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.
Last updated: May 10, 2026
1
hikers
1.34km
00:22
30m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.00km
01:02
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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35.2km
09:04
180m
150m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
6.14km
01:41
90m
90m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
2.92km
00:48
50m
30m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Intersection with road. Can see that there is more trail being built.
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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.


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