5.0
(3)
114
riders
16
rides
Gravel biking around Greenfield offers a diverse landscape characterized by river valleys, rolling hills, and rural roads. The region features significant elevation changes, providing varied terrain for gravel cyclists. This area, known for its scenic covered bridges and proximity to the Green River, presents a mix of challenging climbs and picturesque routes.
Last updated: April 27, 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.
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.

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4
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
50.3km
03:23
650m
650m
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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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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Mill River is part of the Cushman Brook and flows through to the Cushman Brook Conservation Area and the Mill River Conservation Area. This river is in a thickly forested area in a ravine. Some of this protected area was donated and some was purchased. Visiting Mill River is a family-friendly get-away into nature open for the public to enjoy.
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On this side of Depot Road, you can enjoy a good view of Leverett Pond from its boat launch point. The bottom of this pond is completely covered by submerged vegetation.
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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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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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Mill River is part of the Cushman Brook and flows through to the Cushman Brook Conservation Area and the Mill River Conservation Area. This river is in a thickly forested area in a ravine. Some of this protected area was donated and some was purchased. Visiting Mill River is a family-friendly get-away into nature open for the public to enjoy.
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There are over 20 gravel bike trails documented around Greenfield on komoot, offering a wide range of options for different skill levels and preferences.
Gravel biking around Greenfield features a diverse landscape of river valleys, rolling hills, and rural roads. You'll encounter significant elevation changes, providing varied terrain from challenging climbs to picturesque routes through forested sections and open areas. The region is known for its scenic covered bridges and proximity to the Green River.
While many routes in Greenfield involve significant elevation, there are several moderate options that could be suitable for beginners looking for a challenge. For example, the Green River Road, Colrain – Green River Covered Bridge loop from Green River Wildlife Management Area is a moderate 23.1-mile (37.2 km) route with less elevation gain compared to the more difficult trails.
Many routes will take you past scenic spots like the Green River Covered Bridge. You can also explore nearby attractions such as the Canalside Rail Trail - Canal Section, the historic Turner's Falls Bridge, or the Connecticut River Greenway State Park, which offers additional trails and natural beauty.
Yes, many of the gravel bike routes around Greenfield are designed as loops. A popular option is the Eunice Williams Covered Bridge – Green River Road, Colrain loop from Connecticut River Greenway State Park, a challenging 49.0-mile (78.9 km) path that explores riverine areas and offers varied terrain.
The komoot community highly rates the gravel biking experience in Greenfield, with an average score of 5.0 stars. Riders often praise the diverse terrain, from challenging climbs to scenic river valleys, and the opportunity to explore rural roads and covered bridges. Over 120 gravel bikers have used komoot to discover the varied landscapes here.
Absolutely. For experienced riders seeking a challenge, the Green River Covered Bridge – Green River Road, Colrain loop from Greenfield is a difficult 57.2-mile (92.0 km) trail with substantial elevation gain, typically taking over 6 hours to complete. Another demanding option is the Green River Road, Colrain – Colwell Hill loop from Green River Wildlife Management Area, a 36.5-mile (58.7 km) route through hilly and forested sections.
Given the region's varied topography and potential for snow or ice in winter, spring, summer, and fall generally offer the best conditions for gravel biking. Fall is particularly scenic with foliage, while spring and summer provide lush green landscapes. Always check local weather conditions before heading out.
Many of the routes around Greenfield traverse rural roads and forested sections, offering a sense of tranquility away from busier areas. The trails leading through river valleys and less populated areas, such as parts of the Green River Road, Colrain – Green River Covered Bridge loop from Greenfield, often provide a peaceful riding experience.
While specific public transport options directly to every trailhead may vary, Greenfield itself has local bus services. For accessing routes, especially those starting from locations like the Connecticut River Greenway State Park, it's advisable to check local transit schedules or consider driving to a suitable starting point with parking.
For families or those looking for less strenuous rides, consider exploring sections of the Canalside Rail Trail. While not exclusively gravel, rail trails often provide flatter, well-maintained surfaces suitable for a family outing. For dedicated gravel, look for the moderate-difficulty routes that are shorter in distance.


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