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Road cycling in Middlefield State Forest, located in the Berkshire Plateau of Western Massachusetts, offers varied terrain across rolling hills and dense woodlands. The region is characterized by lush greenery, diverse tree species like white pine, oak, and maple, and serene natural features. Road cycling routes here navigate through these landscapes, providing a mix of challenges and scenic views. The area's geology, shaped by receding glaciers, contributes to its varied topography.
Last updated: May 17, 2026
3
riders
61.3km
03:09
900m
900m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
1
riders
44.6km
02:13
690m
690m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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1
riders
57.8km
03:03
830m
830m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
1
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Popular around Middlefield State Forest
This is the site of the ruins of the Plunkett Brothers Mill. The mill was working until 1930 and produced a range of textiles, including blankets, shirts and skirts. The mill was run on energy created by the Housatonic River. Once the mill shut down, it was abandoned and over the 90 years, nature has slowly reclaimed the area.
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This small natural area is primarily a residential neighborhood, characterized by lush greenery and a pleasing elevation change. It presents an enjoyable and challenging ride to reach this location.
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Middlefield State Forest offers a tranquil escape with its dense woodlands, scenic trails, and recreational opportunities like hiking, cycling, picnicking, and birdwatching.
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This reserve is a hidden gem along the East Branch of the breathtaking Housatonic River. The area is a treasure trove of fascinating historical sites, including a centuries-old dam, the Plunkett Brothers mill, and the remains of an awe-inspiring penstock that once channeled water to the mills of Dalton. This land's rugged and spectacular natural beauty is an absolute feast for the eyes, with towering boulders and lush hemlock groves that beckon you to explore.
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Cycling along East River Road in Fox Den Wildlife Management Area offers encounters with diverse wildlife and lush foliage. The road meanders through woodlands where cyclists may spot white pine, oak, and maple trees. Wildlife sightings can include deer, songbirds, and various woodland creatures, enriching the cycling experience.
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Lake Ashmere is used mostly for private recreational purposes and has a number of summer camps dotted along its shore. It is not open to the general public, but the view over the bridge makes for a stunning view when you pass by on your bike.
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Dalton is a pretty little town of about 6,500 people that was first settled in 1755. Since 1873, the Crane & Co. located there has been the sole supplier of the United States' paper money and the town's largest employer. In addition, Dalton is a stop along the Appalachian Trail. Here you'll find restaurants, grocery stores and lodging.
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Middlefield State Forest offers a selection of road cycling routes, with four distinct tours currently available on komoot. These routes cater to various fitness levels, ranging from moderate to difficult.
You can expect varied terrain characterized by rolling hills and dense woodlands. The routes wind through lush greenery with diverse tree species like white pine, oak, and maple. The landscape, shaped by receding glaciers, contributes to its varied topography, offering both scenic beauty and engaging challenges.
The road cycling routes in Middlefield State Forest range from moderate to difficult. Moderate routes typically require good fitness, while difficult routes demand very good fitness due to significant elevation gains. For example, the Cherry Tree Hill – View of Lake Ashmere Bridge loop from Peru is classified as difficult, featuring over 900 meters of elevation gain.
Yes, experienced riders looking for a challenge can tackle the Cherry Tree Hill – View of Lake Ashmere Bridge loop from Peru. This difficult route spans 61.3 km and includes over 900 meters of elevation gain, making it a demanding ride through the forest's varied terrain.
Absolutely. Several moderate routes are available, perfect for those with good fitness. The View of Lake Ashmere Bridge – Dalton loop from Hinsdale is a popular choice, covering 44.6 km with approximately 690 meters of elevation gain. Another option is the View of Lake Ashmere Bridge – Middlefield State Forest loop from Hinsdale, which is 57.2 km long with about 831 meters of ascent.
For a shorter ride, consider the Peru Wildlife Management Area – Cole Street Conservation Area loop from Westfield River Access. This moderate route is approximately 22.6 km long with around 380 meters of elevation gain, offering a quicker yet engaging experience.
Yes, several routes provide scenic views of water features. The View of Lake Ashmere Bridge – Dalton loop from Hinsdale and the View of Lake Ashmere Bridge – Middlefield State Forest loop from Hinsdale both offer glimpses of Lake Ashmere and its surrounding natural beauty. Additionally, Tracy Pond borders the State Forest, providing a tranquil natural setting.
Middlefield State Forest and its adjacent areas are home to diverse wildlife. Cyclists might spot white-tailed deer and various woodland creatures. The nearby Tracy Pond Wildlife Management Area is known for its abundance of wildlife, including black bears, offering a chance for nature observation during your ride.
The region's lush greenery and diverse tree species suggest that spring, summer, and fall would be ideal. Spring brings fresh foliage, summer offers warm weather, and autumn provides stunning fall colors. The tranquil nature of the forest makes it a pleasant destination for outdoor activities during these seasons.
While many segments of the road cycling routes in Middlefield State Forest feature mostly well-paved surfaces, some routes may include unpaved or more challenging sections. This mix offers varied experiences for cyclists, from smooth stretches to more rugged terrain.
Road cyclists appreciate the varied terrain across rolling hills and dense woodlands, providing a mix of challenges and scenic views. The tranquil natural retreat, characterized by lush greenery and diverse tree species, is often highlighted as a key draw. The area's established routes cater to different ability levels, making it accessible for many.


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