5.0
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39
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Hikes around Sherman are characterized by dense woodlands, rolling hills, and routes that often incorporate sections of the Appalachian Trail. The landscape offers a mix of lakeside paths and more challenging forest treks with significant elevation changes. This network of Sherman hiking trails provides options for various ability levels, from easy loops to demanding long-distance hikes.
Last updated: June 23, 2026
6
hikers
6.55km
02:01
200m
240m
The Pootatuck State Forest Loop offers a tranquil escape into a landscape of rugged, wooded slopes and fascinating rock formations. As you hike, you'll traverse shaded paths, old charcoal-wagon roads,…
1
hikers
5.87km
01:37
100m
90m
The Cranberry Mountain Trail offers a delightful and varied hiking experience, winding through lush forests and crossing serene streams before opening up to panoramic views of the Hudson Valley. This…

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2
hikers
6.92km
02:06
220m
230m
The Pine Hill to Squantz Pond Loop offers a fantastic escape into a
1
hikers
3.84km
01:05
80m
80m
The Deer Pond Farm: Bobcat Loop offers an easy and engaging hike through a tapestry of meadows, wetlands, and woodlands, dotted with historic stone walls. You'll experience the diverse habitats…
7.30km
02:10
270m
100m
Hike the moderate Quaker Lake via Appalachian Trail and Red Trail, covering 4.5 miles with 882 feet of elevation gain in Pawling Nature Rese
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Yes, there are several options for easier outings. For a shorter walk, consider the Squantz Pond State Park loop. It's a relatively flat 2.3-mile (3.8 km) trail that's great for a quick nature escape with the family.
For a strenuous and rewarding day on the trail, the Gardner Hill – Tenmile Hill loop from Wingdale is an excellent choice. This 16.5-mile (26.6 km) route involves significant elevation gain and will take most of a day, offering a true test of endurance through the region's woodlands.
The hiking is characterized by dense woodlands, rolling hills, and sections of the Appalachian Trail. You can expect a mix of lakeside paths and more rugged forest treks with notable changes in elevation. Trails are typically on natural surfaces with roots and rocks.
Absolutely. Many of the best routes are loops, so you can end your hike where you started without backtracking. A great moderate option is the Cats Rock loop from Appalachian Trail, which offers a varied experience over 6.4 miles (10.3 km).
In general, dogs are welcome on many trails in the area, but they must be kept on a leash. State parks and specific trail networks may have their own regulations, so it's always a good practice to check the rules for the specific park or preserve you plan to visit before you go.
For any hike, bring plenty of water and snacks. Sturdy hiking shoes with good grip are essential for the area's hilly and sometimes rocky terrain. We also recommend packing layers of clothing, as weather can change, along with a map or a fully charged phone with the route downloaded for navigation.
Spring and autumn are fantastic times to hike here. Spring offers budding trees and pleasant temperatures, while autumn provides spectacular fall foliage and cooler weather. Summer can be hot and humid, so plan for early morning starts. Winter hiking is possible but requires proper gear for snow and ice.
There are a handful of curated, top-rated routes in this guide, but the broader area contains a much larger network of trails. Komoot users have explored and shared dozens of routes, showcasing the variety of hiking available.
The area is highly rated by the komoot community. Hikers often praise the serene woodland settings, the sense of immersion in nature, and the challenge provided by the rolling hills. Access to well-maintained sections of the famous Appalachian Trail is also a major highlight for many.
Yes, if you're looking for a trail with significant climbing, the Tenmile Hill – Gardner Hill loop from Tenmile Hill is a great moderate choice. At 7.7 miles (12.5 km) with over 1,400 feet of elevation gain, it provides a solid workout through the woods.
Most trailheads in this region are accessed by car and have designated parking areas. However, lots for popular trails, especially those on the Appalachian Trail, can fill up quickly on weekends. It's always a good idea to arrive early to secure a spot.


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