The best walks and hikes around Village of Montgomery
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Hiking around Village of Montgomery, located in New York's Hudson Valley, features a network of trails winding through state forests, county parks, and along former rail lines. The landscape includes woodlands, lakes, and rivers, offering diverse environments for outdoor exploration. This area provides a mix of natural surface paths and converted rail trails, catering to various hiking preferences.
Best hiking trails around Village of Montgomery
- The most popular hiking route is Diamond Lake loop — Winding Hills County Park,…
Last updated: May 17, 2026
8.62km
02:15
60m
70m
Hike the moderate 5.4-mile Orchard, Drakes, Windsor, and Camp Trail Loop in Stewart State Forest, featuring varied terrain and a scenic pond
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hikers
4.63km
01:13
30m
30m
Hike the easy 2.9-mile (4.6 km) Winding Hills Park Loop, featuring tranquil Diamond Lake views and wooded paths in Montgomery, NY.
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15.7km
04:01
60m
60m
Hike the Walden-Wallkill Rail Trail from Wooster Memorial Grove Park, an accessible 9.7-mile paved path through woods and fields.
11.2km
02:56
80m
90m
Hike the 7.0-mile Pine Root Trail & Ridge Road loop in Stewart State Forest, a moderate route through diverse woodlands and wetlands.
10.4km
02:45
100m
100m
Hike the Drakes, White Cloud, Orchard, and Sara's Way Loop, a moderate 6.4-mile trail in Stewart State Forest, taking around 2 hours 44 minu
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Tips from the Community
Ridge Road is one of a few roads within Stewart State Forest. The roads are a mix of pavement, dirt, and gravel and are really popular for hiking, running, and biking. The singletrack trails definitely give you more of a feeling of being in nature, but you can walk at a better clip on the roads.
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Whether you are looking for wide and smooth roads or tight singletrack trails, Stewart State Forest probably has it. This section of Drakes Trail is one of the most southern singletrack trails in the trail system. The paths cross over each other and over the service roads in the forest, so you can create an almost endless number of loops.
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Stewart State Forest, nestled in Orange County, New York, this expansive forest seamlessly blends wetlands, fields, and forest. With 22 miles of gravel roads and 18 miles of hiking trails, it's a haven for outdoor enthusiasts. Engage in hiking, biking, horseback riding, hunting, cross country skiing, snowmobiling, bird watching, and fishing. Encounter a diverse wildlife population, from white-tailed deer and coyotes to bobcats, wild turkeys, great blue herons, and majestic hawks.
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Diamond Lake is a small reservoir just a few acres in size that serves as the centerpiece of Winding Hills County Park. There are boat rentals available, campsites within a park campground, and a few miles of hiking trails to explore within the park. The main path hugs the lake on the northern banks while it's mostly a road walk if you want to walk along the southern shore.
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This extension of the Walden-Wallkill Rail Trail is a much tighter trail and is unpaved. It isn't super rugged, but there are some roots and rocks along the trail that make it more technical than its longer and paved counterpart to the south.
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This longer section of the Walden-Wallkill Rail Trail is completely paved and is pretty flat. Since it follows an old train line, it technically climbs slightly uphill in one direction and is completely downhill when traveling in the other direction.
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This extension of the Walden-Wallkill Rail Trail is a much tighter trail and is unpaved. It isn't super rugged, but there are some roots and rocks along the trail that make it more technical than its longer and paved counterpart to the south.
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This longer section of the Walden-Wallkill Rail Trail is completely paved and is pretty flat. Since it follows an old train line, it technically climbs slightly uphill in one direction and is completely downhill when traveling in the other direction.
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Frequently Asked Questions
How many hiking trails are available around the Village of Montgomery?
The Village of Montgomery area offers a good selection of hiking opportunities, with over 5 distinct trails documented on komoot. These routes vary in length and difficulty, providing options for different preferences.
Are there easy hiking trails suitable for beginners or families?
Yes, there are several easy trails perfect for beginners or families. For instance, the Diamond Lake loop — Winding Hills County Park is an easy 2.9-mile (4.6 km) loop that offers scenic views around the lake in a county park setting.
What kind of landscapes can I expect to see while hiking near Village of Montgomery?
Hiking around the Village of Montgomery, located in New York's Hudson Valley, features diverse landscapes including woodlands, lakes, and rivers. Trails wind through state forests, county parks, and along former rail lines, offering a mix of natural surface paths and converted rail trails.
Are there any long-distance or moderate trails for more experienced hikers?
Absolutely. For those seeking a longer, moderate challenge, the Walden-Wallkill Rail Trail — Wooster Memorial Grove Park is a 9.7-mile (15.7 km) path following a former rail line, providing a relatively flat and accessible route through varied terrain. Another moderate option is the Pine Root Trail & Ridge Road loop — Stewart State Forest, which is 7.0 miles (11.2 km) through dense woodlands.
What are some notable natural features or attractions along the hiking routes?
Hikers can explore several interesting natural features. You might encounter the serene Diamond Lake within Winding Hills County Park, or the extensive Stewart State Forest. The Shawangunk-Walden-Wallkill Rail Trail itself is a significant feature, offering a unique hiking experience. Additionally, the Streams of Highland Lakes State Park provide beautiful aquatic scenery.
Are there any circular hiking routes available?
Yes, several circular routes are available. The Diamond Lake loop — Winding Hills County Park is a popular easy loop. For a moderate option, consider the Orchard, Drakes, Sarass Way, & White Cloud Trail loop — Stewart State Forest, or the Tamms Pond, Highland Lake & Beaver Pond loop— Highland Lakes State Park.
What is the typical duration for hikes in this area?
Hikes in the Village of Montgomery area vary in duration. Easy loops like the Diamond Lake trail can take around 1 hour 12 minutes. Longer, moderate routes such as the Walden-Wallkill Rail Trail can take over 4 hours, while others like the Pine Root Trail & Ridge Road loop typically take around 3 hours.
Is the Village of Montgomery area suitable for dog-friendly hiking?
Many trails in state forests and county parks in the Hudson Valley region generally permit dogs, often requiring them to be on a leash. It's always best to check specific park regulations for the most up-to-date information before heading out with your canine companion.
What do other hikers enjoy most about hiking in Village of Montgomery?
Hikers using komoot frequently praise the varied terrain and the peaceful natural settings found in the Village of Montgomery area. The network of trails offers options for different ability levels, from easy loops around lakes to moderate paths through extensive woodlands, making it appealing to a wide range of outdoor enthusiasts.
Are there any trails that offer viewpoints or scenic overlooks?
While specific named viewpoints are not detailed for every trail, routes through areas like Winding Hills County Park and Highland Lakes State Park, especially those around lakes and ponds, offer beautiful scenic vistas. The diverse woodlands and open sections of rail trails also provide pleasant views of the surrounding natural environment.
What is the best time of year to go hiking in the Village of Montgomery?
The Hudson Valley region, including the Village of Montgomery, offers beautiful hiking experiences throughout the year. Spring brings lush greenery and wildflowers, summer provides shaded trails, and autumn is particularly stunning with vibrant fall foliage. Winter hiking can also be enjoyed, especially on well-maintained rail trails, though conditions may require appropriate gear.
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