The best family-friendly hikes and walks in Stewart State Forest
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Family friendly hiking trails in Stewart State Forest traverse a diverse landscape of wetlands, open fields, and dense woodlands in Orange County, New York. The forest covers 6,700 acres, featuring successional fields, former agricultural lands, and numerous ponds. A notable natural feature is the Great Swamp, accessible via a boardwalk, offering a unique ecosystem experience. Elevation changes are generally minimal, making the trails accessible for various skill levels.
Best family friendly hiking trails in Stewart State Forest
- The most popular…
Last updated: May 8, 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
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.
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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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6.83km
01:45
30m
30m
Hike the easy 4.2-mile Chadwick Lake Loop Trail in Newburgh, New York, for scenic lake views and a family-friendly outdoor experience.
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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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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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Chadwick Lake, once a water source for Newburgh, NY, is now a recreational spot with picnic areas, playgrounds, and a 4.2-mile hiking trail. Fishing for largemouth bass is allowed. Despite occasional water quality issues, it's popular among residents for leisure and exercise.
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Frequently Asked Questions
How many family-friendly hiking trails are available in Stewart State Forest?
Stewart State Forest offers a great selection of family-friendly hikes. This guide features 7 routes, ranging from easy strolls to moderate adventures, perfect for getting the whole family outdoors.
What kind of terrain can we expect on family hikes in Stewart State Forest?
The trails in Stewart State Forest are known for their varied and generally gentle terrain. You'll find a mix of woodlands, open fields, and wetlands, with many paths featuring minimal elevation changes. Some trails are wider gravel roads, while others are more natural singletrack. The forest's interconnected paths allow for a diverse hiking experience.
Are there any easy, shorter loop trails suitable for families with young children?
Absolutely! For a pleasant and easy loop, consider the Winding Hills Park Loop. It's just over 4.5 km (2.8 miles) and offers a manageable distance for families with little ones.
Can we bring our dog on the family-friendly trails in Stewart State Forest?
Yes, Stewart State Forest is very dog-friendly! Many visitors enjoy bringing their canine companions along. Just remember to keep your dog on a leash and clean up after them to ensure a pleasant experience for everyone.
Are there any specific natural features or landmarks to look out for on these trails?
Stewart State Forest is home to diverse landscapes. A significant natural highlight is the Great Swamp, which features a unique boardwalk allowing visitors to experience this distinct ecosystem. You'll also encounter numerous ponds and a variety of wildlife, including white-tailed deer and various bird species, offering excellent opportunities for observation.
What is the best time of year to go hiking with family in Stewart State Forest?
Stewart State Forest is beautiful year-round, but spring and fall are particularly popular. Spring brings lush greenery and active wildlife, while fall offers stunning foliage. Summer is also great, though some trails can become overgrown. Winter hiking is possible, with opportunities for cross-country skiing and snowmobiling on wider paths.
Are there any longer, moderate family-friendly loops for a more extended adventure?
If you're looking for a longer, moderate loop, the Pine Root Trail & Ridge Road loop is a great option. It covers about 11.2 km (7 miles) and takes you through diverse woodlands and wetlands, offering a rewarding experience for active families.
What do other hikers enjoy most about the family-friendly trails in Stewart State Forest?
The area is highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the tranquil atmosphere, the variety of trails suitable for different skill levels, and the opportunities for wildlife spotting. The well-maintained paths and minimal elevation changes also make it a favorite for families.
Is there a trail that offers a good mix of open fields and wooded sections?
For a hike that combines open fields with wooded areas, consider the Orchard, Drakes, Windsor, and Camp Trail Loop. This moderate route is about 8.6 km (5.3 miles) and provides a lovely blend of landscapes, perfect for a varied family outing.
Are there any trails that are particularly good for birdwatching with kids?
Stewart State Forest is a fantastic spot for birdwatching. The diverse habitats, including wetlands and woodlands, attract a wide array of species. Keep an eye out for Ovenbirds, Blue-Winged Warblers, and Great Blue Herons, especially around the ponds and the Great Swamp boardwalk. Any of the trails that traverse these areas, such as the Drakes, White Cloud, Orchard, and Sara's Way Loop, offer good opportunities.
Most popular routes in Stewart State Forest
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