4.7
(4)
53
hikers
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hikes
Hiking around Greenfield, Massachusetts, offers access to a landscape characterized by forested hills, river valleys, and varied elevation changes. The region features state reservations and conservation areas, providing a mix of trails. Hikers can explore paths leading to scenic viewpoints and through diverse natural features. The terrain includes river valleys, forested hills, and mountain viewpoints.
Last updated: April 26, 2026
7
hikers
3.25km
00:56
80m
70m
Embark on an easy 2.0-mile (3.3 km) hike along the Dutch and Mary Barnard and Waterthrush Trail Loop, a route that takes about 55 minutes to complete. You will experience…
1
hikers
3.87km
01:05
70m
90m
Hike the Rocky Mountain Poets Seat Trail for an easy 2.4-mile (3.9 km) journey that takes about 1 hour and 5 minutes. You will gain 232 feet (71 metres) in…

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1
hikers
2.33km
00:43
90m
60m
Embark on an easy hike along the Upper Greenfield Reservoir via Leyden Glen, a peaceful out-and-back route that guides you through classic wooded areas. You'll enjoy serene views of the…
1
hikers
4.86km
01:30
190m
150m
Embark on an easy hiking adventure along the Satan's Kingdom Trail, a 3.0-mile (4.9 km) route that winds through dense forests and open meadows. Despite its easy rating, you will…
2.23km
00:36
10m
60m
Embark on an easy hike along a segment of the Mahican-Mohawk Trail, a route that offers a peaceful escape into nature. This trail covers a distance of 1.4 miles (2.2…
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The summit ridge has lots of exposed stone that lends itself to fun, quintessential New England hiking. The trail takes you to High Ledge and you get views stretching out in multiple directions as you peek out of the trees.
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Hiking around Greenfield, Massachusetts, features a landscape of forested hills and river valleys. You'll find trails with varied elevation changes, from easy, relatively flat paths to moderate climbs through wooded areas.
Yes, Greenfield offers several easy trails. For example, the View of Deerfield River Valley – Dutch and Mary Barnard Trail loop from Shelburne is an easy 3.5-mile (5.6 km) path with scenic views. Another easy option is the Massamet Mountain Fire Tower loop from Buckland, which is 2.7 miles (4.4 km) through forests.
Absolutely. The View of Deerfield River Valley – Dutch and Mary Barnard Trail loop from Shelburne provides excellent views of the Deerfield River Valley. Additionally, the Massamet Mountain Fire Tower loop from Buckland leads to a fire tower, which typically offers expansive vistas of the surrounding area.
Beyond the scenic river valleys and forested hills, you can explore highlights like the Dutch and Mary Barnard Trail itself, which is a significant natural feature. The area also features the Connecticut River Greenway State Park, offering riverine landscapes.
Yes, many of the trails around Greenfield are designed as loops. Examples include the Mount Toby loop from Montague, the View of Deerfield River Valley – Dutch and Mary Barnard Trail loop from Shelburne, and the Massamet Mountain Fire Tower loop from Buckland, all of which are circular routes.
The hiking routes in Greenfield are highly rated by the komoot community, with an average score of 5.0 stars. Hikers often praise the varied terrain, scenic viewpoints, and the well-maintained paths through conservation areas.
The easy-rated trails are generally suitable for families. The View of Deerfield River Valley – Dutch and Mary Barnard Trail loop from Shelburne, at 3.5 miles, offers an accessible and scenic option for a family outing. The Massamet Mountain Fire Tower loop from Buckland is also an easy, shorter option at 2.7 miles.
While specific parking details for every trailhead are not listed here, trails in state reservations and conservation areas typically have designated parking lots. It's always advisable to check route details on komoot for specific parking information before you go.
Greenfield offers enjoyable hiking throughout much of the year. Spring brings lush greenery, summer provides warm weather for exploring, and autumn is particularly popular for its vibrant fall foliage. Winter hiking is also possible, though conditions may require appropriate gear.
For a moderate challenge, consider the Mount Toby loop from Montague. This 5.4-mile (8.7 km) route features forest paths and notable elevation gain, taking approximately 2 hours and 34 minutes to complete.
While specific 'hidden gems' are subjective, exploring trails within the various state reservations and conservation areas beyond the most popular routes can often lead to quieter experiences. The region has a network of paths that offer solitude amidst nature.


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