5.0
(2)
10
riders
4
rides
Gravel biking around Pittsfield offers diverse terrain within the scenic Berkshire Mountains, characterized by extensive woodlands and varied landscapes. The region features a network of forest roads and paths with significant elevation changes, providing a range of gravel biking experiences. Pittsfield State Forest, an 11,000-acre woodland, is a central hub for these activities, offering routes through dense forests and past serene ponds. The area's natural features include numerous hills and streams, creating a dynamic environment for gravel cyclists.
Last updated: May 15, 2026
5.0
(2)
4
riders
41.5km
03:00
660m
660m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
26.4km
02:02
470m
470m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Sign up for free
2
riders
39.3km
03:24
560m
560m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
34.2km
02:27
560m
560m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
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.
0
0
Gould Meadows, a little off of Road 183, is a conservation property, owned by the Town of Stockbridge. It has a total of 95 acres of conservation land with 0.6 miles of public trails. It is open to the public.
0
0
Hawthorne Road runs along the shore of Stockbridge Bowl. It's original name is Lake Mahkeenac. Mahkeenac means 'home of the Mahekanus' and it was given this name by the Mahican Indians, a tribe of the Mohicans.
0
0
Gould Meadows, a little off of Road 183, is a conservation property, owned by the Town of Stockbridge. It has a total of 95 acres of conservation land with 0.6 miles of public trails. It is open to the public.
0
0
Gravel biking around Pittsfield offers diverse terrain, primarily within the scenic Berkshire Mountains. You'll encounter extensive networks of forest roads and paths with varied surfaces, including gravel, dirt, and some rocky sections. Many routes feature significant elevation changes, providing both challenging climbs and rewarding descents. For example, the Cone Hill loop is known for its sustained climbs and varied forest surfaces.
While many routes in the Pittsfield State Forest are considered difficult due to elevation, there are options for varying skill levels. The region offers a mix of paths, and some areas like the Barkerville Conservation Area provide mostly flat gravel trails, though they can have rocky sections. For a more relaxed experience, the paved Ashuwillticook Rail Trail is excellent for all ages and skill levels, offering stunning Berkshire vistas.
The Pittsfield area is rich with natural beauty and points of interest. Within Pittsfield State Forest, you can find serene spots like Berry Pond and Lulu Pond. For expansive views, consider routes that offer glimpses of the broader Berkshire landscape. While not directly on a gravel route, Olivia's Overlook provides a fantastic vista. The Hancock Shaker Village also features a scenic trail that can be explored by cyclists.
For families, the paved Ashuwillticook Rail Trail is an excellent choice, offering a safe and scenic 13.7-mile path. While many gravel routes in Pittsfield State Forest are more challenging, some sections of the Barkerville Conservation Area offer flatter, less technical gravel trails suitable for families with some biking experience. Always check route details for specific difficulty and terrain before heading out with children.
Many outdoor areas in the Berkshires, including parts of Pittsfield State Forest, are dog-friendly. However, leash laws and specific regulations can vary by trail and conservation area. It's always best to check local signage or the specific park's website before bringing your dog. Ensure your dog is well-behaved and can handle the varied terrain and potential wildlife encounters.
The shoulder seasons of spring (late April to June) and fall (September to October) are often considered ideal for gravel biking in Pittsfield. During these times, temperatures are pleasant, and the natural scenery is at its peak, with lush greenery in spring and vibrant foliage in autumn. Summer can be enjoyable, but be prepared for warmer temperatures and potential humidity. Winter riding is possible for experienced cyclists, but trails may be covered in snow or ice.
Many popular gravel biking areas, such as Pittsfield State Forest, offer designated parking lots at trailheads. For example, routes like the Shermerhorn Hill loop and Cone Hill loop often start from areas with accessible parking. It's advisable to check the specific route details on komoot or local park websites for precise parking information before your ride.
Yes, many of the gravel biking opportunities around Pittsfield are designed as loops, allowing you to start and end at the same point. Popular examples include the Shermerhorn Hill loop and the Gould Meadows – Gould Meadows loop. These circular routes provide a comprehensive experience of the region's diverse terrain and woodlands.
The komoot community highly rates the gravel biking experience in Pittsfield, with an average score of 5.0 stars. Reviewers often praise the extensive woodlands, varied terrain, and the sense of immersion in nature. Cyclists appreciate the challenging climbs and rewarding descents found on routes like the Shermerhorn Hill loop, as well as the overall beauty of the Berkshire Mountains.
Yes, the Pittsfield region is home to several beautiful lakes and ponds. While specific gravel routes may not always hug the shoreline, you can find options that offer views or pass near water bodies. For instance, the Cheshire Reservoir loop provides scenic views of Cheshire Reservoir. Pittsfield State Forest also features Berry Pond and Lulu Pond, offering tranquil spots amidst your ride.
Komoot features a selection of 5 curated gravel bike routes around Pittsfield, ranging from moderate to difficult. These routes provide a good starting point for exploring the region's diverse gravel biking opportunities. Beyond these, the extensive network of forest roads and unmaintained paths in areas like Pittsfield State Forest offers countless possibilities for exploration.
While many routes are designed as day trips, the extensive network of trails and unmaintained roads in the Berkshires allows for longer, self-planned adventures. Routes like the Shermerhorn Hill loop (36.3 miles) and the Cone Hill loop (25.8 miles) offer substantial distances. By linking various trails and gravel roads, experienced riders can create multi-day tours through the scenic Berkshire Mountains.


Browse the best Gravel rides in other regions.