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Routes
Cycling routes
United States
New York
Ulster County

Hillside

The best cycling routes around Hillside

4.6

(12)

243

riders

31

rides

If you've ever tried to plan touring cycling around Hillside, you know how quickly the sheer number of routes can become overwhelming. It's tough to tell which ones are genuinely worth your time and effort, and which are just filler. That's where we come in. Our komoot community has ridden, mapped, and reviewed countless routes here, and we've curated this guide to save you the guesswork and point you straight to the rides that truly deliver.

Touring cycling around Hillside…

Last updated: May 29, 2026

#1.

Wallkill Valley Rail Trail Loop

47.5km

02:58

340m

340m

The Wallkill Valley Rail Trail Loop offers a delightful touring cycling adventure through the heart of Ulster County, New York. You'll pedal along a mix of hard-packed gravel and paved…

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Moderate

2

riders

17.3km

01:26

110m

110m

The Kingston Greenline Trail offers a unique touring cycling experience, blending urban exploration with waterfront views. You'll pedal past historic sites like the Hutton Brickyards and enjoy glimpses of the…

Easy
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Embark on the Ashokan Reservoir Promenade loop from Kingston for a truly spectacular touring bicycle experience, blending smooth paved sections with challenging crushed stone and hilly roads. This difficult 33.5-mile…

Hard

The Onteora Lake loop from Kingston offers a delightful escape into nature, blending paved roads with scenic off-road trails. You'll cycle through mixed hardwood and conifer forests, enjoying tranquil views…

Moderate

This touring cycling route offers a delightful journey along the Wallkill Valley Rail Trail, showcasing diverse scenery from woodlands to open fields. The star of the show is the Rosendale…

Moderate
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Popular around Hillside

Hiking around Hillside

Road Cycling Routes around Hillside

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Gravel biking around Hillside

Tips from the Community

Alex Tray
July 29, 2024, Cold Air Cave

Vents cold air which is really refreshing on a hot day.

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Almost like a ruined medieval fortress

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Sam
May 7, 2024, Onteora Lake

Trail hike around a lake. Be sure you have GPS with you could get lost. Trail not marked except by foot path.

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Beautiful and peaceful. Very little shade so dress accordingly.

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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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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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Matthew
January 15, 2024, Rosendale Trestle

The Rosendale Trestle Bridge is a famous bridge crossing along the Wallkill Valley Rail Trail between Joppenbergh Mountain Park and Hardenbergh Park. This wooden boards making the base of the bridge are a little weathered, so watch your footing as you cross.

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Scenic road that runs right next to the Ashokan Reservoir. Great views of the Reservoir and the Catskill Mountains.

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Frequently Asked Questions

How many touring cycling routes are available in Hillside?

There are over 20 touring cycling routes in the Hillside region, offering a variety of experiences from easy rides to more challenging loops. The komoot community has explored more than 150 of these routes.

What is the best season for touring cycling in Hillside?

The Hillside region is enjoyable for touring cycling across multiple seasons. Spring and fall offer pleasant temperatures and scenic foliage, especially along river valleys and rail trails. Summer is also popular, though some routes might be busier. Winter cycling is possible, particularly on well-maintained rail trails, but always check local conditions.

Are there easy touring cycling routes suitable for beginners in Hillside?

Yes, Hillside offers several easy touring cycling routes perfect for beginners. For instance, the Kingston Greenline Trail is an accessible 10.7-mile path that follows a converted rail line, providing a relatively flat experience. Another option is the Rondout Creek loop from Kingston, which is also considered easy.

Are there family-friendly touring cycling routes in Hillside?

Many of Hillside's touring cycling routes are suitable for families, especially those utilizing converted rail trails which tend to be flatter and separated from vehicle traffic. The Kingston Greenline Trail is an excellent choice for families due to its easy grade and accessible nature.

What can I see along the touring cycling routes in Hillside?

Hillside's touring cycling routes offer diverse scenery. You can expect views of the Hudson River, Rondout Creek, and rolling hills. Notable attractions include the Nice old railway bridge with a view, Onteora Lake, and the Hudson River Overlook. Many routes also follow scenic rail trails like the Ashokan Rail Trail and the Wallkill Valley Rail Trail.

Are there any circular touring cycling routes in Hillside?

Yes, Hillside features several circular touring cycling routes. A popular option is the Hudson River and Hussey Hill loop from Kingston, which offers river views and incorporates some hills. Another well-liked circular route is the Wallkill Valley Rail Trail Loop, providing a scenic ride through a rail trail corridor.

Where can I find parking for touring cycling routes in Hillside?

Parking availability varies by trailhead. Many rail trail access points and popular starting locations in towns like Kingston offer designated parking areas. It's advisable to check specific route details or local municipality websites for parking information before you head out.

Are there cafes or places to stop for refreshments along the touring cycling routes?

While specific cafes are not listed for every route, many touring cycling routes in Hillside pass through or near towns and villages where you can find cafes, restaurants, and convenience stores for refreshments. Routes along the Hudson River or through Kingston will offer more options.

What should I bring for a touring cycling trip in Hillside?

For a touring cycling trip in Hillside, essential items include a helmet, water bottles, snacks, a basic repair kit (spare tube, pump, tire levers), and appropriate clothing for the weather. Sunscreen, sunglasses, and a charged phone with navigation are also highly recommended. For longer rides, consider a small first-aid kit.

What do other touring cyclists enjoy most about touring cycling in Hillside?

The touring cycling routes in Hillside are highly rated by the komoot community, with an average score of 4.6 stars. Reviewers often praise the diverse landscape, including scenic river valleys and well-maintained converted rail trails. The variety of routes, from easy paths to more challenging loops, is also frequently highlighted.

Are touring cycling routes in Hillside dog-friendly?

Many rail trails and multi-use paths in Hillside are dog-friendly, provided dogs are kept on a leash and owners clean up after them. However, specific regulations can vary by trail or park. Always check local signage or official websites for the most current rules regarding pets on specific routes.

Are there less crowded touring cycling routes in Hillside?

While popular routes like the Kingston Greenline can see more activity, especially on weekends, Hillside offers many less-traveled options. Exploring routes during off-peak hours (weekdays, early mornings) or choosing some of the longer, more challenging loops can lead to a quieter experience. The region has over 20 routes, so there's ample opportunity to find a peaceful ride.

Can I go touring cycling in Hillside during winter?

Yes, touring cycling in Hillside is possible during winter, especially on paved rail trails that are often cleared or remain passable. However, be prepared for colder temperatures, potential ice or snow, and shorter daylight hours. Routes with significant elevation changes or unpaved sections might be more challenging. Always check weather conditions and trail reports before heading out.

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