4.7
(37)
520
riders
43
rides
Touring cycling routes in Orange County, New York, offer a variety of experiences across its diverse landscape. The region features a mix of rail trails, lake loops, and routes through towns and villages. These trails provide options for different skill levels, from easy rides to more challenging routes with significant elevation gain.
Last updated: July 21, 2026
91.5km
05:41
580m
580m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.6
(5)
26
riders
25.9km
01:32
140m
140m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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4.8
(10)
47
riders
48.7km
02:54
240m
240m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
38
riders
28.0km
02:50
470m
470m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
23
riders
16.4km
01:44
320m
320m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
17
riders
15.4km
00:54
80m
80m
Easy bike ride. Great for any fitness level. 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.
16
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
12
riders
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
12
riders
16.1km
01:37
250m
250m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Orange County
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Cycling around Village of Highland Falls
Cycling around Town of Highlands
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Lovely Trail from end to end. Middletown NY to Herriman NY
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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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Crane Park (sometimes referred to as Millpond Park) is home to a couple small ponds, a gazebo, paved walking paths, and lots of open green space. There is easy access over to the Orange Heritage Trail from the park and a couple different parking areas that you can utilize.
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The Orange Heritage Trail stretches a total of 19.5 miles from Middletown to Harriman, New York. The path is entirely paved and is super popular among runners, walkers, and cyclists. There are a bunch of different trailheads and parking areas, so you can start your walk from a number of spots and make it as long as you want.
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Point Peter serves as a pretty sweet lookout over the Delaware River. Elks-Brox Memorial Park features a handful of trails, some tougher and some easier. Whichever trail you use to climb to the top, this viewpoint is well worth the effort.
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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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Shepherd Lake is a beautiful lake in a very scenic setting. There is car parking here, and nearby is some greenspace with benches and some trees, not that many, but some, so you can take in the shade on a hot day if you get the right spot. Nearby is also a beach. It is a nice scenic place to take a break on a tour, or better yet, a great family bike ride location.
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Once the location of the Erie Railroad's Main Line, this is now a paved multi-use trail that runs 19.5 miles in total.
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Orange County offers a wide variety of touring cycling routes, with over 30 options available. These routes cater to different skill levels, including easy, moderate, and difficult rides.
Orange County, New York, features diverse landscapes for touring cyclists. You'll find routes that follow historic rail beds, loop around scenic lakes, and connect charming towns and villages, offering a mix of natural beauty and local culture.
Yes, Orange County has several easy touring cycling routes. A great option is the Chester Erie Depot Museum – Orange Heritage Trail loop from Village of Goshen, which is 16.1 miles long and provides a pleasant ride through the local area. Another easy choice is the Echo Lake loop from City of Middletown, spanning 13.8 miles.
For those seeking a challenge, the Wallkill Valley Rail Trail is a difficult 56.9-mile route following a historic rail bed. Another demanding option is the Highland Falls – Long Pond loop from Salisbury Mills-Cornwall, which covers 52 miles with significant elevation gain.
Many routes in Orange County are designed as loops, perfect for starting and ending in the same location. Examples include the easy Chester Erie Depot Museum – Orange Heritage Trail loop from Village of Goshen and the moderate Huguenot Hill loop from City of Port Jervis.
The touring cycling routes in Orange County are highly regarded by the komoot community, holding an average rating of 4.5 stars from over 30 reviews. Cyclists often praise the varied terrain and the well-maintained rail trails.
Yes, for long-distance touring, the Wallkill Valley Rail Trail is an excellent choice, stretching 56.9 miles. Another substantial route is the Highland Falls – Long Pond loop from Salisbury Mills-Cornwall, which is 52 miles long.
While cycling in Orange County, you can explore various natural and historical points of interest. Nearby attractions include several mountain peaks like Storm King Mountain and viewpoints such as the View of the Hudson River from Bear Mountain. There are also huts and shelters like Bald Rocks Shelter for those exploring longer routes.
Yes, Orange County features routes that incorporate beautiful lake scenery. The Lake Askoti – Lake Tiorati loop from Tuxedo is a 28.2-mile difficult route that takes you around these picturesque lakes. The Echo Lake loop from City of Middletown also provides pleasant water views.
Absolutely. Many touring cycling routes in Orange County are designed to connect local villages and towns, allowing you to experience the region's charm. The Orange Heritage Trail – Chester Erie Depot Museum loop from Harriman is a 30.2-mile route that leads through varied terrain, often connecting different communities.
Orange County offers enjoyable cycling experiences throughout much of the year. Spring and fall typically provide pleasant temperatures and beautiful scenery, with vibrant foliage in autumn. Summer is also popular, though it can be warmer, while winter cycling depends on snow and ice conditions.


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