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Routes
Gravel rides
United States
New York
Ulster County

Hillside

The best gravel rides around Hillside

81

riders

2

rides

Gravel biking around Hillside features routes that often utilize former railway lines, offering varied terrain. The landscape includes historic railway bridges and trestles, providing unique structural features along the paths. Elevations vary, with some routes featuring significant climbs and others remaining relatively flat. The region also incorporates sections alongside water bodies, such as the Ashokan Reservoir.

Best gravel bike trails around Hillside

  • The most popular gravel bike trail is Nice old railway bridge with a view – Springtown Truss Bridge…

Last updated: May 13, 2026

24

riders

#1.

Awosting Falls – Springtown Truss Bridge loop from Rosendale

74.9km

04:19

810m

810m

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Easy gravel ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

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Popular around Hillside

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Tips from the Community

Zachary
January 24, 2025, Awosting Falls

Awosting Falls is always gorgeous, regardless of season and recent rainfall. It is an easy walk from the parking lot with other little falls and pools on the way up, making it a great trail for small kids. You can see the falls from both the top and bottom via a short trail.

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Alex Tray
July 29, 2024, Mountain view

View of the valley and mountains

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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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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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This is the part of the Wallkill Valley Rail Trail which passes through New Paltz. The whole trail is approximately 22 miles in length and was the former Wallkill Valley Railroad. The railroad was closed in 1977 and the first section of trail opened in 1993. This is a multi-user trail, so please respect other trail users.

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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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Frequently Asked Questions

What kind of terrain can I expect on gravel bike trails around Hillside?

Gravel biking around Hillside primarily features routes that utilize former railway lines. You'll encounter varied terrain, including sections alongside water bodies like the Ashokan Reservoir, and paths that cross historic railway bridges and trestles. Elevations vary, offering both relatively flat sections and routes with significant climbs.

Are there any family-friendly gravel bike trails in Hillside?

Yes, Hillside offers options suitable for families. The Ashokan Rail Trail – Frozen Ashokan Reservoir loop from West Hurley is an easy 13.6-mile (21.9 km) path that follows a rail trail alongside the scenic Ashokan Reservoir, making it a great choice for a more relaxed ride.

Where can I find long-distance gravel bike routes near Hillside?

For longer rides, consider routes that incorporate the region's extensive rail trail network. The Nice old railway bridge with a view – Springtown Truss Bridge loop from Town of Rosendale is a challenging 36.7-mile (59.1 km) route with significant elevation gain, offering a substantial gravel biking experience.

What are the difficulty levels of gravel bike trails in Hillside?

The gravel biking network around Hillside offers a range of difficulty levels. You can find easy routes, such as the Ashokan Rail Trail loop, as well as moderate and more difficult options like the Springtown Truss Bridge loop from Town of Rosendale, which features significant elevation.

Are there any circular gravel bike routes in the Hillside area?

Yes, many of the gravel bike routes in Hillside are designed as loops. For example, the Rosendale Trestle Bridge loop from Stockade District is a 32.0-mile (51.5 km) circular trail that takes you through areas featuring the historic Rosendale Trestle Bridge.

What interesting landmarks or viewpoints can I see along the gravel bike trails?

The trails often feature historic railway bridges and offer scenic views. You can ride past the Nice old railway bridge with a view, explore sections of the Ashokan Rail Trail, or even catch glimpses of the Hudson River Overlook on some routes. The Wallkill Valley Rail Trail is another notable feature.

What do other gravel bikers enjoy most about gravel biking in Hillside?

The komoot community highly rates the gravel biking experience in Hillside, with an average score of 5.0 stars. Riders often praise the unique combination of historic railway lines, the varied terrain, and the scenic sections alongside the Ashokan Reservoir and over impressive truss bridges.

Are there any routes that pass by lakes or reservoirs?

Absolutely. The Ashokan Rail Trail – Frozen Ashokan Reservoir loop from West Hurley follows a rail trail directly alongside the Ashokan Reservoir, offering beautiful waterside views. You can also find routes near Onteora Lake.

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

While specific conditions vary, the region's rail trails and varied terrain are generally enjoyable across multiple seasons. Spring and fall often offer pleasant temperatures and vibrant scenery, while summer provides longer daylight hours. Winter riding is possible, especially on well-maintained rail trail sections, but always check local weather and trail conditions.

Are there any advanced gravel bike trails in Hillside for experienced riders?

Yes, experienced riders looking for a challenge will find suitable options. The Nice old railway bridge with a view – Springtown Truss Bridge loop from Town of Rosendale is classified as difficult, covering 36.7 miles (59.1 km) with significant elevation gain, providing a demanding ride.

Where can I find parking for gravel biking trails in Hillside?

Many rail trail access points and trailheads in the Hillside area offer designated parking. For specific routes, it's best to check the tour details on komoot, as they often provide information on starting points and available parking facilities near the trailheads.

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