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.
Last updated: June 28, 2026
23
riders
80.8km
03:46
1,020m
1,020m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
7
riders
67.9km
03:27
940m
940m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Sign up for free
8
riders
36.3km
01:50
590m
590m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.5
(2)
5
riders
41.3km
02:02
550m
550m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
29.5km
01:33
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Popular around Windham
Unsure of the denomination but reminds me of the Old World Scandinavian churches
0
0
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
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.
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.
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.
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.
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.
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.
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.
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.
There are 19 road cycling routes available around Windham, New York, catering to various skill levels from easy to difficult.
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.
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.


Browse the best Road cycling routes in other regions.