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Routes
Road cycling routes
United States
New York
Greene County

Windham

The best road cycling routes around Windham

4.5

(2)

100

riders

19

rides

Road cycling around Windham, New York, offers a diverse landscape characterized by mountainous terrain and numerous back roads. The region features significant elevation gains, providing challenging climbs and scenic rural byways. Cyclists can explore forested areas, discover waterfalls, and enjoy views of the Catskill Mountains and the Hudson Valley. This area is known for its varied routes, catering to different skill levels.

Best road cycling routes around Windham

  • The most popular road cycling route is Coffee and bike shop – View of a wooden church loop from Town of Windham, a 50.2 miles (80.8 km) trail that takes 3 hours 46 minutes to complete. This difficult route features significant elevation gain through varied terrain.
  • Another top favourite among local road cyclists is Coffee and bike shop loop from Town of Windham, a difficult 40.5 miles (65.2 km) path. This route includes substantial elevation gain through varied terrain.
  • Local road cyclists also love the All Souls Church – Gothic Church loop from Hensonville, a 22.5 miles (36.3 km) trail leading through rural landscapes, often completed in about 1 hour 49 minutes.
  • Road cycling around Windham is defined by mountainous terrain, challenging climbs, and scenic rural byways. The network offers options for easy, moderate, and difficult routes.
  • The routes in Windham are highly rated by the komoot community with an average score of 4.5 stars from more than 2 reviews. More than 90 road cyclists have used komoot to explore Windham's varied terrain.

Last updated: June 28, 2026

23

riders

#1.

Coffee and bike shop – View of a wooden church loop from Windham

80.8km

03:46

1,020m

1,020m

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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Hard

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

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

Moderate

4.5

(2)

5

riders

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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Popular around Windham

Hiking around Windham

Cycling around Windham

Tips from the Community

Alex Tray
August 11, 2024, Downtown Tannersville

Lots of antiques and good food

0

0

Unsure of the denomination but reminds me of the Old World Scandinavian churches

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

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

Frequently Asked Questions

What kind of terrain can I expect when road cycling around Windham, NY?

Road cycling around Windham, New York, is characterized by its mountainous terrain, offering challenging climbs and scenic rural byways. You'll encounter significant elevation gains, forested areas, and varied landscapes, making it ideal for riders seeking a dynamic experience.

Are there routes suitable for beginners or those looking for an easier ride?

Yes, while Windham is known for its challenging climbs, the network offers options for various skill levels. There is at least one easy route available, and many moderate routes, ensuring that cyclists of different abilities can find a suitable ride. For example, the Coffee and bike shop – View of a wooden church loop from Town of Windham is a moderate option with manageable climbs.

What are some of the longer road cycling routes in the Windham area?

For those seeking longer rides, Windham offers several routes over 60 kilometers. The Coffee and bike shop loop from Town of Windham is a challenging 65.2 km path with substantial elevation gain, while the Coffee and bike shop – View of a wooden church loop from Town of Windham covers 63.7 km with moderate climbs.

Can I find circular road cycling routes in Windham, NY?

Absolutely. Many of the routes around Windham are designed as loops, allowing you to start and finish in the same location. Examples include the All Souls Church – Gothic Church loop from Hensonville and the Five State Lookout loop from Brooksburg Unit.

What kind of natural features or landmarks can I see along the road cycling routes?

The Windham, NY, Catskills region offers diverse natural beauty. You can expect to see waterfalls, glimpses of the White Mountains from certain viewpoints, and ride through lush forests and rural landscapes. Some routes also feature views of local architecture, such as the All Souls Church – Gothic Church loop from Hensonville.

Are there any challenging routes for experienced road cyclists?

Yes, Windham is well-regarded for its challenging road cycling. Routes like the Coffee and bike shop loop from Town of Windham are classified as difficult, featuring significant elevation gains and demanding sections. The region is known for its 'sheer number of back roads' and variations for endless exploration, including renowned climbs.

What do other cyclists say about road cycling in Windham?

The road cycling routes in Windham are highly rated by the komoot community, with an average score of 4.5 stars. Cyclists often praise the mountainous terrain, challenging climbs, and scenic rural byways that define the area's riding experience.

Are there places to stop for coffee or bike services along the routes?

Yes, some route names, such as the Coffee and bike shop – View of a wooden church loop from Town of Windham, suggest that coffee shops and bike services are accessible in or near the starting points of these routes, particularly in the Town of Windham.

How many road cycling routes are available in the Windham, NY area?

There are 19 road cycling routes available around Windham, New York, catering to various skill levels from easy to difficult.

What is the typical elevation gain on road cycling routes in Windham, NY?

The elevation gain varies significantly depending on the route. For example, a moderate route like the Coffee and bike shop – View of a wooden church loop from Town of Windham has an elevation gain of around 390 meters, while a difficult route such as the Coffee and bike shop loop from Town of Windham features over 916 meters of climbing.

Is Windham, NY, considered a good destination for road cycling?

Yes, Windham in the Catskills region of New York is considered a renowned destination for road cycling, often referred to as the 'Adventure Capital of NY' for its extensive network of back roads, challenging climbs, and scenic routes.

Most popular routes around Windham

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