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Road cycling routes
United States
New York
Dutchess County

Hillside Lake

The best road cycling routes around Hillside Lake

5.0

(20)

681

riders

58

rides

Road cycling around Hillside Lake offers access to an extensive network of multi-use trails within the scenic Hudson Valley. The region is characterized by diverse landscapes, including well-maintained rail trails that traverse rural areas, dense wooded sections, and picturesque water bodies. Cyclists can experience varied terrain, from generally flat former railway beds to rolling countryside, providing options for different fitness levels. These interconnected routes form part of the larger Empire State Trail system, offering continuous and scenic rides.

Best road…

Last updated: June 28, 2026

5.0

(11)

121

riders

#1.

Dutchess Rail Trail – Walkway Over the Hudson loop from Lake Walton Trailhead

42.1km

01:48

280m

280m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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5

riders

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

4

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

3

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Hillside Lake

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Tips from the Community

LuisG
August 24, 2025, Lake view

Should be the top and relatively flat. All downhill either direction

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Air pump!! and some tools at this location.

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Excellent views

Translated by Google

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Elevator goes to the waterfront

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Alex Tray
June 16, 2025, Lake view

Pretty lake on one side and a marsh on the other

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It has tours!

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Alex
September 13, 2024, Walkway Over the Hudson

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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mtm05005
February 25, 2024, Dutchess Rail Trail

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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Frequently Asked Questions

How many road cycling routes are available around Hillside Lake?

The Hillside Lake area offers a wide selection of road cycling routes, with over 50 routes detailed on komoot. These routes cater to various skill levels, from easy to more challenging rides.

What kind of terrain can I expect on road cycling routes in Hillside Lake?

Road cycling around Hillside Lake features diverse landscapes. You'll find well-maintained rail trails that traverse rural areas, dense wooded sections, and picturesque water bodies like Tonetta Lake, Ice Pond, and Whaley Lake. The terrain varies from generally flat former railway beds to rolling countryside, offering options for different fitness levels.

Are there road cycling routes suitable for beginners in Hillside Lake?

Yes, there are several easy road cycling routes perfect for beginners. For instance, the Dutchess Rail Trail loop from Hopewell Junction is an easy 25.3-mile path offering a peaceful cycling experience on a smooth, well-maintained surface through rolling countryside. Another great option is the Whaley Lake – Whaley Lake loop from Fishkill Plains Trail Side Access, an easy 45.7-mile route.

What are some notable viewpoints or landmarks along the road cycling routes?

Many routes offer scenic views and interesting landmarks. The Hudson Valley Rail Trail connects to the famous Walkway Over the Hudson, providing breathtaking panoramic views of the Hudson River and the Catskill Mountains. The Maybrook Trailway also features seasonal waterfalls and crosses the historic Appalachian Trail, winding alongside picturesque lakes.

Are there any circular road bike trails in the Hillside Lake area?

Yes, many routes are designed as loops, allowing you to start and end at the same point. A popular choice is the Whaley Lake – Whaley Lake loop from Lake Walton Trailhead, a 49.5-mile moderate route that winds through rural landscapes and alongside several lakes. The Dutchess Rail Trail – Walkway Over the Hudson loop from Fishkill Plains Trail Side Access is another excellent circular option.

Where can I park when road cycling in Hillside Lake?

Hillside Lake Park serves as a central point with amenities, and its proximity to the trail network suggests it could be a convenient starting point. Many trailheads for the extensive rail trail system, such as Lake Walton Trailhead or Fishkill Plains Trail Side Access, typically offer parking facilities for cyclists.

What do other road cyclists enjoy most about road cycling in Hillside Lake?

The area is highly rated by the komoot community, with an average score of 5.0 stars from over 30 reviews. Cyclists often praise the extensive network of well-maintained rail trails, the diverse and picturesque scenery of the Hudson Valley, and the variety of routes suitable for different abilities.

Are there any family-friendly road cycling routes around Hillside Lake?

Absolutely. The former railway beds, such as sections of the Maybrook Trailway and Dutchess Rail Trail, offer generally flat and smooth surfaces, making them ideal for family outings. These trails provide a peaceful cycling experience away from vehicle traffic, perfect for riders of all ages.

What is the best time of year for road biking in Hillside Lake?

The Hudson Valley region, including Hillside Lake, is beautiful throughout the spring, summer, and fall. Spring brings lush greenery and blooming wildflowers, while autumn offers stunning foliage. Summer is also popular, though it can be warmer. The well-maintained trails are generally accessible during these seasons.

Are there more challenging road cycling routes for experienced riders?

Yes, while many routes are easy to moderate, there are options for more experienced riders. The region's diverse landscapes include rolling countryside and routes with more significant elevation changes. For example, the Whaley Lake – Whaley Lake loop from Lake Walton Trailhead, while moderate, covers nearly 50 miles with over 400 meters of elevation gain, offering a good workout.

Can I connect to larger trail systems from Hillside Lake?

Yes, the interconnected rail trails in the Hillside Lake area, including the Maybrook Trailway, Dutchess Rail Trail, and Hudson Valley Rail Trail, form part of the larger Empire State Trail system. This allows for continuous and scenic routes, offering opportunities for extended rides and exploring beyond the immediate Hillside Lake vicinity.

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