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.
Last updated: June 27, 2026
4
hikers
3.93km
01:02
30m
30m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
2.67km
00:52
170m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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86.4km
22:21
490m
450m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
10
hikers
6.65km
01:42
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
2
hikers
6.31km
01:48
140m
140m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Popular around Hillside Lake
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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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!
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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.
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.
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.
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.
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.
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.
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.
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.
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.
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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