4.7
(6)
295
riders
45
rides
Road cycling around Cornwall-On-Hudson offers diverse terrain on the western shore of the Hudson River in Orange County, New York. The region is characterized by challenging climbs, scenic landscapes, and views of the Hudson Highlands. Road cycling routes here navigate through areas with significant elevation changes, providing options for various fitness levels.
Last updated: April 30, 2026
19
riders
35.6km
02:04
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
14
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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14
riders
13.8km
00:49
190m
190m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
8
riders
94.2km
04:08
730m
730m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
8
riders
34.6km
01:46
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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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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The road makes a loop around the summit of Bear Mountain with the Perkins Memorial Tower at its center. From the top you get sweeping views south across the Hudson, Harriman State Park, and the route taken by the Appalachian Trail.
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The Walkway Over the Hudson, also known as the Poughkeepsie Bridge, is a steel cantilever bridge spanning the Hudson River between Poughkeepsie and Highland. Originally it was built as a railroad bridge in 1889, then closed in 1974 due to fire damage and later reopened as a pedestrian walkway in 2009. It connects the Hudson Valley Rail Trail with the Dutchess Rail Trail and is part of the Empire State Trail. Stretching 6,768 feet, it was the world’s longest pedestrian footbridge until 2016. The bridge is free to access and welcomes cyclists as well as foot traffic.
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There are over 40 road cycling routes available around Cornwall-On-Hudson, catering to various skill levels. You'll find options ranging from easy loops to challenging climbs with significant elevation gain.
For experienced riders seeking a challenge, the region offers routes with substantial climbs and elevation. A notable option is the Highland Falls – Bear Mountain Climb loop from United States Military Academy, which features significant elevation gain and scenic views. The Storm King Highway (Route 218) is also renowned for its demanding climbs and spectacular cliffside views, offering an unforgettable ride.
Yes, Cornwall-On-Hudson offers easier road cycling routes suitable for beginners. For instance, the Fort Putnam – Highland Falls loop from United States Military Academy is an easy 8.6-mile trail with varied terrain, often completed in under an hour.
Many of the road cycling routes around Cornwall-On-Hudson are designed as loops, allowing you to start and end at the same point. Examples include the Fort Putnam – Long Pond loop from United States Military Academy and the Prospect Hill loop from Newburgh, providing convenient circular journeys.
Road cycling routes in this region offer diverse landscapes, including views of the Hudson River, Storm King Mountain, and Black Rock Forest. You might pass by natural monuments like Storm King Mountain itself, or enjoy panoramic vistas from Mount Beacon Park. The area is rich in natural beauty and cultural sites like the Storm King Art Center are also nearby.
While specific routes directly through the Storm King Art Center are not typically road cycling paths, many routes in the area offer views of the surrounding landscape that inspired the center. Black Rock Forest offers diverse cycling opportunities, though some trails may be unpaved. You can find routes that traverse the general vicinity, allowing you to experience the natural beauty of these areas.
The road conditions on popular routes vary. The Storm King Highway (Route 218) is known for its challenging climbs and hairpin turns, offering a thrilling ride with spectacular cliffside views. While generally well-maintained, cyclists should always exercise caution, especially on winding sections and descents. Many routes feature a mix of paved and unpaved surfaces, so checking route details beforehand is advisable.
The best time of year for road cycling in Cornwall-On-Hudson is typically spring, summer, and fall. These seasons offer pleasant temperatures and vibrant scenery, from blooming foliage to colorful autumn leaves. Summer can be warm, so early morning or late afternoon rides are often preferred. Winter cycling is possible but requires appropriate gear and caution due to potential ice or snow.
Accessing Cornwall-On-Hudson and its cycling routes via public transport is possible, though it may require some planning. Metro-North Railroad provides service to nearby towns like Beacon and Salisbury Mills–Cornwall, from which you might be able to cycle to route starting points or arrange local transport. Checking specific train schedules and bike policies is recommended.
Parking for road cycling trails in Cornwall-On-Hudson is generally available near popular starting points, especially around the United States Military Academy at West Point, which serves as a common access point for several routes. Local parks and designated trailheads may also offer parking facilities. Always check for specific parking regulations and availability before your ride.
While Cornwall-On-Hudson itself may have limited dedicated bike rental shops, nearby larger towns in the Hudson Valley often offer rental services. It's advisable to search for bike rental options in neighboring communities if you plan to rent a road bike for your trip.
The road cycling experience around Cornwall-On-Hudson is highly rated by the komoot community, with an average score of 4.6 stars from over 6 reviews. Cyclists often praise the diverse terrain, challenging climbs, and the stunning scenic views of the Hudson River and Highlands.
While many routes feature significant elevation, there are easier options that can be more suitable for families or those looking for a less strenuous ride. The Fort Putnam – Highland Falls loop from United States Military Academy is an example of an easier route with varied terrain. Always check the route's difficulty and elevation profile to ensure it matches your family's capabilities.


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