The best road cycling routes around Hillside
4.8
(31)
371
riders
61
rides
Road cycling routes around Hillside are characterized by varied hilly terrain, offering both challenging ascents and rewarding descents. The region features extensive forests, scenic valleys, and routes that often follow the contours of lakes and rivers. Cyclists can expect diverse landscapes, including sections along former rail trails and paths with views of significant water bodies. This topography provides a range of gradients suitable for different road cycling preferences.
Best road cycling routes around Hillside
- The most popular road cycling route is Kingston to Upper Ashokan Reservoir, a 34.4 miles (55.4 km) trail that takes about 2 hours 36 minutes to complete, offering views of the reservoir.
- Another top favourite among local road cyclists is Kingston to Fifth Lake loop via Hurley Mountain Road, a moderate 49.7 miles (80.0 km) path. This route features significant elevation changes and scenic lake views.
- Local road cyclists also love the Kingston to Stone Ridge via Wallkill Valley Rail Trail, a 22.6 miles (36.4 km) trail leading through a converted rail path, often completed in about 1 hour 39 minutes.
- Road cycling around Hillside is defined by hilly landscapes, extensive forests, and routes along lakes and rivers. The network offers options for easy, moderate, and difficult ability levels.
- The routes in Hillside are highly rated by the komoot community with an average score of 4.6 stars from more than 30 reviews. More than 300 road cyclists have used komoot to explore Hillside's varied terrain.
Last updated: May 1, 2026
4.6
(5)
15
riders
55.4km
02:37
380m
380m
Cycle 34.4 miles from Kingston to the Upper Ashokan Reservoir, enjoying Catskill views and the Ashokan Rail Trail's crushed stone surface.
13
riders
80.0km
03:52
650m
650m
Cycle the moderate 49.7-mile Kingston to Fifth Lake loop via Hurley Mountain Road, gaining 2125 feet in Ulster County.
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12
riders
36.4km
01:39
280m
280m
Cycle the moderate 22.6-mile Wallkill Valley Rail Trail from Kingston towards Stone Ridge, enjoying scenic views and the Rosendale Trestle.
4.5
(4)
13
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(2)
14
riders
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
This massive reservoir spans more than 8,000 acres and, depending on who you talk to, is somewhere around 180 to 190 feet deep. It makes for great scenery on your ride or, if you're really feeling ambitious, you could pack a travel fishing pole and try your hand for brown and rainbow trout. (Make sure you check local fishing regulations before getting your line wet!)
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The Rosendale Trestle Bridge, situated along the Wallkill Valley Rail Trail, is famous for providing a breathtaking view of the Rosendale area and the Roundout Creek. It's recommended to ride slowly across the bridge due to some boards needing maintenance.
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Head north off of the road for a couple of minutes to find the pretty waterfall. A great spot to take a shaded break off of the bike and cool off.
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The Wallkill Valley Rail Trail totals roughly 22 miles in one direction. The path follows an old railroad line and is primarily packed-gravel surface the entire time. This is a multiuse trail, so be prepared to see other users on the trail. This particular section travels from the northern terminus just outside of Kingston down to Joppenbergh Mountain Park. The Rosendale Trestle Bridge just to the south of Joppenbergh Mountain is one of the more scenic viewpoints along the entire Wallkill Valley Rail Trail.
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Fifth Lake is a small yet tranquil lake just outside Rosendale in Ulster County.
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The Springtown Truss Bridge crosses the Wallkill River. It was once formed part of the Wallkill Valley Railroad, running between Ulster County and New York City. The bridge was originally built in 1870 and made of wood, but was rebuilt using iron in the early 1880s.
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The Springtown Truss Bridge crosses the Wallkill River. It was once formed part of the Wallkill Valley Railroad, running between Ulster County and New York City. The bridge was originally built in 1870 and made of wood, but was rebuilt using iron in the early 1880s.
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The Springtown Truss Bridge crosses the Wallkill River. It was once part of the Wallkill Valley Railroad, running between Ulster County and New York city. The bridge was originally built in 1870 and made of wood, but was rebuilt using iron in the early 1880s.
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Frequently Asked Questions
How many road cycling routes are available around Hillside?
Hillside offers a wide variety of road cycling routes, with over 50 different tours available. These routes cater to various skill levels, including easy, moderate, and challenging options.
What makes road cycling in Hillside unique?
Road cycling in Hillside is characterized by its varied hilly terrain, providing both challenging ascents and rewarding descents. The region features extensive forests, scenic valleys, and routes that often follow the contours of lakes and rivers, offering diverse landscapes and breathtaking panoramic views.
Are there challenging road cycling routes in Hillside?
Yes, Hillside offers several challenging road cycling routes. The hilly landscapes provide significant elevation changes, perfect for cyclists looking to test their endurance. For example, the Kingston to Fifth Lake loop via Hurley Mountain Road is a moderate route with significant elevation changes over its 49.7 miles.
Can beginners find suitable road cycling routes in Hillside?
Absolutely. While Hillside is known for its hills, there are 11 easy road cycling routes available. These routes often feature gentler gradients and can include sections along former rail trails, providing a more relaxed cycling experience for beginners.
What scenic viewpoints or landmarks can I expect on road cycling routes in Hillside?
Many routes in Hillside offer stunning views and pass by notable landmarks. You might encounter picturesque water bodies like Onteora Lake, or enjoy views from a nice old railway bridge with a view. The Hudson River Overlook also provides a fantastic vista.
Are there road cycling routes that follow lakes or rivers?
Yes, Hillside's topography often includes routes that follow the contours of lakes and rivers, offering picturesque backdrops. The Kingston to Upper Ashokan Reservoir route, for instance, provides beautiful views of the reservoir.
Are there any long-distance road cycling options in Hillside?
For those seeking longer rides, Hillside has several options. Routes like the Rosendale Trestle Bridge – Springtown Truss Bridge loop from Stockade District cover over 50 miles, offering extensive exploration of the region's diverse terrain.
What do other cyclists say about the road cycling routes in Hillside?
The road cycling routes in Hillside are highly rated by the komoot community, with an average score of 4.6 stars from nearly 40 reviews. Cyclists often praise the varied terrain, scenic beauty, and the mix of challenging climbs and rewarding descents.
Are there circular road cycling routes available in Hillside?
Yes, many of the routes in Hillside are designed as loops, allowing cyclists to start and finish in the same location. An example is the Kingston to Fifth Lake loop via Hurley Mountain Road, which offers a comprehensive tour of the area.
Are there any routes that utilize former rail trails for road cycling?
Yes, Hillside features routes that incorporate converted rail paths, providing smoother sections and unique historical perspectives. The Kingston to Stone Ridge via Wallkill Valley Rail Trail is a great example, offering a scenic ride along the Wallkill Valley Rail Trail.
What kind of natural features can I expect to see while cycling in Hillside?
Hillside's routes often traverse extensive forests, offering shaded sections and a sense of immersion in nature. You'll also encounter diverse geological formations, valleys, and potentially distant mountain views, depending on the specific route.
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