4.7
(13)
1,151
riders
40
rides
Road cycling routes around Hillcrest offer a diverse landscape, characterized by rolling hills and varied terrain suitable for different skill levels. The region features a mix of open roads and more secluded paths, providing opportunities for both challenging climbs and scenic, flatter sections. Cyclists can expect to encounter a blend of natural features, including wooded areas and open stretches, as they navigate the routes. The topography supports a range of road cycling experiences, from endurance rides to shorter, more accessible…
Last updated: May 14, 2026
423
riders
133km
05:47
1,010m
1,010m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
65
riders
72.5km
03:11
560m
560m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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29
riders
39.4km
01:37
260m
260m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
22
riders
148km
07:36
2,000m
2,000m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
21
riders
58.1km
02:42
660m
660m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Hillcrest
This is a nice uphill challenge. Just shift to a low gear. You can do it.
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Piermont is a quaint, small town along the Hudson River. There are several restaurants, cafés, and shops in the town, so it is a good place for a break if you are hiking the Long Path.
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This road is a treat whether you're heading up or downhill. Lake Sebago is gorgeous as well and a great place to have a water break after the climb.
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Originally a small pond, Lake Welch was increased to its current size when a dam was built in 1942. It boasts the largest beach in Harriman State Park as well as multiple picnic and bbq areas.
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Little Long Pond is beautiful any time of year, but if you happen to be riding along Kanawauke Road during the fall color season you'll be in for a real treat!
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Many people enjoy coming here for a peaceful break. You might see families having picnics by the water or people simply sitting on benches, enjoying the quiet. The pond and the pathway are good for seeing local wildlife. Besides ducks, you might spot turtles sunning themselves or different kinds of birds flying overhead.
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There are over 40 road cycling routes around Hillcrest, offering a diverse range of experiences. These include 14 easy routes, 19 moderate routes, and 10 challenging routes, catering to various skill levels.
Road cycling around Hillcrest is characterized by rolling hills, open roads, and wooded sections. You'll find a mix of challenging climbs and scenic, flatter sections, providing varied topography for different types of rides.
Yes, Hillcrest offers several easy road cycling routes. One popular option is the Ridgewood – Wild Duck Pond loop from Monsey, which is 24.5 miles (39.4 km) long and leads through varied landscapes, often completed in about 1 hour 37 minutes.
For those seeking challenging climbs, the Hillcrest area has several options. A notable difficult route is the Bear Mountain Climb – View from Bear Mountain Summit loop from Nanuet, a 57.0 miles (91.8 km) path known for its substantial elevation gains and panoramic views.
The road cycling routes in Hillcrest are highly rated by the komoot community, with an average score of 4.2 stars from over 11 reviews. Cyclists often praise the varied terrain, from rolling hills to wooded sections, and the options available for different ability levels.
Many routes offer scenic views, especially those with elevation. For instance, the Bear Mountain Climb – View from Bear Mountain Summit loop from Nanuet provides panoramic vistas. Additionally, routes often pass by natural features like Pine Meadow Lake and the Hudson River Waterfront Trail at Nyack Beach State Park.
Yes, many road cycling routes in Hillcrest are designed as loops. Examples include the Hudson River Greenway – The Little Red Lighthouse loop from Nanuet and the Ridgewood – Wild Duck Pond loop from Monsey, offering convenient starting and ending points.
Beyond the routes themselves, you can explore several interesting spots. The Hudson River Waterfront Trail at Nyack Beach State Park offers beautiful views, and you might even pass by Big Hill. For a break, consider stopping at the Boxer Donut & Espresso Bar.
Absolutely. Several road cycling routes in the Hillcrest area offer views of or pass near beautiful lakes. You can find routes that go by Pine Meadow Lake, Rockland Lake South, and Third Reservoir, providing refreshing scenery during your ride.
A popular moderate route is the Little Long Pond – Lake Welch Beach loop from Spring Valley. This route covers 58.2 miles (93.7 km) and typically takes around 2 hours 40 minutes, offering a balanced challenge with significant elevation.
For longer endurance rides, the Hudson River Greenway – The Little Red Lighthouse loop from Nanuet is an excellent choice. It spans 82.3 miles (132.5 km) and features significant elevation gain, typically requiring about 5 hours 46 minutes to complete.


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