70
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10
rides
Road cycling in Bear Mountain State Forest, located in Cheshire County, offers routes through varied terrain. The region features significant elevation changes, with routes including substantial climbs and descents. Cyclists can expect to encounter forested areas and natural features such as ponds and river overlooks. The landscape provides a setting for both moderate and challenging road cycling experiences.
Last updated: July 9, 2026
14
riders
63.1km
03:07
660m
660m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
9
riders
94.3km
04:16
960m
960m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

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8
riders
53.1km
02:17
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
6
riders
55.5km
02:31
590m
590m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
6
riders
27.3km
01:18
350m
350m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Bear Mountain State Forest
A place of tranquility. Weatherhead Hollow pond is the ideal place to relax yourself and embrace some of the nature finest gifts: the soothing of the mind with smooth sound. The pond has a parking on the south end, which allows you to bring your non-motor sailing vehicle and float on its waters.
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A place of tranquility. Weatherhead Hollow pond is the ideal place to relax yourself and embrace some of nature's finest gifts: the soothing of the mind with smooth sound. The pond has parking on the south end, which allows you to bring your non-motor sailing vehicle and float on its waters. The views of the mountains and the forest are the ones you desire to find on your probably chilled bike touring adventure. Don't miss the opportunity to immortalize the scene.
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Feel yourself hovering over Sawyer Pond as you fly on Old Vernon Road. The brown fallen leaves of autumn make this place picture-worthy.
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Sawyer Pond lies on both sides of Old Vernon Road. This is a pretty spot to ride by because you are surrounded by water on both sides.
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Cushman Park, being right next to the Darwin Scott Wildlife Management Area, provides a green space for the public to enjoy. The park was donated back in 1908, and the adjacent Darwin Scott Wildlife Management Area provides 27.92 acres of explorable space. Cushman Park is an important part of the community, with local events and art displays happening here quite often.
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Trailhead with parking that lets you choose whether to take the paths that bring you east to Pisgah State Forest or west to Daniels Mountain. In the high season it can get busy, so make sure to get there early to get a parking spot.
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The Native Americans of the region used to call the West River "Wantastiquet" which means "waters of the lonely way”. The Wantastiquet Trail is connected to both the mountains and the West River. This path was an important link that connected Fort Drumner and the Green Mountains.
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You park near the marina at the southern end of Spring Tree Road in a large gravel lot by the river. From here you follow the river north on the road to where it quickly becomes a bike path.
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Road cycling in Bear Mountain State Park offers varied terrain, characterized by significant elevation changes. You'll encounter both substantial climbs and descents, with routes passing through forested areas and offering views of natural features like ponds and river overlooks. The region is known for its challenging ascents, such as the Perkins Memorial Drive, which features an average grade of 5.2% and sections up to 10%.
Yes, Bear Mountain State Park provides road cycling options for various ability levels. While many routes include significant climbs, you can find experiences ranging from moderate to difficult. For example, the Kilburn Trailhead – Sawyer Pond loop from Bear Mountain State Forest is rated moderate, while the West River overlook – Newfane Store loop from Brattleboro is considered difficult due to its substantial climbs.
The region is rich in natural beauty and historical sites. A major highlight is the Perkins Memorial Tower at the summit of Bear Mountain, offering sweeping 360-degree views of the Hudson River, Hudson Highlands, Harriman State Park, and even the distant New York City skyline on clear days. Other attractions include Hessian Lake, the Trailside Museums and Zoo (where the Appalachian Trail passes through), and the historic Bear Mountain Inn. While specific routes may not pass directly by all, they are within the park area.
The best time to road cycle in Bear Mountain State Park is generally from spring through autumn. The fall foliage offers particularly scenic rides. However, be prepared for varying seasonal conditions; some roads, like Perkins Memorial Drive, may be closed during winter months due to snow and ice. Always check local conditions before planning your ride.
Yes, several routes in the area are designed as loops. A popular moderate option is the Kilburn Trailhead – Sawyer Pond loop from Bear Mountain State Forest, which covers 39.2 miles. Another loop favored by local cyclists is the Weatherhead Hollow Pond – Cushman Park loop from Brattleboro, a 34.6-mile ride through varied terrain.
The area is highly rated by the komoot community, with an average score of 3.0 stars. Cyclists often praise the challenging climbs, the scenic forested landscapes, and the rewarding views, especially from high points like Perkins Memorial Tower. The variety of routes, from moderate to difficult, also contributes to its appeal.
While many routes in Bear Mountain State Park feature significant elevation changes and are rated moderate to difficult, some sections or shorter loops might be suitable for families with older, experienced children. The park also offers other family amenities like picnic groves and a merry-go-round, which could be combined with a shorter ride. Always check the specific route's difficulty and elevation profile to ensure it matches your family's capabilities.
The historic Bear Mountain Inn, located within the park, offers dining options and amenities. Additionally, depending on your specific route, you may find cafes or small stores in nearby towns like Brattleboro, which serve as starting points for several routes, including the Roadbike loop from Brattleboro.
Bear Mountain State Park offers various parking areas. Specific parking availability can vary depending on the trailhead or starting point of your chosen route. It's advisable to check the park's official website or specific route details for the most convenient and designated parking locations.
While direct public transport options specifically for cyclists with bikes might be limited to the immediate trailheads, Bear Mountain State Park is accessible via certain bus services from New York City, particularly during peak seasons. However, it's recommended to verify schedules and bike-carrying policies with the transport provider beforehand, as options can change. For detailed information on reaching the park, you may consult the official Bear Mountain State Park Wikipedia page for general access information.
Generally, specific permits are not required for road cycling on the paved roads within Bear Mountain State Park. However, always be aware of park regulations, especially concerning specific areas or events. It's good practice to check the official park website for any updated rules or temporary restrictions before your visit.
Both Bear Mountain State Park and its larger neighbor, Harriman State Park, offer excellent road cycling opportunities in the Hudson Highlands. Bear Mountain is particularly known for its iconic climb up Perkins Memorial Drive and panoramic views. Harriman State Park, while also very scenic and challenging, is larger and features a more extensive network of roads, often utilized for longer, more sustained rides and events like the Bear Mountain Classic road race. Both parks provide rugged mountain landscapes and significant elevation changes.


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