Looking for the best trails around Greenfield?

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 398 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.

Recent Trail Reviews

Ashuwillticook Rail Trail

Not ADA compliant

February, 2024 by ljt trike rider

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?

Ashuwillticook Rail Trail

Great fall ride.

November, 2023 by cantabty

Excellent experience on this fresh paved trail. The scenery of the ponds and mountains in the distance was worth the trip.

Bloomfield Greenway Multi-Use Trail

Extension to Tariffville is complete

November, 2023 by bcgp

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.

Accordion

Cheshire Rail Trail (Cheshire Branch Rail Trail)

We found the Trail notTrail not as described

October, 2023 by luvaneezer

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

Ashuelot Recreational Rail Trail

Still a lovely ride in spite of washouts

September, 2023 by nanlovell77

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.

Monadnock Recreational Rail Trail

Pleasantly Surprised

September, 2023 by fyredown

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!

Hillsborough Recreational Rail Trail

Bennington to Deering - compared with Jaffrey to Rindge

September, 2023 by fyredown

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!!!

Ashuwillticook Rail Trail

Good scenic ride

September, 2023 by richmedcraft

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.

Monadnock Recreational Rail Trail

not great conditions

September, 2023 by emilyahagan

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.

Monadnock Recreational Rail Trail

Nice trail, kept in good condition. Tree lined with lots of shade perfect for a summer day

September, 2023 by bplatt1

Nice trail, kept in good condition. Tree lined with lots of shade perfect for a summer day

Ashuwillticook Rail Trail

great trail

September, 2023 by dpwrztjhrw

Asphalt smooth and trail is terrific. Easy, flat trail with some water views passing Silver Lake/Pittsfield.

Ashuelot Recreational Rail Trail

South from Keene

August, 2023 by frankieoengine

A nice 5 miles to a huge wash out shutting down the trail. We bypassed the closure using the road for 1/2 mi. Only to find another sign saying trail closed. Turned around , do not plan on going more than 5 mi from Keene! Frankie

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Accordion

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