4.6
(25)
468
riders
66
rides
Touring cycling in Berkshire County offers routes through a landscape characterized by rolling hills, tranquil valleys, and lush forests in western Massachusetts. The region features mountain views from the Taconic Range and the Housatonic River Valley, providing diverse terrain for cyclists. Numerous lakes and rivers, such as Onota Lake and the Housatonic River, add to the scenic beauty of many routes. Forests and parks like Pittsfield State Forest also contain multi-use trails.
Last updated: April 24, 2026
5.0
(9)
103
riders
43.8km
02:30
140m
140m
Embark on a touring bicycle adventure along the Ashuwillticook Rail Trail, a moderate 27.2 miles (43.8 km) route that follows a former railroad corridor. You will enjoy a smooth, level ride, gaining 453 feet (138 metres) in elevation over approximately 2 hours and 29 minutes. As you cycle, the trail winds through lush forested areas and wetlands, offering serene views of the Hoosic River Valley. Keep an eye out for glimpses of Mount Greylock in the distance and the tranquil waters of the Cheshire Reservoir. This path provides a peaceful escape into nature, perfect for a relaxed ride.
Planning your trip to the Ashuwillticook Rail Trail is straightforward, with several convenient access points. You will find seasonal restrooms available at key trailheads, including the Adams Visitor Center and the historic Boston & Albany Railroad Station in Cheshire. The route is well-maintained, featuring benches and picnic tables along the way for rest stops. This trail is also wheelchair accessible and welcomes dogs, making it a versatile option for many visitors.
The Ashuwillticook Rail Trail is notable for its transformation from a bustling railroad line into a scenic recreational path. This unique history allows you to traverse the landscape on a level grade, offering an intimate perspective of the Berkshire region's natural beauty. The wetlands and forested sections provide excellent opportunities for wildlife spotting, from various bird species to turtles. In autumn, the changing leaves create a particularly vibrant and memorable backdrop for your ride.
5.0
(4)
68
riders
42.0km
02:30
270m
270m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(1)
39
riders
32.0km
01:51
130m
130m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
26
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
14
riders
61.9km
04:10
1,000m
1,000m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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This is the most beautiful rail trail in Massachusetts hands down.
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A great monument with a magnificent view once you have conquered the stairs. Tip: hike to the summit!
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Converted from an old railroad track, the Ashuwillticook Rail Trail is now a 10 foot wide, 14.2 mile, paved multi use trail meandering along the Cheshire Reservoir while offering sublime views of Mt. Greylock.
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Located just north of Adams, the Ashuwillticook Rail Trail Head sets a lovely tone for the rest of your ride along the trail, perfectly smooth and easy to use for families.
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Fitch Overlook is located on Notch Road at an elevation of 2,850 feet, just below Mount Fitch itself, at Mount Greylock State Reservation. It is not a large overlook by any means, but it has great views out over towards Mount Prospect and Stony Ledge.
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Here's the Trail Head of the Ashuwillticook Rail Trail. The trail is perfectly smooth and easy to use for families.
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This is the highest point in Massachusetts. At the summit of Mount Greylock you will find the Veterans War Memorial Tower. The 92ft high tower stands as a beacon for peace, to honour those who died during World War I. You can even walk up the inside of the tower for even better views of the surrounding area.
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Adam's Overlook is a great place to stop for a rest on your way up to the summit of Mount Greylock. From here you will be rewarded with beautiful views over Adams. This is a small parking lot with no facilities, but if you keep going up to the summit there is a lodge with facilities. It is worth
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Berkshire County offers a diverse range of touring cycling experiences, from easy, paved rail trails to more challenging on-road routes with significant elevation changes. You'll find paths winding through rolling hills, tranquil valleys, and lush forests, often alongside scenic lakes and rivers like Onota Lake and the Housatonic River.
Yes, Berkshire County is home to several easy and family-friendly options. The Ashuwillticook Rail Trail is a popular choice, offering a gentle, paved surface and scenic views of the Hoosic River Valley, suitable for all skill levels. There are 8 easy routes in total, providing accessible options for beginners and families.
For those seeking a challenge, Berkshire County features routes with significant elevation changes and more demanding terrain. For example, the The Spoke bicycle shop β Fitch Overlook loop from Harriman-and-West Airport is a difficult route with nearly 900 meters of elevation gain. In total, there are 28 difficult routes available for experienced touring cyclists.
Yes, many touring cycling routes in Berkshire County are designed as loops, allowing you to start and end in the same location. A popular example is the Ashuwillticook Rail Trail Head loop from Lanesborough, which offers a moderate 42 km loop experience of the rail trail. Another option is the Ashuwillticook Rail Trail Head loop from North Adams.
Berkshire County's routes often provide stunning vistas. You can enjoy breathtaking views of the Taconic Range and the Catskill Mountains. Specific highlights include the Veterans' War Memorial Tower at the summit of Mount Greylock, Stony Ledge, and Mount Everett Lookout, which offer panoramic views of the surrounding landscape.
Yes, Berkshire County is home to several beautiful waterfalls. While some may require a short hike from the cycling route, notable ones include Bash Bish Falls, the tallest single-drop waterfall in Massachusetts, and the waterfalls at Natural Bridge State Park. Wahconah Falls State Park also offers scenic cascades.
The best time for touring cycling in Berkshire County is generally from spring through fall. The region's lush forests and rolling hills are particularly beautiful in the spring with new growth, and in the fall with vibrant foliage. Summer offers warm weather, but spring and fall provide comfortable temperatures for longer rides.
Absolutely. Many cycling routes pass through or connect charming historic towns like Great Barrington, Lenox, Stockbridge, and Williamstown. These towns offer opportunities to stop at local shops, cafes, and farmer's markets. The region is also known for its cultural institutions, many of which are set amidst beautiful grounds accessible by bike.
The area is highly rated by the komoot community, with an average score of 4.6 stars from over 20 reviews. Reviewers often praise the stunning natural beauty, the variety of terrain from gentle rail trails to challenging climbs, and the peaceful atmosphere of the region's valleys and forests.
Yes, many popular touring cycling routes, especially the rail trails, offer designated parking areas. For instance, the Ashuwillticook Rail Trail has multiple access points with parking available near towns like Lanesborough and Adams, making it convenient to start your ride.
While public transport options directly to trailheads might be limited, some towns in Berkshire County are served by regional bus services. It's advisable to check local transit schedules and routes in advance to see if they align with your chosen starting points for touring cycling.


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