4.6
(8)
179
riders
32
rides
Touring cycling around Pittsfield, Massachusetts, offers diverse routes through the scenic Berkshire Mountains. The region features varied landscapes, including dedicated rail trails, expansive state forests, and numerous lakes. Cyclists can explore terrain ranging from flat, paved paths to challenging ascents, with elevations reaching over 3,400 feet at Mount Greylock. The area is characterized by its mix of woodlands, open fields, and waterways like the Housatonic River.
Last updated: May 1, 2026
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.
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.
8
riders
46.7km
03:15
870m
870m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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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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Tower can be climbed
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Visible from afar, the Veterans War Memorial Tower at the top of Mount Greylock was erected in 1934 in memory of all who served the U.S. during World War I. The tower measures 93 feet and was selected as one of the 100 Official World War I Centennial Memorials in 2018 to commemorate the 100th anniversary of the end of the war. Mount Greylock itself towers 3,489 feet above Massachusetts and is also the highest elevation in the state. The iconic Appalachian Trail leads up to it.
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Pittsfield offers a wide variety of touring cycling experiences, with over 30 routes available. These routes cater to different skill levels, from easy, paved trails to challenging ascents through the Berkshire Mountains.
The routes around Pittsfield offer a diverse range of difficulties. You'll find 3 easy routes, 15 moderate routes, and 14 difficult routes, ensuring options for cyclists of all experience levels. The region is known for its varied terrain, from flat rail trails to demanding mountain climbs.
The touring cycling routes in Pittsfield are highly rated by the komoot community, with an average score of 4.6 stars from more than 8 reviews. Cyclists often praise the scenic views, diverse landscapes, and the quality of the trails, particularly the Ashuwillticook Rail Trail.
Yes, the Ashuwillticook Rail Trail is a highlight for touring cyclists. This paved, 10-foot-wide trail spans through Pittsfield and surrounding towns, offering scenic views of wildlife, the Cheshire Reservoir, and the Hoosic River. It's a mostly flat and accessible option, perfect for a relaxed ride. One popular route on this trail is the Ashuwillticook Rail Trail Head loop from Lanesborough.
Pittsfield's cycling routes showcase the region's stunning natural beauty. You can expect to see the expansive Pittsfield State Forest with its diverse terrain, streams, and wild azalea fields in June. Lakes like Pontoosuc Lake and Onota Lake offer beautiful views. The Housatonic River flows through the area, with conservation areas like Canoe Meadows Wildlife Sanctuary providing opportunities for wildlife spotting. For panoramic vistas, consider routes that pass by Olivia's Overlook or ascend Mount Greylock.
Absolutely. For experienced cyclists seeking a challenge, routes like the Ashuwillticook Rail Trail Head – Fitch Overlook loop from Lanesborough offer significant elevation gain, providing panoramic views of the surrounding Berkshire landscape. Mount Greylock, the highest point in Massachusetts, also presents a demanding ascent for serious riders, with breathtaking rewards at the summit.
Several routes offer stunning panoramic views. The Ashuwillticook Rail Trail Head – Fitch Overlook loop from Lanesborough provides expansive vistas. In Pittsfield State Forest, the vista from Berry Mountain offers striking panoramic views, ideal for sunsets. Additionally, Olivia's Overlook is a notable viewpoint in the area.
Yes, Pittsfield offers several family-friendly options. The Ashuwillticook Rail Trail is particularly suitable, being a paved, mostly flat path that is accessible for all skill levels. Pittsfield State Forest also features the paved 0.75-mile Tranquility Trail, which is wheelchair-accessible and great for short, easy rides.
Many outdoor areas in Pittsfield are dog-friendly. For example, Burbank Park on Onota Lake features a dedicated dog-friendly area and wide-open fields suitable for walks with your pet. The Ashuwillticook Rail Trail generally allows leashed dogs, making it a great option for cycling with your canine companion. Always check specific trail regulations before you go.
Yes, many of the touring cycling routes around Pittsfield are designed as loops, allowing you to start and end at the same point. A popular example is the Bike loop from Pontoosuc, which takes you through areas near Pontoosuc Lake. The Ashuwillticook Rail Trail Head loop from Lanesborough is another excellent circular option.
Free parking is readily available for many popular cycling routes. For the Ashuwillticook Rail Trail, you can find parking at the Crane Avenue entrance in Pittsfield. Other parks and trailheads throughout the region, such as Burbank Park, also offer designated parking areas for visitors.
The best season for touring cycling in Pittsfield is generally spring through fall, when the weather is mild and the natural landscapes are vibrant. June is particularly beautiful with the wild azalea fields blooming in Pittsfield State Forest. The fall foliage in the Berkshire Mountains also makes for spectacular rides. While the Ashuwillticook Rail Trail is open year-round, winter cycling may require appropriate gear for colder conditions.
Pittsfield is home to several beautiful lakes and parks that are easily accessible from cycling routes. Pontoosuc Lake Park offers a sandy beach and picnic areas. Burbank Park on Onota Lake provides over 150 acres with a fishing pier and boat launch. Springside Park, Pittsfield's largest green space, features wooded trails and open fields. Many routes, like the Bike loop from Pontoosuc, will take you directly past these scenic spots.


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