4.6
(6312)
7,137
hikers
Winding Hills Park Loop
01:13
4.63km
30m
Hiking
The Winding Hills Park Loop is an easy hiking route, covering 2.9 miles (4.6 km) with an elevation gain of 112 feet (34 metres). You can expect to complete this loop in about 1 hour and 12 minutes. This trail is located in Winding Hills County Park in Montgomery, Orange…
Last updated: March 7, 2026
Waypoints
Start point
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1.56 km
Diamond Lake
Highlight • Lake
Tip by
4.63 km
End point
Way Types & Surfaces
Way Types
3.52 km
1.05 km
< 100 m
Surfaces
3.52 km
730 m
351 m
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Elevation
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Weather
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Friday 8 May
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This route was planned by komoot.
Frequently Asked Questions
What is the terrain and difficulty like on the Winding Hills Park Loop?
This loop trail is generally considered easy, making it suitable for most hikers. You'll find winding paths through wooded areas with gentle, rolling hills and modest elevation changes. It's perfect for a leisurely stroll.
What natural features or landmarks will I see along the way?
The trail offers picturesque views, primarily centered around the tranquil 40-acre Diamond Lake. You'll also pass by a smaller four-acre pond, lush forests, and may spot old stone walls. Depending on the season, you might see wildflowers and various wildlife, including birds.
Where can I park for the Winding Hills Park Loop?
Parking is available at Winding Hills County Park in Montgomery, Orange County, New York. The trail starts directly from the park's main access points.
Is the Winding Hills Park Loop dog-friendly?
Yes, the park and its trails, including this loop, are known for being dog-friendly. Please ensure your dog is kept on a leash as per park regulations.
Are there any fees or permits required to access Winding Hills County Park?
The provided information does not indicate any specific fees or permits required for day use or hiking the trails at Winding Hills County Park. However, there are fees for camping at one of the 51 campsites.
What is the best time of year to hike this trail?
The trail is enjoyable year-round. Spring and summer offer lush greenery and wildflowers, while autumn provides vibrant fall foliage. Even in winter, when conditions allow, the park is open for activities like cross-country skiing and snowshoeing, offering a peaceful, snow-covered landscape.
Is the Winding Hills Park Loop suitable for families with children?
Absolutely! This trail is considered family-friendly due to its easy difficulty and scenic environment. The park also offers picnic areas and benches along the trails, making it a great outing for all ages.
Can I hike the Winding Hills Park Loop in winter?
Yes, you can hike the loop in winter. When conditions permit, the park also offers opportunities for winter activities such as ice skating, ice fishing, cross-country skiing, and snowshoeing, making it a versatile destination even in colder months.
What facilities are available at Winding Hills County Park?
Winding Hills County Park offers several amenities. You'll find picnic areas with tables and charcoal grills, benches along the trails, and opportunities for fishing in Diamond Lake or the smaller ponds. Paddle-sports are also allowed for car-top boats only. There are also 51 campsites available for overnight stays.
Are there any other activities available at Winding Hills County Park besides hiking?
Yes, Winding Hills County Park offers a wide range of activities. Besides hiking, visitors can enjoy birding, camping, fishing in Diamond Lake, and paddle-sports. In winter, when conditions are right, you can also go ice skating, ice fishing, cross-country skiing, and snowshoeing.