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Hillside

Attractions and Places To See around Hillside - Top 15

Best attractions and places to see around Hillside include a variety of natural and recreational features, particularly in the area near Rosendale, New York. This region is characterized by its extensive multi-use rail trails, tranquil lakes, and scenic viewpoints. Visitors can explore former railway lines converted into paths, offering opportunities for hiking and cycling. The landscape also features forests and rivers, providing diverse outdoor experiences.

Best attractions and places to see around Hillside

  • The most popular attractions is Nice old…

Last updated: May 5, 2026

Nice old railway bridge with a view

Highlight • Bridge

Great view of the Rosendale area. The boards are a little uneven and need a little maintenance.

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Onteora Lake

Highlight • Lake

Onteora Lake is a small lake which is great for watersports. This is a lovely tranquil setting, great for a rest stop and a picnic.

Originally, the lake was created …

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Ashokan Rail Trail

Highlight • Trail

The Ashokan Rail Trail is a great multi-use trail, that has a compact surface. This trail runs beside the Ashokan Reservoir. It is open during daylight hours.

There are parking areas and restrooms at the trailheads.

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Wallkill Valley Rail Trail

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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 …

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Hudson River Overlook

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This viewpoint gives you a nice lookout over the trees, extending all the way to the Hudson River in the near distance. Shaupeneak Mountain is behind you.

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Tips from the Community

Janine & Marcel
July 30, 2025, Ashokan Rail Trail

Beautiful rail trail with parking at both ends.

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You cycle the entire route through the forest. The path is easy to cycle and, with its bridges, offers wonderful natural surroundings. There are parking spaces at both the beginning and the end.

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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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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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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 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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Lisa
January 13, 2024, Hudson River Overlook

This viewpoint gives you a nice lookout over the trees, extending all the way to the Hudson River in the near distance. Shaupeneak Mountain is behind you.

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Frequently Asked Questions

What are the best outdoor attractions near Hillside, New York?

The Hillside area, particularly near Rosendale, New York, is rich in natural and recreational features. Top outdoor attractions include the Wallkill Valley Rail Trail, known for its scenic views and the iconic Rosendale Trestle Bridge. The Ashokan Rail Trail offers a compact surface for cycling and walking beside the Ashokan Reservoir. For watersports and tranquil settings, Onteora Lake is a popular choice.

Are there any scenic viewpoints in the Hillside area?

Yes, the Rosendale Trestle Bridge along the Wallkill Valley Rail Trail offers great views of the Rosendale area. Additionally, the Hudson River Overlook provides a nice lookout over the trees, extending to the Hudson River.

What kind of trails can I find around Hillside for hiking and cycling?

The Hillside area is well-known for its multi-use rail trails. The Wallkill Valley Rail Trail is a 22-mile path following an old railroad line, primarily packed-gravel, suitable for both cycling and walking. The Ashokan Rail Trail is another excellent option, offering a compact surface for cycling and walking through the forest beside the Ashokan Reservoir.

Are there family-friendly activities or trails available in Hillside?

Absolutely. Many of the rail trails, such as the Ashokan Rail Trail and the Wallkill Valley Rail Trail, are considered family-friendly due to their relatively flat, multi-use surfaces. Onteora Lake also offers a tranquil setting for picnics and gentle walks, making it suitable for families.

Where can I go for watersports or a tranquil lakeside experience near Hillside?

For watersports and a peaceful lakeside experience, Onteora Lake is an excellent choice. It's a small lake perfect for watersports, rest stops, and picnics, with mountain biking and hiking trails nearby.

Are there any trails suitable for mountain biking in the Hillside area?

Yes, Onteora Lake features mountain biking trails of varying difficulty levels. The Ashokan Rail Trail, while primarily for cycling and walking, also offers a suitable surface for mountain biking.

What are the options for easy hikes near Hillside?

For easy hikes, you can explore routes like the Onteora Lake Loop Trail (approximately 6 km) or the Red Trail (around 2.3 km). The Hudson River Brickyard Trail is another easy option at about 1.3 km. These trails offer accessible paths for a relaxed outdoor experience.

Is the Wallkill Valley Rail Trail accessible, and what should I know about it?

The Wallkill Valley Rail Trail is a multi-use path totaling roughly 22 miles in one direction. It follows an old railroad line and is primarily a packed-gravel surface. The Rosendale Trestle Bridge is a notable scenic viewpoint along this trail. Parking areas are available at various points along the trail, including at trailheads for the Ashokan Rail Trail which connects to the wider network.

What outdoor activities can I do near these attractions?

Beyond exploring the attractions themselves, the Hillside area offers a variety of outdoor activities. You can enjoy hiking on trails like the Onteora Lake Loop Trail or the Wallkill Valley Rail Trail. Road cycling is also popular, with routes such as the Kingston to Upper Ashokan Reservoir. Watersports are available at Onteora Lake.

What do visitors enjoy most about the Hillside attractions?

Visitors particularly appreciate the scenic beauty and the accessibility of the trails. The Rosendale Trestle Bridge is frequently highlighted for its great views. The multi-use nature of trails like the Ashokan Rail Trail is also highly valued, offering pleasant cycling and walking experiences through natural surroundings.

Are there any hidden gems or unique spots to discover in the Hillside area?

While not explicitly 'hidden,' the Rosendale Trestle Bridge, with its slightly weathered wooden boards, offers a unique historical charm as part of the Wallkill Valley Rail Trail. The tranquil setting of Onteora Lake, originally created by damming the Esopus Creek, provides a serene escape that some might consider a local gem.

What is the best time to visit Hillside attractions?

Based on general outdoor activity recommendations for the region, the best time to visit is typically from March to October. During these months, the weather is generally pleasant, making it ideal for hiking, cycling, and watersports, and you can often enjoy blooming wildflowers.

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