The best road cycling routes around Highland
4.7
(36)
819
riders
12
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.
Best road cycling routes around Highland
- The most popular road cycling route is Walkway Over the Hudson – Dutchess Rail Trail loop…
Last updated: October 19, 2026
5.0
(3)
41
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
69.0km
03:28
630m
630m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
16.8km
00:50
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
11
riders
84.0km
03:39
560m
560m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5
riders
75.1km
03:34
570m
570m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Tips from the Community
Pedestrian and bicycle bridge over the Hudson. Very long bridge with great views.
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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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Berean Park is a lovely place to visit, with a beach on one of the ponds. There are various facilities, including picnic tables, a snack bar and bathroom facilities.
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This red bridge is a great place to take in the views of the Rondout Creek. Rondout Creek is a tributary of the Hudson River and flows through Rondout Reservoir. The reservoir is an important water source for New York City.
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The Hudson Valley Rail Trail offers access to the Walkway Over the Hudson, which is pretty much just a pedestrian-only bridge open to runners, walkers, and cyclists. You get pretty great views of the river from the crossing, and there are nice facilities at the trailheads on both sides of the bridge.
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Frequently Asked Questions
How many road cycling routes are available in Highland?
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.
What types of terrain can I expect on road cycling routes in Highland?
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.
Are there easy road cycling routes suitable for beginners in Highland?
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.
Which road cycling routes offer the best scenic viewpoints in Highland?
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.
Are there challenging road cycling routes for experienced cyclists in Highland?
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.
What attractions can I see along the road cycling routes in Highland?
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.
Are there any circular road cycling routes in Highland?
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.
When is the best time of year to go road cycling in Highland?
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.
What do other road cyclists enjoy most about road cycling in Highland?
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.
Are there road cycling routes in Highland that are accessible by public transport?
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.
What are the typical conditions for road cycling in Highland during winter?
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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