4.7
(29)
1,876
riders
26
rides
If you've ever tried to plan road cycling in Berkshire County, you know how overwhelming the options can be. It's tough to tell which routes are genuinely worth your time and effort, and which are just filler. We get it β you want the highlights, not the guesswork.
That's where we come in. Our komoot community has mapped, ridden, and reviewed countless routes across the Berkshires, so we've done the legwork for you. This guide is a curated shortlist ofβ¦
Last updated: May 11, 2026
5.0
(7)
120
riders
44.0km
01:47
200m
200m
The Ashuwillticook Rail Trail offers a delightful journey through the Hoosac River Valley, providing smooth, paved surfaces perfect for road cycling. You'll glide past the serene Cheshire Reservoir and theβ¦
5.0
(6)
121
riders
If you're looking for a long, easy road cycling route with stunning views, the Cheshire Reservoir β Ashuwillticook Rail Trail Head loop delivers. This 28.8-mile (46.3 km) ride, with aβ¦

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41
riders
61.3km
03:07
1,030m
1,030m
The Ashuwillticook Rail Trail Head β Cheshire Reservoir loop from Adams offers a varied and rewarding road cycling experience. You'll start on the pristine, paved Ashuwillticook Rail Trail, enjoying flat,β¦
33
riders
39.1km
02:19
910m
910m
The Mount Greylock loop from The Clark Art Institute offers a demanding road cycling adventure, leading you through the scenic Mount Greylock State Reservation. You'll navigate winding roads and deepβ¦
33
riders
21.3km
01:23
640m
640m
The Mount Greylock loop from Mount Williams offers a challenging road cycling experience to the highest point in Massachusetts. You'll climb through dense forests, with the scenery gradually opening upβ¦
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Popular around Berkshire County

Traffic-free bike rides in Pittsfield State Forest

Traffic-free bike rides in Balance Rock State Park

Traffic-free bike rides in October Mountain State Forest

Traffic-free bike rides in Mill Brook Reservoir

Traffic-free bike rides around Pittsfield

Traffic-free bike rides in Wahconah Falls State Park

Traffic-free bike rides in Bash Bish Falls State Park

Traffic-free bike rides in Clarksburg State Forest

Traffic-free bike rides in Bates Memorial State Park

Traffic-free bike rides in East Mountain State Forest
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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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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Cheshire Reservoir captivates riders with its tranquil beauty. The scenic reservoir, nestled in the Berkshires, offers stunning views along the route. Cyclists can enjoy a peaceful ride surrounded by nature, appreciating the serenity of Cheshire Reservoir as a highlight of their cycling experience.
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The U.S. Bicycle Route 7 (USBR 7) is a super good, north-south bike trail that follows the Western New England Greenway through Connecticut, Massachusetts, and Vermont. This section in Massachusetts goes past the Cheshire Reservoir and then on past the Hoosic River. It has particularly good views.
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There are over 30 dedicated no traffic road cycling routes in Berkshire County, ranging from easy to difficult. You'll find a diverse selection to suit various skill levels and preferences.
The spring, summer, and especially fall seasons offer ideal conditions for no traffic road cycling in Berkshire County. Fall is particularly stunning with vibrant foliage, though routes can be enjoyed throughout the warmer months. Winter cycling is possible but requires appropriate gear and awareness of conditions.
Yes, Berkshire County offers several easy, no traffic routes perfect for beginners and families. The Ashuwillticook Rail Trail is a prime example, offering a gentle, paved surface through scenic areas, suitable for all skill levels. There are 5 easy routes in total.
For those seeking longer rides, routes like the Ashuwillticook Rail Trail Head β Cheshire Reservoir loop from Adams offer significant distances, extending over 60 kilometers. The region's varied terrain allows for combining sections to create extended, low-traffic cycling experiences.
The komoot community highly rates the no traffic road cycling in Berkshire County, with an average score of 4.7 stars. Cyclists frequently praise the region's stunning natural beauty, the quiet roads winding through charming towns and farmlands, and the variety of terrain, from gentle rail trails to challenging climbs like those found around Mount Greylock.
Yes, you can find several circular no traffic road bike routes. An example is the Cheshire Reservoir β Ashuwillticook Rail Trail Head loop from Western District HQ, which provides a scenic loop experience. Many routes are designed to bring you back to your starting point, offering convenient cycling options.
Many popular no traffic routes, especially rail trails like the Ashuwillticook, have designated parking areas at their trailheads. For example, the Ashuwillticook Rail Trail Head offers convenient access and parking. Specific parking information is often available on individual route pages.
E-bike regulations can vary by specific trail or road. Generally, Class 1 and Class 2 e-bikes are permitted on paved rail trails and roads where traditional bicycles are allowed. Always check local signage or specific route guidelines for any restrictions before you ride.
Berkshire County's no traffic routes offer numerous scenic viewpoints. You can enjoy panoramic vistas from places like Olivia's Overlook. Routes around Mount Greylock, such as the Mount Greylock loop from The Clark Art Institute, also provide breathtaking views, especially from the summit.
While specific routes may not pass directly by all, Berkshire County is rich in natural features. Notable waterfalls in the region include Natural Bridge State Park, Tannery Falls, Wahconah Falls, and Race Brook Falls. Many routes wind through forests and past lakes like Cheshire Reservoir and Benedict Pond, offering beautiful natural scenery.
The region is dotted with cultural and historical landmarks. While cycling, you might pass by historic estates, charming small villages, and cultural institutions. The Veterans' War Memorial Tower at the summit of Mount Greylock is a significant landmark accessible on some routes. The overall landscape combines natural beauty with a rich cultural heritage.
Many no traffic routes, especially those passing through or near towns like Cheshire, Lanesborough, and Adams along the Ashuwillticook Rail Trail, offer access to cafes, restaurants, and other amenities. Planning your route can help you identify convenient stops for refreshments or supplies.


Check out more Road cycling routes throughout Berkshire County below and find the perfect route in your destination.
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