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 419 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

Mass Central Rail Trail

Ware to Gilbertville and Gilbertville to Wheelwright

November, 2024 by arno911

Rode the two sections of this beautiful trail today. From the parking spot in the middle of the Ware trail towards Gilbertville is a nice ride along the river. But a short one. Opposite the old factory the trail suddenly ends and there are handwritten signs "Stop, Don´t go further, Private property..." It would only take a few yards to reach the next road to travel on towards Gilbertville. No chance. Shame on you, property owners! (The trailmap shows a way through, but that might be an error?)

Okay, same way back and on to Route 32 past Gilbertville, where the next trailhead is waiting;-)
Smooth surface, well maintained and even good for kids bikes and flat all the way to Wheelwright. 3 nice old bridges. This is one is fully recommended! Absolutely worth it.

Blackstone River Greenway

Wonderful trail

November, 2024 by walkinator007

This is my favorite trail in the state, very scenic along the river. best part is from woonsocket to lincoln. Some parts of this trail through the city are poorly marked and you need to share the road with cars.

Common Pathway

Nice trail ride with a great finishing destination

November, 2024 by georgerisktaker

The Common Pathway is also called the Peterborough RT. This RT adjoins the Old Railroad Trail and is about 5 miles north of Monadnock RT (we did all 3 trails the same day). The trail is mostly crushed stone but some asphalt as well as road ride. Some rough spots but no issue. Started at Trailhead for Old Railroad Trail and headed toward Peterborough. It is a nice town with several good eating and drinking places. Good trail and the Contoocook River runs along most of the trail. We did not do the trail south of Peterborough as it went from town, along 202 (traffic at 50+ mph) and was not reviewed as being an interesting ride.

Accordion

Old Railroad Trail

Rustic and bumpy deep woods ride (good feel)

November, 2024 by georgerisktaker

e-Bike with 2" tires. The trail adjoins Peterborough (Common Path) RT. Rough trail with roots and rocks, so speeds above 10 are impossible to maintain. On a positive note, you really feel like you are in the woods. We were able to go slightly longer than the miles posted. A tiring short ride, but doable. Wife hated it, as too bumpy. Recommendation: ride Peterborough (Common Path) first as it is much easier.

Monadnock Recreational Rail Trail

Monadnock Recreational Rail Trail

November, 2024 by georgerisktaker

Biked with e-bikes 2" tires. From the north going south (American Legion Baseball Field). Mostly crushed stone trail. Feels like a rail trail - level and wide. Only one rough area (RR ties and rocks for about 10 yds). The water on the left of the trail looked like it was drying up (no smell) and there was at least one nice lake (average views). Part of the trail runs along the highway. Only rode 5 miles as we didn't go much south of 202 (exceedingly difficult crossing at rush hour - be careful). Some of the reviews of the area south of where we rode indicate more difficult terain.

Brookline Rail Trail

Brookline Rail Trail

November, 2024 by georgerisktaker

Rustic dirt trail that is like Granite Town RT (is a little easier) as it is dirt and connects with it.  We quit at the Teva section as signs were posted "Private Property," even though camp was not in session. 

Ashuwillticook Rail Trail

Mid-Fall Ride

October, 2024 by willipar

Rode the full trail on a glorious October Saturday. the views were spectacular, peppered with fiery fall leaves. The trail is in incredibly good condition over the whole length. Such a lovely ride.

Squannacook River Rail Trail

nice path for leisurely ride

October, 2024 by sweetcfortin

Super well Maintained gravel. Nice views in south side of trail, but the view on northern side is kind of industrial. Trees are gorgeous in the fall. Hope they extend this soon!

Granite Town Rail-Trail

Rustic and difficult in parts for bikes other than mountain bikes

October, 2024 by georgerisktaker

We did this trail with e-bikes with 2.1" tires. This all-dirt trail is very rustic and narrow in parts. From the north, after .5 miles you will start to feel the presence of tree roots which at times are very dense - so dense that they are difficult to ride over at any speed. From about .8 to 1.2 miles the trail goes up and down a hill which is all rocks and anything other than a mountain bike will need to be walked.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

hazardous obstacle course

October, 2024 by bikerdoc

My wife and I are both injured(fortunately not serious) after both of us thrown off our bikes simultaneously on a small poorly surfaced wooden bridge just north of Keene NH. The wooden boards were uneven and some rotted causing our bikes to wedge in a step-off causing us both to fall off our bikes. The trail had several road crossings just outside of the town of Keene which are very dangerous. There are tiny stop sign markings on the trail and no large or blinking light warnings on the crossing roads which have poor visibility in both directions due to curving of the road. I would not recommend this trail for transient travelers trying a new RT on vacation. This is for locals only who know the trail well in my opinion.

Canalside Rail Trail

Trail Closed

October, 2024 by joerone_tl

Part of this trail is closed, my wife and I got about 2 miles or so in and there was a detour sign for the trail and we could not find where it picked up again. Road on the streets for a bit and then headed back to the truck, got about 5 miles in on the ride so not a total loss

Fort Hill Recreational Rail Trail

great trail

September, 2024 by leslie.sherman316

We did this trail today. It is quite bumpy but the scenery more than makes up for that. It goes through beautiful forests with frequent views of the Connecticut River. Don’t pass it up if you are in the area.

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Accordion

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