4.7
(3)
91
riders
5
rides
Road cycling around Washingtonville, New York, offers routes through the rolling hills of Orange County in the lower Hudson Valley. The region features scenic landscapes with accessible trails, including paved greenways that wind past wetlands and open fields. The terrain is characterized by small-town charm, rivers, farms, and distant mountain views, providing a varied backdrop for road cyclists.
Last updated: July 11, 2026
4.7
(3)
74
riders
93.2km
04:35
1,070m
1,070m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
4
riders
30.7km
01:20
230m
230m
The Orange Heritage Trail loop from Monroe offers a delightful road cycling experience, tracing a former rail bed through a varied landscape of woodlands, rolling meadows, and farmland. You'll glide…

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7
riders
25.4km
01:19
400m
400m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
56.5km
02:36
390m
390m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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The Orange Heritage Trail is an almost 20-mile long rail trail that runs from Middletown to Harriman. It is paved and traffic-free. This section is used by the Long Path to take you from Monroe to Chester.
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The windiest piece of rail trail I've ever seen
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This longer section of the Walden-Wallkill Rail Trail is completely paved and is pretty flat. Since it follows an old train line, it technically climbs slightly uphill in one direction and is completely downhill when traveling in the other direction.
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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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The Shawangunk Grasslands National Wildlife Refuge covers an area of 597 acres. It was initiated to support migratory birds and wintering raptors. It has great views of the stunning Shawangunk Ridge. It is a beautiful area to cycle around.
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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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There are 5 road cycling routes around Washingtonville featured in this guide, offering a range of experiences from easy, paved greenways to more challenging rides with significant elevation gain. The komoot community has explored over 90 routes in the area, indicating a broader network of options.
The best time for road cycling in Washingtonville, located in the lower Hudson Valley, is generally during the spring, summer, and fall months. These seasons offer pleasant weather for exploring the scenic landscapes, rolling hills, and farmlands. Winter conditions can be challenging due to cold temperatures and potential snow or ice.
Yes, the region features accessible paved greenways. A great option is the Orange Heritage Trail loop from Village of Monroe. This easy 19.1-mile (30.7 km) path follows a paved greenway, winding past wetlands and open landscapes, making it ideal for a relaxed ride.
Road cycling around Washingtonville is characterized by rolling hills, scenic farmlands, and accessible paved greenways. While some routes, like the Heritage Trail, are relatively flat, others, such as the Bear Mountain Bridge – View of Storm King Mountain loop from Salisbury Mills-Cornwall, feature significant elevation gain, providing options for various ability levels.
Many routes offer scenic views of the Orange County landscape. The Bear Mountain Bridge – View of Storm King Mountain loop from Salisbury Mills-Cornwall provides stunning views of Storm King Mountain. Additionally, the Orange Heritage Trail itself is a landmark, offering picturesque views of wetlands, wildflowers, and grazing horses along its path.
Parking is generally available at various access points for popular trails like the Orange Heritage Trail. For specific routes, it's advisable to check the individual route details on komoot, as starting points often have designated parking areas.
The road cycling routes in Washingtonville are highly rated by the komoot community, with an average score of 4.6 stars from over 3 reviews. Cyclists often praise the varied terrain, from easy paved paths to challenging climbs, and the scenic beauty of the rolling hills, farmlands, and distant mountain views.
Yes, several routes are designed as loops, allowing you to start and end at the same point. Examples include the Orange Heritage Trail loop from Village of Monroe and the Bear Mountain Bridge – View of Storm King Mountain loop from Salisbury Mills-Cornwall, providing convenient options for your ride.
While specific cafe stops are not detailed for every route, Washingtonville and the surrounding small towns in Orange County offer local cafes, pubs, and restaurants. The Deli Breakfast & Lunch loop from New York Stewart International Airport even suggests a route with dining in mind, indicating that such amenities are accessible.
Yes, experienced riders can find challenging routes with significant elevation. The Bear Mountain Bridge – View of Storm King Mountain loop from Salisbury Mills-Cornwall is a difficult 57.3-mile (92.2 km) trail featuring over 1,000 meters of elevation gain, offering a demanding ride through the region's more mountainous terrain.
The region is rich in natural beauty. The Orange Heritage Trail passes through wetlands and open fields. Nearby, you can find the Stewart State Forest, which, while primarily for hiking and mountain biking, features diverse wildlife and natural landscapes. The Maybrook Reservoir and Wilkens Pond are also local natural attractions.
Many routes in Orange County connect or pass through charming small towns, offering a glimpse into the region's local character. For instance, the Orange Heritage Trail loop starts from the Village of Monroe, and other routes often traverse the picturesque countryside between communities.


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