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Routes
Hikes
United States
New York
Ulster County

Hillside

The best walks and hikes around Hillside

4.5

(8)

73

hikers

12

hikes

Hiking trails around Hillside feature a diverse landscape, including lake loops, rail trails, and paths through wild forests and preserves. The region offers varied terrain, from gentle lakeside strolls to more challenging routes with moderate elevation changes. Many trails follow former railway lines, providing relatively flat and accessible paths.

Best hiking trails around Hillside

  • The most popular hiking route is Onteora Lake Trail loop — Bluestone Wild Forest, a 3.8 miles (6.1 km) trail that takes 1 hour 35…

Last updated: May 10, 2026

1

hikers

#1.

Hudson River Brickyard Trail

1.34km

00:22

30m

10m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

Hard

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Popular around Hillside

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Tips from the Community

Alex Tray
July 29, 2024, End of the Wallkill Trail

Intersection with road. Can see that there is more trail being built.

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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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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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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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This is a convenient place to access the Jockey Hill mountain bike trails. There are multiple mountain biking and hiking trails here, of varying levels of difficulty.

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In this National Historic Landmark District, there are 7 historic stone-house museums, a reconstructed church from 1717, an old burying ground and a replica Esopus Munsee wigwam. This is a great outdoor museum to explore. Keep an eye out for the blue and yellow signs, which provide information on the different buildings.

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Frequently Asked Questions

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

Hiking around Hillside offers a diverse landscape. You'll find trails ranging from relatively flat former railway lines, like the Kingston Point Rail Trail, to paths through wild forests and preserves with moderate elevation changes. Many routes feature lake loops and scenic viewpoints.

Are there any easy hiking trails suitable for beginners in Hillside?

Yes, Hillside has several easy trails. For instance, the Onteora Lake Trail loop is an easy 3.8-mile route offering pleasant views. Another accessible option is the Lighthouse Park & Esopus Meadows Preserve loop, which is shorter and generally flat.

What are some interesting landmarks or natural features to see along the trails?

The Hillside area is rich in natural beauty and points of interest. You can enjoy views of Onteora Lake, explore sections of the Ashokan Rail Trail, or discover the Wallkill Valley Rail Trail. There's also a nice old railway bridge with a view and the Hudson River Overlook for panoramic vistas.

Are there any circular hiking routes in the Hillside area?

Yes, you'll find circular routes in Hillside. A popular option is the Onteora Lake Trail loop, which provides a complete circuit around the lake. Another loop trail is the Joppenbergh Mountain Trail loop, offering a different perspective of the landscape.

What do other hikers enjoy most about the trails in Hillside?

The hiking trails in Hillside are highly rated by the komoot community, with an average score of 4.5 stars. Hikers often praise the varied terrain, from serene lake loops to engaging rail trails, and the opportunity to explore wild forests and preserves. The accessibility of many routes also receives positive feedback.

Are the hiking trails in Hillside suitable for families with children?

Many trails in Hillside are family-friendly, especially the easier routes. The rail trails, such as the Kingston Point Rail Trail, offer relatively flat surfaces that are great for younger hikers. The Onteora Lake Trail loop is also a good choice for a family outing.

Can I bring my dog on the hiking trails in Hillside?

Generally, many trails in the Hillside area are dog-friendly, but it's always best to check specific trail regulations before you go. Most public lands and rail trails welcome leashed dogs. Please ensure your dog is under control and you clean up after them to preserve the natural environment for everyone.

What is the best time of year to go hiking in Hillside?

Hillside offers enjoyable hiking throughout much of the year. Spring brings lush greenery and blooming wildflowers, while autumn showcases vibrant fall foliage, making it a particularly popular time. Summer is great for longer days, though some trails might be more exposed. Winter hiking is possible, especially on the flatter rail trails, but be prepared for colder conditions and potential snow or ice.

Are there any cafes or places to eat near the hiking trails?

While specific cafes directly on every trailhead might be limited, the towns and villages surrounding Hillside, such as Kingston and Rosendale, offer various dining options. After completing a hike like the Wallkill Valley Rail Trail to Rosendale Trestle Bridge, you'll find places to refuel nearby.

Are there public transport options to reach the trailheads in Hillside?

Public transport options to specific trailheads in Hillside can vary. While some areas might be accessible by local bus services, many trailheads are best reached by car. It's advisable to research local bus routes and schedules in advance if you plan to rely on public transport to access the more remote trails.

Is parking available at the Hillside trailheads?

Parking is generally available at the main trailheads for popular routes in Hillside. For example, trails like the Kingston Point Rail Trail typically have designated parking areas. However, during peak seasons or busy weekends, these lots can fill up quickly, so arriving early is recommended.

Most popular routes around Hillside

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