarily paved routes and some unpaved segments.
Last updated: June 29, 2026
5.0
(1)
4
riders
47.7km
03:58
860m
860m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
15
riders
13.1km
01:03
340m
340m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(3)
20
riders
170km
10:21
1,450m
1,450m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
10
riders
76.3km
06:29
1,470m
1,470m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.0
(1)
16
riders
17.5km
01:08
150m
150m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Bear Mountain, located in the Hudson Highlands of southeastern New York, is one of the most notable landmarks on the Appalachian Trail in the state. The AT crosses directly over the summit, which stands at 1,305 feet, which is not especially high, but it is a historically and symbolically significant summit; it’s home to the oldest continuously maintained section of the Appalachian Trail, built in 1923, and features wide stone steps and paved walkways constructed by trail crews and the Civilian Conservation Corps. For many hikers, Bear Mountain is also the site of the lowest elevation point on the AT, near the Hudson River just before the climb. From the top, you get sweeping views of the Hudson Valley, and the surrounding Bear Mountain State Park includes a lake, picnic areas, the Trailside Museum and Zoo (which the AT technically passes through), and access to nearby Perkins Memorial Tower. It’s a popular day hike, so don’t be surprised to share the trail with weekend crowds, especially in fall.
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Bear Mountain peaks at just under 1,300 feet in elevation over a 4.5-mile stretch of picturesque paved road. Although it may seem small in comparison to some of the world’s renowned climbs, it makes up for this with stunning views of the Hudson Highlands.
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Nice view of the Tarrytown Reservoir. The trail runs very close to the water, so you have a wonderful, unobstructed view across the reservoir. The path is popular with cyclists, so make sure you move to the edge if you want to stop to enjoy the great vistas.
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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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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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Beautiful lake, at the eastern end there is a kayak rental in summer. A short boat trip loosens up the cycle tour and cools you down.
4
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Great views of Croton reservoir and the red bridge itself is worth a stop. That said watch out for stopped cyclist and pedestrians if you're biking through.
2
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Touring cycling around Fort Montgomery features a diverse landscape, primarily characterized by the scenic Hudson Valley, the Hudson River, and the surrounding Hudson Highlands. Routes are mostly paved, but some segments may be unpaved, offering a mix of surfaces. You can expect varying elevation gains, from moderate climbs suitable for most skill levels to more challenging ascents, particularly around Bear Mountain, which is known for its consistent 5% average grade. The region offers breathtaking views of the Hudson River and the majestic Bear Mountain Bridge.
There are over 20 touring cycling routes available around Fort Montgomery. These routes cater to various abilities, with options ranging from moderate to difficult, ensuring there's something for every cyclist looking to explore the scenic Hudson Valley.
Yes, Fort Montgomery offers touring cycling routes for various skill levels. While the majority of routes are classified as difficult (17 routes), there are also 4 moderate routes and 2 easy routes. For example, the View from Bear Mountain Summit – Perkins Memorial Tower loop from Bear Mountain State Park is a moderate option, providing panoramic views without extreme difficulty.
The routes around Fort Montgomery are rich in natural beauty and historical significance. You can expect sweeping views of the Hudson River and the Bear Mountain Bridge. Notable natural features include Popolopen Creek, Hessian Lake, and the Hudson Highlands. Historically, the area is home to the Fort Montgomery State Historic Site, a pivotal Revolutionary War location. You might also encounter highlights like the View of the Hudson River from Bear Mountain or the Hessian Lake.
Absolutely. Many routes in the Fort Montgomery area are celebrated for their stunning viewpoints. The View from Bear Mountain Summit – Perkins Memorial Tower loop from Bear Mountain State Park specifically leads to Perkins Memorial Tower, which offers panoramic views south across the Hudson, Harriman State Park, and the Appalachian Trail. Other highlights include the View of the Hudson Highlands from Bear Mountain and the View of the Hudson River and the Bear Mountain Bridge from Anthony's Nose.
The touring cycling routes in Fort Montgomery are highly rated by the komoot community, with an average score of 4.75 stars from over 6 reviews. Cyclists frequently praise the stunning natural scenery, particularly the views of the Hudson River and the challenging yet rewarding climbs around Bear Mountain. The diverse terrain, offering both paved and some unpaved sections, also contributes to a varied and engaging cycling experience.
Yes, Fort Montgomery offers several longer touring cycling routes for those seeking a more extensive ride. For instance, the Drum Hill – Creek Hill loop from Peekskill is a substantial 48.3-mile (77.7 km) trail, typically completed in about 6 hours 34 minutes. Another challenging option is the Tarrytown Reservoir – Whaley Lake loop from Peekskill, which spans 105.9 miles (170.4 km).
The Hudson Valley, including Fort Montgomery, is beautiful year-round, but touring cycling is particularly enjoyable during the spring, summer, and fall. Spring brings lush greenery, while autumn offers spectacular fall foliage. These seasons generally provide pleasant temperatures and clear conditions for riding. While some routes may be accessible in winter, conditions can be challenging due to snow and ice, especially on higher elevations like Bear Mountain.
Yes, many of the touring cycling routes around Fort Montgomery are designed as loops, allowing you to start and end at the same point. A popular example is the Candlewood Hill Loop, a 29.6-mile (47.7 km) trail that navigates the varied terrain of the Hudson Highlands. Another is the View from Bear Mountain Summit – Perkins Memorial Tower loop from Bear Mountain State Park.
Bear Mountain State Park, adjacent to Fort Montgomery, is a major hub for outdoor activities and offers parking facilities. For public transport, options might be limited directly to trailheads, but regional bus services or trains to nearby towns like Peekskill could provide access points, though further travel to specific starting points might be required. It's advisable to check local transport schedules and parking availability for your chosen route in advance.
While many routes in Fort Montgomery involve moderate to difficult elevation gains, Bear Mountain State Park offers a large play field and generally well-maintained roads and trails that can be suitable for families, depending on the specific path chosen. For easier, flatter sections, exploring areas around Hessian Lake within the park might be a good starting point for families.
Yes, the Fort Montgomery area and particularly Bear Mountain State Park offer amenities for cyclists. Bear Mountain State Park has shaded picnic groves and facilities. Nearby towns and villages in the Hudson Valley also provide cafes, pubs, and accommodation options where you can refuel and rest during or after your ride. It's always a good idea to plan your route and check for available services along the way.
While many touring cycling routes around Fort Montgomery are primarily paved, some segments may be unpaved, offering a mixed-surface experience for adventurous riders. For example, the Indian Brook Road - gravel – Sunken Mine Road loop from Peekskill explicitly mentions gravel in its name, indicating a route with unpaved sections.


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