5.0
(1)
36
riders
5
rides
Touring cycling around New Windsor, New York, offers diverse landscapes within the Hudson Valley. The region features rugged mountains, rolling hills, and extensive trail networks along the Hudson River. Terrain includes paved sections, crushed-stone paths, and challenging gravel roads with significant elevation changes. Natural features like Black Rock Forest and Schunemunk Mountain State Park provide varied cycling environments.
Last updated: May 17, 2026
10
riders
39.1km
03:15
800m
800m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
41.0km
03:24
670m
670m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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3
riders
27.1km
01:47
360m
370m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
2
riders
25.3km
01:35
230m
230m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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As a decent this was awesome! Right at the bottom of the first downhill you have some loose sand so be cautious. Right after that is a beautiful pond you loop right around, then another excellent downhill.
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Surprise climbs right after corners keep you on your toes. One particular steep climb (headed north just before Travis Corners Rd) makes for a rewarding summit. The decent headed towards the Bird and Bottle Inn was awesome!
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Very smooth gravel. Could even get out of saddle for some sections of the climb without losing traction
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There are over 8 touring cycling routes around New Windsor, offering a variety of experiences for different skill levels. The komoot community has explored these routes over 35 times.
The New Windsor area offers diverse terrain for touring cyclists. You'll find a mix of paved sections, crushed-stone paths, and challenging gravel roads, particularly in areas like Black Rock Forest. Routes often feature significant elevation changes, providing both scenic views and a good workout.
While many routes in the area are rated difficult, there are at least 2 moderate touring cycling routes available. These routes offer a less strenuous experience while still allowing you to enjoy the scenic Hudson Valley. One such route is Mount Beacon Park loop from Glenham, which covers 20.4 miles (32.8 km).
Touring cycling routes around New Windsor offer stunning natural features and viewpoints. You can encounter majestic summits like Storm King Mountain and Mount Beacon Park, serene lakes such as Beacon Reservoir, and even a beautiful Brook Falls. The region is known for its dramatic Hudson Valley scenery.
Yes, the Hudson Valley is rich in history. While cycling, you might pass by or near sites like the Ruins of the Mount Beacon Incline Railway Powerhouse or the Cornish Estate Ruins (North Gate). The broader region also features the New Windsor Cantonment State Historic Site and the National Purple Heart Hall of Honor, offering glimpses into Revolutionary War history.
The Hudson River Valley Greenway is a significant draw for touring cyclists in the region. It's part of the larger Empire State Trail, offering an extensive multi-use trail with scenic views along the Hudson River. This greenway provides continuous routes, often connecting charming river towns and allowing access to cultural sites, historic landmarks, and parks. You can find more information about the land trail sections on the Hudson River Valley Greenway website.
While specific family-friendly routes are not detailed in the current selection, the Hudson River Valley Greenway often includes sections suitable for families, with paved or crushed-stone paths. It's advisable to check individual route descriptions for terrain and difficulty to ensure they meet your family's needs.
The Hudson Valley, including New Windsor, is particularly beautiful for cycling in the spring and fall. Spring brings lush greenery and blooming flowers, while fall offers spectacular foliage. Summer can also be enjoyable, but it's wise to start earlier in the day to avoid the midday heat. Winters can be challenging due to snow and ice.
Yes, several circular touring cycling routes are available. For example, the challenging Indian Brook Road - gravel – Sunken Mine Road loop from Cold Spring is a 24.3-mile (39.1 km) route, and the Sunken Mine Road loop from Cold Spring is a longer 40.2-mile (64.7 km) option, both offering a complete loop experience.
The touring cycling routes around New Windsor are highly rated by the komoot community, with an average score of 3.0 stars from over 2 reviews. Cyclists often praise the scenic river views, challenging mountain roads, and the extensive multi-use trails that define the area's cycling experience.
Rules regarding dogs vary by specific trail and park. While some multi-use trails may permit leashed dogs, it's essential to check the regulations for each individual route or park you plan to visit. For instance, Black Rock Forest allows bicycles on forest roads but specific dog rules should be verified.
Parking availability depends on the specific trailhead or access point. Many state parks and trailheads along the Hudson River Valley Greenway offer designated parking areas. It's recommended to check the starting point of your chosen route for specific parking information.
Public transport options to access trails near New Windsor can be limited. However, some sections of the Hudson River Valley Greenway are accessible from towns with train stations (e.g., Metro-North Railroad stops in the Hudson Valley), which might allow bikes. It's best to research specific public transport routes and their bike policies in advance.


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