Explore the best rated trails in Greenfield, MA, whether you're looking for an easy walking trail or a bike trail like the Common Pathway and Appel Way Trail . With more than 50 trails covering 399 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
We walked along the towpath section in Uxbridge and it was lovely. My daughter is in a wheelchair and it was doable, if not perfect. Park and enter from the Visitors' Center, and watch for the rocks and roots.
I love this trail! Rode it on 3/14/24 when weather was 62 degrees. This trail is short but can be expanded if you cross the metal bridge by the brewery and take the road to the left leading to the Fish Research Hatchery on the opposite side of the canal. If you meander through the little neighborhood on that side as well you can extend it further and get another view of the old mill complexes. I get 20 miles out of the ride. Bring a lunch there are picnic tables on both sides!
It looked very nice from the parking area, but could not get through the barricades with a recumbent trike. Drove over an hour and gates were shut and would have had to lift trike over gates. Disgusted with Massachusetts and whomever designed the barricades. Has anyone heard of the ADA?
Excellent experience on this fresh paved trail. The scenery of the ponds and mountains in the distance was worth the trip.
A sidepath has been constructed adjacent to Route 189 to Main St in Tariffville. Trail is now about 3 miles long. It will be designated as part of the East Coast Greenway and is visible on Google Street View.
Cheshire Trail South. Rode north from State Line Circle toward Kenne. We are experienced road cyclists, now riding gravel bikes. We are looking for reasonably surfaced longer trails and hoped this would be one of them. Sadly, we found this trail to be rocky, rutted, with lots of roots, and uncleared blowdown. The vigilance required to remain upright made it difficult to enjoy the beauty all around. The suddenly occurring steep inclines to roads seemed borderline dangerous. If we lived closer it would be a great trail to walk with the dogs
I would hate for people to avoid this lovely trail because of reports of the washouts. By using the trail map from this app or even Google maps you can easily find nearby roads that allow you to ride around the closed sections. We had a lovely 18.7 mi ride today and we’re able to keep cool because of lots of shade even though it got up to 90 degrees! They were repairing the bridge on the road to the Slate Covered Bridge, but they paused work to let us cross. It will be repaired very soon.
Truly a nice ride this weekend. Packed surface, mixed terrain but nothing our Surly Ogre's couldn't handle. This was not a crowded trail but there were a spattering of walkers, bikers, dog walkers. Made you feel happy to be alive! Whoever is maintaining this trail - thank you!
What will it take to get the Bennington to Deering Rail Trail suitable for bicycle??? It is a very difficult ride with even fat-tired riders because of the loose terrain. And then if you try to avoid it by riding the road, that is almost impossible also due to all the pitfalls and holes. This could be such an attraction.
I tried the Jaffrey to Rindge trail this weekend and there was NO COMPARISON! Fun, enjoyable ride while this one remains disappointing.
Please put this one on your list to help!!!
I rode the trail from Pittsfield to the end in North Adams and back on 8/5/23. The trail is paved and in good condition and restrooms at the Pittsfield trail head were clean and working fine. Nice scenery including lakes and the Berkshires- I was able to finally identify Mt Greylock after the morning clouds had dissipated. The grade is gentle and I was able to keep up a consistent pace for the ride.
A mix of sand, packed gravel and flooded trail. Rather challenging terrain that required skilled navigating the trail . It was in horrible condition. The brewery in winchendon was wonderful, but you need to bushwhack through the trail and into an abandoned factory’s parking lot.
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