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Routes
Hikes
United States
New York
Dutchess County

Hillside Lake

The best walks and hikes around Hillside Lake

16

hikers

4

hikes

Hiking around Hillside Lake, located in Dutchess County, New York, offers access to a variety of trails surrounding a small lake. The region features a mix of forested areas and open landscapes, with some trails providing views of the Hudson River Valley. The terrain includes gentle inclines and more challenging ascents, catering to different hiking preferences.

Best hiking trails around Hillside Lake

  • The most popular hiking route is Red Wing Lakes Loop, an easy 2.4 miles (3.9 km) trail that takes 1 hour to complete. This route features a scenic overlook within the Red Wing Recreation Area.
  • Another top favourite among local hikers is Appalachian Trail: Hosner Mountain, an easy 1.7 miles (2.7 km) path. This section of the Appalachian Trail offers views of the Hudson River Valley.
  • Local hikers also love the Red Wing Recreation Area loop from Freedom Plains, a 3.9 miles (6.3 km) trail leading through varied terrain, often completed in about 1 hour 48 minutes.
  • Hiking around Hillside Lake is defined by small lakes, forested paths, and sections of the Appalachian Trail. The network offers options for different ability levels, from easy loops to more difficult, longer routes.
  • The guide includes highly-rated routes that showcase the best of the region's landscape. More than 10 hikers have used komoot to explore Hillside Lake's varied terrain.

Last updated: June 27, 2026

4

hikers

#1.

Red Wing Lakes Loop

3.93km

01:02

30m

30m

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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86.4km

22:21

490m

450m

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 Lake

Road Cycling Routes around Hillside Lake

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Tips from the Community

LuisG
August 24, 2025, Lake view

Should be the top and relatively flat. All downhill either direction

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Air pump!! and some tools at this location.

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Alex Tray
June 16, 2025, Lake view

Pretty lake on one side and a marsh on the other

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It has tours!

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Hopewell Junction is the location of the of the junction of the Newburgh, Dutchess and Connecticut railroad line with the New York and New England line. Now, it is the anchor of the Dutchess Rail Trail, a 13 mile long walking and cycling path.

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Buck R-T
July 10, 2022, Whaley Lake

It's along the rail trail. No fishing and no swimming from the trail side.

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Whaley Lake is the largest lake in Dutchess County. So nice to ride here!

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Whaley Lake is the largest lake in Dutchess County. So nice to ride here!

1

0

Frequently Asked Questions

What types of hiking trails can I find around Hillside Lake?

The Hillside Lake area, particularly in New York, offers a range of trails from easy loops to more challenging, longer routes. You'll find accessible paths like the Red Wing Lakes Loop and sections of the Appalachian Trail, as well as extensive routes such as the Maybrook Trailway for those seeking a longer adventure.

Are there any easy, family-friendly hikes near Hillside Lake?

Yes, several easy trails are perfect for families. The Red Wing Lakes Loop is a gentle 3.9 km path with scenic overlooks. Another great option is the Appalachian Trail: Hosner Mountain, which offers beautiful views of the Hudson River Valley over 2.6 km.

Can I find circular hiking routes in the Hillside Lake area?

Absolutely. For a pleasant circular walk, consider the Hiking loop from Lake Walton Trailhead, which covers approximately 6.6 km. Another excellent loop is the Red Wing Recreation Area loop from Freedom Plains, spanning about 6.3 km.

What is the longest hiking trail available around Hillside Lake?

The longest trail in the immediate vicinity is the Maybrook Trailway, which is a challenging route stretching over 86 kilometers. It's ideal for experienced hikers looking for an extended journey.

Are there any trails with significant elevation gain for a more challenging hike?

While many trails are relatively flat, the Appalachian Trail: Hosner Mountain, despite being rated easy, includes a notable ascent of over 170 meters, offering a good workout and rewarding views. For a much longer and more difficult experience, the Maybrook Trailway features nearly 500 meters of elevation gain.

Are there any trails suitable for birdwatching or wildlife spotting?

While specific trails for birdwatching aren't listed in the immediate Hillside Lake, NY area, the broader region offers opportunities. For example, the Hillside Nature Trail at Raystown Lake in Pennsylvania is known for its bird sanctuary and chances to see chipmunks and butterflies. In Alaska, the Middle Fork Loop Trail is prime moose habitat.

What are some notable landmarks or viewpoints along the trails?

The Red Wing Lakes Loop features a scenic overlook. Additionally, the Appalachian Trail: Hosner Mountain provides expansive views of the Hudson River Valley and surrounding counties.

Are there any trails that pass by lakes or offer water views?

Yes, the Red Wing Lakes Loop is situated around the Red Wing Lakes, offering pleasant water views. The Hiking loop from Lake Walton Trailhead also provides access to Lake Walton.

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

The best time to hike around Hillside Lake generally depends on your preference. Spring and fall offer pleasant temperatures and beautiful scenery, with vibrant foliage in autumn. Summer is also popular, though trails can be busier. Winter hiking is possible for those prepared for colder conditions and potential snow.

Are there any trails that are particularly good for beginners?

Beginners will find several excellent options. The Red Wing Lakes Loop and the Appalachian Trail: Hosner Mountain are both rated as easy and are relatively short, making them ideal starting points for new hikers.

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