5.0
(3)
108
riders
6
rides
Gravel biking around Greenfield, Massachusetts, offers a landscape characterized by challenging terrain, significant elevation changes, and classic New England scenery. The region features a mix of paved and unpaved surfaces, including forested valleys and dirt roads, with minimal traffic. The Green River Valley and historic covered bridges are prominent natural features along many routes.
Last updated: May 12, 2026
5.0
(2)
36
riders
92.0km
06:12
1,640m
1,640m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
10
riders
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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10
riders
99.9km
07:50
2,020m
2,020m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
7
riders
92.9km
06:06
1,510m
1,510m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Greenfield
There is a small green space near bridge that is a great place to stop for a snack or lunch.
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Settlers first established Heath in 1765 and named it after General Heath, who served as a commanding officer in the national army during the American Revolution. This location serves as a common area, housing the town hall and featuring a pleasant green space with benches for taking breaks.
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As you ride along the crystal-clear waters of the Green River, surrounded by the picturesque landscape of this stunning region, take a moment to immerse yourself in the natural beauty surrounding you. In the fall, the foliage of the trees adds to the already spectacular scenery of this wondrous place.
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Historic covered bridges such as this one are traditional in the area, and it is great to see them maintained. The Bissel Covered Bridge was built in 1881. By the mid-20th century the bridge was due to be replaced by a modern steel and concrete structure. The local town opposed the new structure, and the original bridge was rebuilt and kept to the original specifications. The bridge still features a wooden structure and wooden floor.
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Stillwater Bridge on Upper Road gives you fantastic views over the Deerfield River. This is a beautiful spot to pause and take in the views over the water as you ride around the area.
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The Eunice Williams Covered Bridge, or the Pumping House Station Bridge, crosses the Green River and is one of only 12 covered bridges left in Massachusetts. This is a great place to ride by and soak in a bit of unique regional architectural history!
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Also called Pumping House Station Bridge. One of just a handful of covered bridges in Massachusetts
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Really pretty stretch of dirt road in Colrain. The road was in really good shape as of Oct 2022. I had no problems on it at all on a hybrid bike
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There are 7 curated no-traffic gravel bike routes around Greenfield, Massachusetts, designed for a range of abilities. These routes focus on providing a serene experience away from vehicular traffic, allowing you to immerse yourself in the picturesque New England scenery.
While many routes in Greenfield, MA, feature significant elevation and are rated as difficult, there is one moderate route suitable for those looking for a less strenuous ride. The Green River Road, Colrain – Green River Covered Bridge loop from Green River Wildlife Management Area is a 37 km loop with 342 meters of elevation gain, offering a good option for intermediate riders or families with some gravel biking experience. For beginners, the area's challenging terrain might require a bit more preparation.
You can expect classic New England gravel roads, forested valleys, and a mix of paved and unpaved surfaces. Some routes feature significant elevation changes, with challenging climbs and descents. Trails like those around the Green River Valley offer varied terrain, from smoother gravel to rougher, rocky sections, ensuring a true gravel biking adventure.
Many routes will take you through the beautiful Green River Valley, offering sweeping views and opportunities to see historic covered bridges. The Green River Covered Bridge – Green River Road, Colrain loop from Greenfield is a prime example, passing by the iconic Eunice Williams Covered Bridge. Other nearby attractions include the Canalside Rail Trail and the Turner's Falls Bridge, which offer additional scenic points of interest.
Yes, all the no-traffic gravel bike routes featured in this guide are circular loops, allowing you to start and end your ride at the same point. This makes planning your trip, especially regarding parking, much more convenient. For instance, the Stillwater Bridge – Bissell Bridge loop from Greenfield is a challenging 99 km circular route.
The best time for gravel biking in Greenfield, MA, is typically during the spring, summer, and fall months. Spring brings wildflowers and lush greenery, while fall offers spectacular foliage. The region's varied terrain can be challenging after heavy rains, so checking local conditions is always recommended, especially for rougher sections like Cobble Hill Road.
The no-traffic gravel routes around Greenfield are highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the immersive experience of riding through quiet woodlands, the challenging yet rewarding elevation changes, and the stunning New England scenery, particularly the covered bridges and Green River Valley views.
Absolutely. Greenfield, MA, is known for its challenging gravel terrain. Routes like the Eunice Williams Covered Bridge – Green River Road, Colrain loop from Greenfield, spanning over 92 km with more than 1500 meters of elevation gain, are rated as difficult and require very good fitness. These routes offer significant climbs and descents, perfect for experienced gravel bikers seeking a demanding adventure.
Many of the circular routes start from Greenfield itself, making it convenient to find parking within the town. For routes that begin outside the main town, such as those from the Green River Wildlife Management Area, designated parking areas are usually available. It's always a good idea to check the specific tour details on komoot for recommended starting points and parking information.
Yes, the Green River Valley, which many of these no-traffic gravel routes traverse, is known for its picturesque views, including occasional waterfalls. While not explicitly highlighted on every route, the natural landscape of the valley provides opportunities to encounter these beautiful features, especially after periods of rain.
While Greenfield, MA, has some local public transport options, direct access to the more remote gravel trailheads can be limited. It's generally recommended to plan your trip with a vehicle to reach the starting points of these no-traffic routes, especially for those venturing deeper into the Green River Valley or other rural areas.


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