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Hiking in Winding Hills County Park: trails, map and practical info

Hudson Valley • New York

4.7 Appreciated by 2 hikers
François Dumaine
By François DumaineContributor since 2022Updated 29/05/2026
Difficulty
Easy
Distance
3 km
Elevation
50 ft
Duration
1h00

Explore 3.2 km of rolling Hudson Valley terrain in Montgomery, New York—a quieter alternative to crowded regional destinations. This easy, 1-hour loop winds through hardwood forests and hugs a serene lakeside trail, offering consistent water views and wildlife sightings without the crowds.

Recommended for :
Beginners

Ready to explore Winding Hills County Park? Here's everything you need to know before you go!

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Trail description

Description

Winding Hills County Park sprawls across 500 acres of classic Hudson Valley terrain in Montgomery, New York, offering hikers a genuine taste of the region's diverse landscapes. The park combines rolling forested hills with serene lakefront areas, creating a varied outdoor experience that changes dramatically with the seasons. Unlike some of the more crowded destinations in the Hudson Valley, Winding Hills maintains a quieter atmosphere while still providing well-maintained facilities and trail systems.

The park's trail network winds through dense hardwood forests dominated by oak, maple, and hickory trees, which create spectacular displays during fall foliage season. These same forests provide excellent wildlife viewing opportunities year-round, with frequent sightings of white-tailed deer, wild turkeys, and various songbird species. The terrain varies from gentle slopes perfect for families to more challenging climbs that reward hikers with elevated views of the surrounding valley.

Trail System and Terrain

The park's trail system accommodates hikers of all experience levels, with routes ranging from easy lakeside walks to more demanding hill climbs. The well-maintained paths are clearly marked and regularly maintained, making navigation straightforward even for first-time visitors. Most trails can be completed in 2 to 3 hours, though the modular design allows for shorter or longer outings depending on your preferences.

The standout route is the Lakeside Trail, which hugs the shoreline of the park's central lake and provides consistently beautiful water views. This trail features relatively flat terrain with occasional gentle rises, making it accessible for most fitness levels. The path includes several strategically placed benches and clearings that serve as perfect spots for rest breaks or quiet contemplation. The lake itself reflects the surrounding hills and forest canopy, creating particularly striking scenes during early morning or late afternoon visits.

For hikers seeking more elevation gain, the park's hill trails offer modest climbs through dense forest cover. While the elevation gain of approximately 50 meters isn't extreme, the rolling nature of the terrain provides a good workout and varied perspectives of the landscape. These higher trails offer glimpses through the tree canopy toward the broader Hudson Valley, especially during winter months when the leaves have fallen.

Seasonal Experiences

Winding Hills County Park operates year-round, with each season bringing distinct advantages for outdoor enthusiasts. Spring hiking reveals wildflowers emerging along the forest floor and migrating birds returning to the area. Summer provides full canopy cover that keeps trails relatively cool even on hot days, while the lake areas offer refreshing breezes.

Fall transforms the park into a showcase of Hudson Valley foliage, with the mixed hardwood forests displaying vibrant reds, oranges, and yellows. This season draws the most visitors, particularly during peak foliage weekends. Winter hiking offers a completely different perspective, with bare trees revealing long-distance views and the lake sometimes freezing over to create stark, beautiful landscapes.

Beyond the Trails

While hiking forms the core attraction, Winding Hills County Park supports various other outdoor activities. The central lake is stocked with bass and other fish species, making it a legitimate destination for anglers. Fishing access points are scattered around the shoreline, with some accessible directly from the trail system.

The park includes designated picnic areas that work well for families or groups planning extended visits. These areas feature tables and basic facilities, positioned to take advantage of lake views or forest settings. Birdwatching opportunities abound throughout the park, with the varied habitats supporting both forest species and waterfowl around the lake areas.

Access and Location

Located in Montgomery, New York, Winding Hills County Park sits in the heart of the Hudson Valley region, making it easily accessible from various points throughout the area. The park's location provides convenient access while maintaining the feeling of being immersed in nature once you're on the trails.

The surrounding region offers additional attractions for visitors planning extended stays. The Orange County Firefighters Museum provides insight into local history and makes an interesting complement to outdoor activities. Historic sites like Bull Stone House offer glimpses into the area's colonial past, while modern amenities like Nervani Beauty spa provide relaxation options after active days outdoors.

For those planning overnight visits, Middletown offers various hotel accommodations within reasonable driving distance of the park. The area maintains good cell coverage from major carriers including T-Mobile, Verizon, and AT&T, ensuring connectivity for navigation and emergency purposes.

Regional Water Features

The park's location within the broader Hudson Valley water system adds to its appeal for water-oriented activities. The Wallkill River meanders through the region, providing opportunities for kayaking and canoeing enthusiasts who want to extend their outdoor experience beyond hiking. These river sections offer different perspectives on the valley's landscapes and wildlife.

Diamond Lake, another nearby water feature, provides additional options for those drawn to lakefront activities. The combination of these water resources with the park's own lake creates multiple options for visitors interested in both land and water-based recreation.

Whether you're visiting during a busy holiday weekend like Labor Day or seeking solitude during quieter weekday periods, Winding Hills County Park delivers a solid Hudson Valley hiking experience without the crowds found at some better-known destinations. The combination of accessible trails, diverse terrain, and additional recreational opportunities makes it a practical choice for both local residents and visitors exploring the broader region.

Recommended gear for this trail

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Elixir Tour Mid WP
Salomon
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Wide Mouth 1L
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Trail Ergo Cork
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69.99 $
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Actik Core 625
Petzl
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Ready to go?

Everything you need to know before you go

Where?

Address
1847 NY-17K, Montgomery, NY 12549, USA
GPS coordinates
41.5368919, -74.2738101
Phone
(845) 457-4918

Starting Point

The easiest way to get to the start of the trails at the winding hills county park in New York is to take exit 16 from the New York State Thruway and then follow the signs to the park.

When?

Opening hours
Monday: 7:00 AM – 8:00 PMTuesday: 7:00 AM – 8:00 PMWednesday: 7:00 AM – 8:00 PMThursday: 7:00 AM – 8:00 PMFriday: 7:00 AM – 8:00 PMSaturday: 7:00 AM – 8:00 PMSunday: 7:00 AM – 8:00 PM
Varies by season
Best season
Fall
Spectacular colors
Best time
Early morning
Less crowded
Weather (next days)
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How much?

Entry fees
Adult
Not available
Child
What to bring?
Gear
Download the PDF checklist
Water & food
2L minimum
No water point on the trail
Bring energy snacks for a 4h+ hike
Good to know
Park rules
No dogs
Safety
Download the GPX before you go
Limited cellular coverage on the trail
Slippery after rain
Be careful on rocky sections
In an emergency
Emergency
911
Parking GPS
41.5368919, -74.2738101
Center
(845) 457-4918

Hikers' opinions

4.7
1 Reviews
PV
Park Visitor
Jan 15, 2024
Great hiking experience at Winding Hills County Park! The 50m elevation gain provides just enough challenge for a moderate workout without being too strenuous. Took us about 2.5 hours to complete the trails at a leisurely pace, enjoying the Hudson Valley scenery. Note that parking isn't free and dogs aren't allowed, so plan accordingly. The trails are well-maintained and offer beautiful views of the surrounding hills.

FAQ - Frequently asked questions

Everything you need to know
Easy
50.00
Monday: 7:00 AM – 8:00 PMTuesday: 7:00 AM – 8:00 PMWednesday: 7:00 AM – 8:00 PMThursday: 7:00 AM – 8:00 PMFriday: 7:00 AM – 8:00 PMSaturday: 7:00 AM – 8:00 PMSunday: 7:00 AM – 8:00 PM
1h00
No
No
Yes, the Winding Hills County Park trail is rated as Easy, making it suitable for beginners and those new to hiking. With a distance of 3.2 km and an elevation gain of only 50 m, it's an accessible option for most fitness levels.
The Winding Hills County Park trail takes approximately 1h00 to complete. This timing is based on the 3.2 km distance and 50 m elevation gain on an Easy-rated path.
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Update : June 2026