The best walks and hikes around Ridgebury
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178
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34
hikes
Hikes around Ridgebury explore a landscape of rolling wooded hills, glacial erratics, and dense forests. The region is characterized by numerous streams, wetlands, and meadows, often framed by historic stone walls. The trails navigate a variety of habitats, offering routes with both gentle and moderate elevation changes.
Best hiking trails around Ridgebury
- The most popular hiking route is the Bennett's Pond via Ives Trail Greenway loop — Bennett's Pond State Park, a 3.4 mile (5.5 km) trail that takes…
Last updated: June 28, 2026
5.0
(2)
11
hikers
12.7km
03:35
260m
280m
Embark on the Hemlock Hills and Pine Mountain Trail for a moderate hike spanning 7.9 miles (12.7 km), featuring a total elevation gain of 844 feet (257 metres). You can…
4.0
(1)
7
hikers
6.15km
01:42
110m
110m
The Bailey Mountain trail in Westchester County, New York, offers a refreshing escape into nature with its gentle terrain and peaceful atmosphere. You'll wander through a pleasant mix of forest…
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1
hikers
2.33km
00:38
50m
10m
The White Trail offers a delightful, easy hike, perfect for a quick nature fix. You'll wander through peaceful wooded sections, eventually reaching the tranquil Trail at Lake Naraneka, providing a…
1
hikers
1.76km
00:28
20m
20m
Step into the tranquil embrace of Farringtons Woods Trail, an easy 1.1-mile (1.8 km) hike that winds through a lush green forest near the New York-Connecticut border. This short route,…
9.48km
02:40
180m
220m
Hike the moderate 5.9-mile Green Blaze and Yellow Blaze Loop in Bennett's Pond State Park, featuring varied terrain and Bennett's Pond.
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Tips from the Community
An offshoot of the trails leads to a swing with a view of the lake! There are residences around the lake, and you can sometimes see the residents boating, fishing, or swimming.
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This pond is part of the headwaters of the Saugatuck River, ultimately providing drinking water to lower Fairfield County. The trail circles the entire pond. We were there in August, and saw some swans! But also lots of mosquitoes. And there wasn't really any good spot to rest for a picnic either. The trail around the pond is very narrow and the vegetation is dense around the trail, at least in the summer.
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This is all that's left of a cabin built by Charles and Moss Ives in 1903 (Charles Ives was a well-known composer). Here is a picture of what the cabin originally looked like: https://vizettes.com/trailmaps/fcnemba-trailmaps/bennettspond/bp-images/Ives_Shanty.jpg You can see from the picture that the cabin had an incredible view down the mountain, which may have inspired Ives' work.
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Pine Mountain viewpoint. Not the summit, but an excellent view nonetheless. We saw evidence of someone's firepit at the viewpoint, but it's likely NOT an authorized firepit. This is NOT a place to build a fire! The clearing for the viewpoint is wayy too close to the pines!
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Once you hit the upper ridge of Pine Mountain, you start to get sporadic views through the trees. This is a great final rest point if you are still pushing uphill. On a clear day, you can see up to 5 rows of rolling hills in the distance.
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The Lake Windwing area has some nice trails that are fun in the summer and covered with snow in the winter. The lake itself is nice to visit while on a ride. There is a parking lot at the end of North Shore Drive to access the area.
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In summer, it is a great place for hiking, and in winter, when the lake is covered with ice, it is great for ice skating.
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Very nice place with a wonderful view. Just right for a short break.
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Frequently Asked Questions
Are there any easy, family-friendly hikes in the Ridgebury area?
Yes, the region offers several gentle walks suitable for families. The landscape around Ridgebury includes many trails with minimal elevation change. A great example is the Bennett's Pond via Ives Trail Greenway loop, which is an easy path around a scenic pond. The Peterson Gorge/Ridgebury Slope trail is also ideal for family explorations, with a path along a stream and several bridge crossings.
Can I bring my dog on the hiking trails around Ridgebury?
Most trails in the state parks and preserves around Ridgebury are dog-friendly, provided your dog is kept on a leash. Parks like Bennett's Pond State Park and Hemlock Hills are popular spots for dog walkers. Always check the specific regulations for the park you plan to visit before you go.
What are some popular places to hike near Ridgebury?
Besides the main state parks, local hikers enjoy several other spots. Hemlock Hills is a popular choice, known for its challenging trails and great views. For a mix of history and nature, Mine Hill Preserve is a highly-regarded option, featuring old mineshafts and beautiful scenery. The Ives Trail is another favorite, offering a 20-mile path through heavily wooded areas.
Are there any circular or loop trails suitable for trail running?
Yes, Ridgebury has several loop trails perfect for running. The Park Loop in Seth Low Pierrepont State Park Preserve offers a moderately challenging 4.5-mile circuit with varied terrain. For a longer run with significant elevation, the Hearthstone Castle via Ives Trail Greenway loop is a great option, covering over 7 miles.
What kind of scenery can I expect on the trails?
The hiking trails around Ridgebury showcase a classic New England landscape. You'll walk through rolling wooded hills, dense forests with large glacial boulders, and open meadows. Many trails are framed by historic stone walls and follow picturesque streams and wetlands.
Are there any hikes with good viewpoints?
Yes, you can find rewarding views on several trails. The Ives Cabin Chimney Ruin – Great Viewpoint loop from Hemlock Hills is specifically known for its scenic overlooks. Hemlock Hills is a popular spot for hikers seeking great views from its higher elevations.
How many hiking trails are there around Ridgebury?
There are over 20 designated hiking routes to explore around Ridgebury on komoot. These range from easy, short walks to more challenging moderate trails, ensuring there's a path for every fitness level.
What do other hikers think of the trails in Ridgebury?
The area is highly rated by the komoot community, with an average score of 4.8 stars. Hikers often praise the region's beautiful, well-maintained woodlands, the variety of trails, and the scenic beauty of the ponds and streams.
Are there any waterfalls on the hiking trails?
While the immediate Ridgebury area is known more for its streams and wetlands, you can find waterfalls nearby. A short drive to Rocky Glen State Park Scenic Reserve will reward you with a beautiful waterfall over a dam, which is a highlight of the park's main trail.
What is the best time of year to hike in Ridgebury?
Hiking in Ridgebury is enjoyable year-round, but spring and autumn are particularly special. In spring, the forests come alive with wildflowers like trout lily and jack-in-the-pulpit. Autumn offers spectacular fall foliage, creating a colorful backdrop for your hike.
What should I pack for a day hike in the area?
For a day hike, you should bring sturdy hiking shoes, as trails can be rocky and uneven. Pack plenty of water and some snacks. A map or a GPS device is recommended, along with insect repellent, especially during warmer months. Due to the presence of poison ivy in some areas like Hemlock Hills, wearing long pants is a good idea.
Where can I park to access the trails?
Most state parks and preserves, such as Bennett's Pond State Park and Seth Low Pierrepont State Park Preserve, have designated parking areas near the trailheads. For other popular spots like Hemlock Hills and the Pine Mountain Trail Head, you will also find dedicated parking. It's always a good idea to arrive early on weekends as lots can fill up.
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