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Greene County

Windham-Blackhead Range Wilderness

The best road cycling routes in Windham-Blackhead Range Wilderness

4.5

(4)

295

riders

38

rides

Road cycling routes in Windham-Blackhead Range Wilderness traverse a mountainous landscape characterized by dense forests and significant elevation changes. This region features prominent peaks over 3,000 feet, providing challenging terrain for road cyclists. The area's roads often include sustained climbs and descents, with some routes reaching over 1,200 meters of elevation gain. The wilderness offers a mix of well-paved roads and some unpaved segments on longer routes.

Best road cycling routes in Windham-Blackhead Range Wilderness

  • The most popular road cycling…

Last updated: July 12, 2026

2

riders

#1.

All Souls Church – Gothic Church loop from Katydid Creek Unit

20.4km

01:12

430m

430m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Tips from the Community

Alex Tray
August 11, 2024, Downtown Tannersville

Lots of antiques and good food

0

0

Had a feed stop here but also had drinks

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0

Alex Tray
August 11, 2024, Gothic Church

Has a great view of the valley

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0

This lake and the park where it's located are perfect for enjoying a nice time on the bike, especially if you ride with the family. When it's hot, it's a great place to take a dip.

1

0

Javi Jaavii
February 10, 2024, All Souls Church

Very close to the Mountain Top Arboretum, alongside the road, you'll find this beautiful stone church built in the late 19th century. Although originally a small chapel in the Gothic Revival style, it was later enlarged. It is listed on the National Register of Historic Places since 1993.

1

0

Buck R-T
February 13, 2023, Five State Lookout

On a clear day, you can see VT, MA, CT

0

0

Frequently Asked Questions

How many road cycling routes are available in the Windham-Blackhead Range Wilderness?

There are over 30 road cycling routes in the Windham-Blackhead Range Wilderness, offering a diverse range of experiences. These include 2 easy routes, 24 moderate routes, and 10 difficult routes, catering to various fitness levels.

What kind of terrain and elevation can I expect on road cycling routes in this region?

The Windham-Blackhead Range Wilderness is characterized by mountainous terrain with significant elevation changes. You can expect sustained climbs and descents, with some routes featuring over 1,200 meters of elevation gain. While many roads are well-paved, some longer or more challenging routes may include unpaved segments.

Are there any particularly challenging road cycling routes for experienced riders?

Yes, for experienced riders seeking a challenge, routes like the Gothic Church – Downtown Tannersville loop from East Jewett offer a difficult 93 km ride with over 1,200 meters of elevation gain. Another demanding option is the Kaaterskill Falls Climb – Gothic Church loop from Barnum Road Unit, which includes a substantial climb over its 66 km length.

What are some scenic viewpoints or landmarks I can see while road cycling in the Windham-Blackhead Range Wilderness?

The region offers numerous scenic vistas. You can find incredible views along the Escarpment Trail, which coincides with portions of the Long Path. Specific viewpoints include North Point, Burnt Knob, and Acra Point. The Windham High Peak Overlook also provides spectacular views. Additionally, the majestic peaks like Windham High Peak, Black Dome, and Blackhead Mountain are visible for many miles.

Are there any road cycling routes that pass by natural water features like waterfalls?

While not directly on a road cycling route, the iconic Kaaterskill Falls is a significant natural feature in the area. It is accessible via a 2.3-mile section of the Escarpment Trail, offering stunning views from a platform. Cyclists can plan a ride that brings them close to trailheads leading to such features.

What do other road cyclists say about their experience in the Windham-Blackhead Range Wilderness?

The road cycling routes in Windham-Blackhead Range Wilderness are highly rated by the komoot community, with an average score of 4.5 stars. Cyclists often praise the challenging mountainous terrain, the dense forests, and the significant elevation changes that make for a rewarding ride.

Are there any moderate road cycling routes suitable for those with good fitness but not seeking extreme challenges?

Yes, there are many moderate options. The Coffee and bike shop loop from East Jewett is a popular moderate route, covering 50.8 km through forested areas. Another good choice is the All Souls Church – Gothic Church loop from Village of Tannersville, a 42.9 km ride with manageable elevation.

What is the best season for road cycling in the Windham-Blackhead Range Wilderness?

The best seasons for road cycling are typically spring, summer, and fall. During these months, the weather is generally more favorable, and the natural scenery, from lush green forests to vibrant fall foliage, enhances the riding experience. Winter conditions can bring snow and ice, making road cycling challenging or impossible on many routes.

Are there any easy or beginner-friendly road cycling routes in the area?

While many routes feature significant elevation, there are a couple of easier options. For instance, the All Souls Church – Gothic Church loop from Katydid Creek Unit is a moderate route at 20.3 km with 434 meters of elevation, which could be a good starting point for those building fitness or looking for a shorter ride.

Where can I find parking for road cycling routes in the Windham-Blackhead Range Wilderness?

Parking availability varies by trailhead and starting point. Many routes, such as those starting from East Jewett or Barnum Road Unit, will have designated parking areas nearby. It's advisable to check specific route details on komoot for parking information related to your chosen starting point.

Can I find cafes or bike shops along the road cycling routes?

Yes, some routes are designed to incorporate amenities. For example, the Coffee and bike shop loop from East Jewett specifically highlights opportunities to stop at local cafes and bike shops, providing convenient breaks and services during your ride.

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