4.7
(33)
809
riders
77
rides
Road cycling around Highland features routes that traverse river valleys and converted rail trails, offering a mix of flat sections and gentle ascents. The terrain is characterized by the Hudson River's scenic banks and the surrounding rolling hills, providing varied landscapes for cyclists. Many routes utilize established paths like the Dutchess Rail Trail, connecting communities and natural areas.
Last updated: May 5, 2026
5.0
(1)
42
riders
119km
05:54
1,260m
1,260m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
17
riders
107km
05:24
1,110m
1,110m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

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9
riders
67.6km
03:17
590m
590m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
7
riders
95.6km
05:19
1,500m
1,500m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
5
riders
133km
06:38
1,430m
1,430m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
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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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The Dutchess Rail Trail is a 13 mile traffic free path. It is built on an abandoned railway line. The trail runs from Hopewell Junction to the Walkway Over the Hudson in the City of Poughkeepsie
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Minnewaska State Park Preserve in New York enchants with its dramatic cliffs, pristine lakes, and lush forests. Visitors explore diverse trails, waterfalls, and the serene beauty of the Shawangunk Mountains.
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Lake Minnewaska is one of the sky lakes located on the Shawangunk Mountain ridge. It is a relatively small lake, and the surrounding trail is just under 2 miles in length. This trail can get quite busy with both walkers and cyclists, so be respectful of other trail users.
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There are over 70 road cycling routes in Highland, offering a wide range of options for different skill levels. The komoot community has explored these routes over 1000 times, with an average rating of 4.75 stars.
Road cycling in Highland features routes that traverse river valleys and converted rail trails, offering a mix of flat sections and gentle ascents. You'll experience the scenic banks of the Hudson River and surrounding rolling hills, providing varied landscapes.
Yes, Highland offers a good selection of easy road cycling routes. For instance, the 1889 Rail Bed Trail loop from Highland Park & Ride is an easy option, covering about 24 miles (38.9 km) with minimal elevation gain, ideal for a relaxed ride.
Many routes in Highland offer excellent scenic views, particularly those incorporating the Walkway Over the Hudson. Routes like the Walkway Over the Hudson – Dutchess Rail Trail loop from Highland provide panoramic views of the Hudson River and surrounding landscapes.
Yes, experienced cyclists can find more challenging options. The Walkway Over the Hudson – Dutchess Rail Trail loop from Poughkeepsie is a difficult 73.7-mile (118.6 km) path with significant elevation gain, offering extensive views and a demanding ride.
Several routes incorporate notable attractions. The Walkway Over the Hudson is a prominent feature on many trails. You can also explore sections of the Dutchess Rail Trail and the historic 1889 Rail Bed Trail, which offer unique historical and natural points of interest.
Yes, many road cycling routes in Highland are designed as loops. Popular examples include the Walkway Over the Hudson – Dutchess Rail Trail loop from Highland and the 1889 Rail Bed Trail – Walkway Over the Hudson loop from Poughkeepsie, both offering convenient circular journeys.
The spring, summer, and fall months generally offer the most pleasant conditions for road cycling in Highland, with milder temperatures and vibrant scenery. Autumn, in particular, provides stunning foliage along the Hudson River.
The area is highly rated by the komoot community, with an average score of 4.75 stars from over 50 reviews. Cyclists often praise the well-maintained rail trails, the breathtaking views from the Walkway Over the Hudson, and the variety of routes catering to all skill levels.
Routes originating from Poughkeepsie, such as the Walkway Over the Hudson – 1889 Rail Bed Trail loop from Poughkeepsie, are often convenient for public transport users, as Poughkeepsie is a major hub with train services.
Winter conditions in Highland can include cold temperatures, ice, and snow, especially on less-trafficked routes. While some main roads may be cleared, rail trails might be less accessible. It's advisable to check local weather and trail conditions before planning a winter ride.


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