5.0
(14)
421
riders
8
rides
Road cycling around Pittsfield, Massachusetts, is characterized by its varied terrain within the Berkshire Hills, offering a mix of dedicated paved trails and quiet rural roads. The region features significant natural landmarks such as Lakes Onota and Pontoosuc, the Housatonic River, and expansive areas like Pittsfield State Forest. Cyclists can navigate routes that traverse gentle valleys, pass by scenic reservoirs, and include moderate climbs through forested landscapes.
Last updated: May 12, 2026
5.0
(7)
116
riders
44.0km
01:47
200m
200m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(6)
121
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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7
riders
44.8km
01:58
420m
420m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
47.9km
02:12
490m
490m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
3
riders
38.0km
01:40
360m
360m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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This is the most beautiful rail trail in Massachusetts hands down.
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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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The Joseph Scelsi ITC exemplifies the journey of many train stations across the US. From grand historical structures to modern intermodal centers, they reflect the evolution of transportation needs and preferences. The seasonal "Berkshire Flyer" offers a glimpse into the past, reminding us of the charm and romance associated with train travel.
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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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Head down Lakeway Drive to find Onota Lake. Onota Lake offers a host of water-based recreational opportunities in all seasons. With its unparalleled scenic beauty, this high-quality lake naturally attracts boaters, fisherman, and nature enthusiasts from around the region.
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There are over 8 dedicated no-traffic road cycling routes around Pittsfield, offering a variety of experiences for different skill levels. You'll find a mix of easy and moderate rides to explore.
The no-traffic road cycling routes around Pittsfield cater to a range of abilities. You'll find 2 easy routes, perfect for a relaxed ride, and 6 moderate routes for those looking for a bit more challenge.
The Ashuwillticook Rail Trail is a premier attraction for no-traffic road cycling in the region. It's a paved, 10-foot-wide path stretching over 44 km through Pittsfield, Lanesborough, Cheshire, and Adams. It offers scenic views of wildlife, the Cheshire Reservoir, and the Hoosic River, making it suitable for various fitness levels with minimal elevation gain.
Yes, several routes offer a circular experience. For example, the Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Western District HQ provides a scenic 46 km ride. Another option is the Gould Meadows loop from Pittsfield, which is a longer, moderate 57 km route.
Many routes offer beautiful natural scenery and points of interest. Along the Ashuwillticook Rail Trail, you'll pass by the Cheshire Reservoir and the Hoosic River. Other routes might take you near Lakes Onota and Pontoosuc, or offer vistas like Olivia's Overlook. The region is rich in natural beauty, including parts of the Housatonic River and the Berkshire Hills.
Absolutely. The Ashuwillticook Rail Trail, with its paved, flat surface and scenic views, is particularly well-suited for families. Its gentle terrain and lack of vehicle traffic make it a safe and enjoyable option for cyclists of all ages.
The spring, summer, and fall months generally offer the best conditions. The Berkshire Hills are especially renowned for breathtaking fall foliage, making autumn a spectacular time to cycle. June is also notable for the wild azalea fields blooming profusely in Pittsfield State Forest, which can be accessed via nearby routes.
For the popular Ashuwillticook Rail Trail, there are various parking options available along its length in Pittsfield, Lanesborough, Cheshire, and Adams. Specific parking areas are usually well-marked at trailheads. For other routes, parking may be available at designated trail access points or public parking areas in Pittsfield.
The area is highly rated by the komoot community, with an average score of 5.0 stars from 14 ratings. Reviewers often praise the serene, car-free environment, the well-maintained paved trails like the Ashuwillticook Rail Trail, and the beautiful natural scenery of the Berkshire Hills.
While the Ashuwillticook Rail Trail is a highlight, other routes offer similar no-traffic experiences or utilize quiet roads. For instance, the Cheshire Reservoir – Trail start loop from Pittsfield offers a moderate ride with significant elevation gain, providing a different challenge while still focusing on low-traffic areas. The broader Berkshire region also features quiet roads that connect to various towns and natural features.
Yes, some routes might bring you close to historical points of interest. For example, the Hancock Shaker Village is a notable historical site in the region, offering a glimpse into Shaker life and architecture. While not directly on a no-traffic path, it's an attraction worth considering in conjunction with your ride.


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