4.6
(16)
206
riders
29
rides
Touring cycling around Town of Highlands offers routes through the southern Appalachian Mountains and the Nantahala National Forest. The region is characterized by varied terrain, including scenic mountain roads and the unique temperate rainforest environment. Cyclists can explore routes with significant elevation changes, passing by numerous waterfalls and enjoying lush, green scenery. This area provides a diverse landscape for both challenging rides and more moderate explorations.
Last updated: May 1, 2026
5.0
(1)
4
riders
47.7km
03:58
860m
860m
Embark on the Candlewood Hill Loop, a difficult touring cycling route that challenges you with varied terrain, including gravel and woods roads, and unpaved sections like Sunken Mine Road. Over…
5.0
(1)
15
riders
13.1km
01:03
340m
340m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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4.0
(1)
16
riders
17.5km
01:08
150m
150m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
10
riders
39.1km
03:15
800m
800m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
10
riders
24.2km
01:48
530m
530m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Bear Mountain, located in the Hudson Highlands of southeastern New York, is one of the most notable landmarks on the Appalachian Trail in the state. The AT crosses directly over the summit, which stands at 1,305 feet, which is not especially high, but it is a historically and symbolically significant summit; it’s home to the oldest continuously maintained section of the Appalachian Trail, built in 1923, and features wide stone steps and paved walkways constructed by trail crews and the Civilian Conservation Corps. For many hikers, Bear Mountain is also the site of the lowest elevation point on the AT, near the Hudson River just before the climb. From the top, you get sweeping views of the Hudson Valley, and the surrounding Bear Mountain State Park includes a lake, picnic areas, the Trailside Museum and Zoo (which the AT technically passes through), and access to nearby Perkins Memorial Tower. It’s a popular day hike, so don’t be surprised to share the trail with weekend crowds, especially in fall.
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Bear Mountain peaks at just under 1,300 feet in elevation over a 4.5-mile stretch of picturesque paved road. Although it may seem small in comparison to some of the world’s renowned climbs, it makes up for this with stunning views of the Hudson Highlands.
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The road makes a loop around the summit of Bear Mountain with the Perkins Memorial Tower at its center. From the top you get sweeping views south across the Hudson, Harriman State Park, and the route taken by the Appalachian Trail.
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Highland Falls, situated in Orange County, New York, is a quaint village neighboring the renowned United States Military Academy at West Point. With a population of around 3,900, the village boasts a rich history intertwined with the academy's legacy. Its scenic location along the Hudson River and proximity to the Hudson Highlands State Park offer residents and visitors ample opportunities for outdoor recreation. With plenty of local shops, restaurants, and annual events, Highland Falls is a great spot for residents and visitors alike to relax after a long ride or hike.
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Highland Falls, once Buttermilk Falls, transformed into a village in Orange County. Officially incorporated in 1906, it boasts a population of 3,684 as of 2020. Recognized for its suburban allure, the town is esteemed as one of the best places to live in New York, featuring numerous bars, restaurants, and coffee shops.
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Popular hiking destination not far from New York City with great views
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The unobstructed 360 views are worth the extra 70 feet up the tower when it's open
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No views here as they are blocked by the trees, but it's the tallest natural point on the mountain as the geodesic marker indicates
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There are 28 touring cycling routes around the Town of Highlands. These routes offer a diverse range of experiences, from moderate paths to challenging climbs through the Appalachian Mountains.
The Town of Highlands, nestled in the southern Appalachian Mountains, offers varied terrain for touring cyclists. You can expect scenic mountain roads with significant elevation changes, lush landscapes due to its temperate rainforest environment, and routes through the dense Nantahala National Forest. The area provides a mix of paved and well-maintained unpaved roads.
Yes, there are routes suitable for less experienced cyclists. For example, the Highland Falls loop from Village of Highland Falls is a moderate 10.9-mile (17.5 km) trail that leads through varied local landscapes, often completed in about 1 hour 10 minutes. This route offers a more relaxed exploration of the area.
For experienced cyclists seeking a challenge, the Town of Highlands offers several difficult routes with significant elevation gains. A notable option is the Candlewood Hill Loop, a 29.6-mile (47.7 km) trail that takes approximately 4 hours to complete and features substantial climbing through mountain terrain.
Absolutely. Many routes in the Town of Highlands provide breathtaking mountain views and pass by natural attractions. The region is renowned for its numerous waterfalls, such as Bridal Veil Falls, Cullasaja Falls, Dry Falls, and Glen Falls. You can also find routes with panoramic vistas from points like Sunset Rock and Whiteside Mountain. For a route with a specific viewpoint, consider the View from Bear Mountain Summit – Perkins Memorial Tower loop from Bear Mountain State Park, which offers scenic views from a mountain summit.
The touring cycling routes in the Town of Highlands are highly rated by the komoot community, with an average score of 4.4 stars from 18 reviews. Nearly 200 touring cyclists have explored the area using komoot, often praising the diverse terrain, challenging mountain roads, and the immersive experience of the Nantahala National Forest.
Yes, the Town of Highlands offers several circular routes for touring cyclists. An example is the Indian Brook Road - gravel – Sunken Mine Road loop from Cold Spring, a difficult 39.1-mile (63 km) route that provides a comprehensive tour of varied landscapes.
Beyond the routes themselves, the area around the Town of Highlands is rich with natural features. You can explore various lakes such as Hessian Lake and Lake Tiorati. There are also notable viewpoints like South Beacon Mountain and Firetower, offering expansive vistas of the surrounding Appalachian landscape.
Given its temperate rainforest environment, the Town of Highlands experiences lush, green scenery throughout much of the year. While cycling is possible for many months, spring and fall often offer the most pleasant temperatures and vibrant natural beauty, with fewer extremes in weather. However, the region receives over 80 inches of rain annually, so be prepared for potential wet conditions at any time.
Many routes within the Nantahala National Forest and surrounding areas will immerse you in the temperate rainforest environment. The constant moisture fosters incredible biodiversity and lush, green scenery. Routes that follow river valleys or pass by waterfalls, such as those near Cullasaja Falls or Glen Falls, will particularly highlight this unique ecological feature.
Yes, in addition to the route from Bear Mountain State Park, you can also access the scenic views from Bear Mountain Summit via a different starting point. Consider the View from Bear Mountain Summit – Perkins Memorial Tower loop from Manitou, a difficult 24.2-mile (39 km) route that provides another perspective of this popular area.


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