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 Ashuelot Recreational Rail Trail and Ashburnham Rail Trail . With more than 50 trails covering 440 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

Great Trail

October, 2026 by pokeystache

We rode from Pittsfield to Adams and back. Very nice trail. 50% shaded. Ate lunch at AJ‘s at Adams. Nice restaurant in an old train depot. Limited parking at the beginning in Pittsfield. Start your ride at the next parking area to the north. Lots of lakes and rivers running next to the trail. Asphalt the entire length of the trail.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

The good: it’s being paved. The bad: signage through Keene

October, 2026 by pammer1959_tl

We hoped to do the entire trail by parking in the middle just south of Keene. The signage going through town was minimal and included being on the road quite a bit. The south side noted “road closed” because it’s being paved, but the road dead ended after 2 miles.

Disappointed is an understatement.

Ashuwillticook Rail Trail

We rode the whole trail. It's smooth, scenic, and frequently bathrooms. The leaves are turning, such a beautiful trail. A must ride. It should be a Hall of Fame trail.

September, 2026 by sicnj2al

We rode the whole trail. It's smooth, scenic, and frequently bathrooms. The leaves are turning, such a beautiful trail. A must ride. It should be a Hall of Fame trail.

Accordion

Twin Cities Rail Trail

A few too many crossings at the Leominster end, but its a fine trail. Last quarter mile or so on the Fitchburg end isnt so much a trail as it is street riding.

September, 2026 by cedwardpierce923

A few too many crossings at the Leominster end, but its a fine trail. Last quarter mile or so on the Fitchburg end isnt so much a trail as it is street riding.

Ashuwillticook Rail Trail

Top Notch Trail

August, 2026 by trylondm

Biked end to end on a beautiful summer day. An absolutely beautiful paved trail with lots of water features to see - lakes to the south, river further north, and views of the mountains. Nice trailside pub in Adams and other eateries, including ice cream. Well-loved, with lots of walkers and skaters, as well as riders. Benches and picnic tables aplenty. One of the best trails I've had the privilege to ride. The only way it could possibly be better is if it was longer.

Correction to someone else's review: trail goes gently downhill south to north (not north to south) from Cheshire to Adams.

Catamount Trail - Sections 1 and 2

Catamount Trail Section 2

August, 2026 by awrootbeer

If you are a dedicated mountain biker than this would be a 5 star. Don't do this trail if you don't have a mountain bike or those fat tires. I was on a mountain bike, and my son had a regular bike. The beginning of the trail is easy and lovely. Once you connect with the trail (beautiful water views) the trail becomes mostly rock with some sand. Passed 1.8 miles the trail is impassable with our bikes. Somehow we made it out and back without falls or bike damage. I have biked other ski trails that were more compacted sand and dirt with some rock. This is not that kind of trail.

Ashuwillticook Rail Trail

Well maintained trail with great views

August, 2026 by sebastianmhill

Awesome trail. Smooth surface and great views. Also lots of different places you can join the trail. We started a little further north to skip the more industrial part of the trail.

Mass Central Rail Trail

Hadley to EastHampton- Norwottuck Rail Trail

August, 2026 by jlwinetrout

Beautiful 1st ride on the Norwottuck Rail Trail. We parked at the Marshalls in Hadley (trail starts right behind the building) and road a little over 10 miles into EastHampton and back. It was a very easy ride (my 1st ride of this length) on asphalt.

Ashuelot Recreational Rail Trail

Rough ride

July, 2026 by mroschella

Trail lacked any evidence of maintenance. Rode from Hinsdale to Winchester.

Manhan Rail Trail

Difficult to find the trailhead from Northampton but once you do....

July, 2026 by janieo

The Northampton part, which is reallly the NORWATTUCK RAIL TRAIL is really 2 stars bc it's so confusing. Needs fundraising and signage. But the rest, Manhan Rail Trail, is really nice. 5 stars. We took photos to illustrate but I unfortunately deleted them by accident.

We had stayed at the Hotel Northampton & nobody could tell us for certain how to find the trail other than to mention the railroad tracks. We found a paved path by the tracks & headed left. We passed a stone that said <- BOS/NHV --> and that's all. (Couldn't imagine how Boston could be to the left or straight ahead.) Within about 20 minutes, that path ended by some really rundown stores. On an aerial Google map, it reads as NORWATTUCK RAIL TRAIL (& shows it as a hiking &rail trail on the east side of the railroad tracks) but there is no signage anywhere to guide you. So when we got to the end, we turned around & headed in the other direction (south). THIS NORWSTTUCK TRAIL definitely needs some help. (Or maybe some day to be extended.)

Back to where we started out & this time heading in the other direction the trail actually becomes nice & very well marked. It seems to become the NEWHAVEN AND NORTH CANAL RAIL TRAIL (BUT there are no signs to this effect).

Where you meet the MANHAN RAIL TRAIL the signage is very clear, even as you are going through a village center or crossing a street or road, & the trail is very nice. You're following the reservoir & get some nice riding in.

We just kept going until we reached Easthampton. There you can even pick up trail maps! Ride on, and by the Municipal Bldg there's a nice park & large pond where you can see Mt. Tom behind it. Lovely, relaxing, scenic.

Then the ride back to Northampton but this time we knew the trail well & just enjoyed it.

North of Ferry St., at Lower Mill Pond, the Manhan Trail branches off and follows the river, eventually reaching the Connecticut River & Mt. Tom State Reservation. Should be a lovely ride! (You can also turn off here when you're riding south from Northampton.

Harrisville and Hancock Rail Trails

Not for everyone!

July, 2026 by ktrenaud

2.5 stars. Entered the trail a the far western end on Hancock Rd. near Skatutakee Lake. Biked eastward for several miles. Mixed surface (dirt, cinder, sand & forest floor). This trail is rough and best suited for fat-tire or full-suspension mountain bikes. You could do it with a gravel bike but be ready for a very bumpy ride. Partially buried track ties and roots cover roughly over a 3rd of this segment of the trail. The swamps and brook are absolutely beautiful. There are a few benches for a peaceful stop. The trail has a gentle decline most of the way so be prepared for the uphill on the return trip. Mostly shaded so sunscreen isn't needed but bug spray might be a good idea if stopping for prolonged periods. The bridges are beautiful & well maintained. The signage is discreet & informative. This is a wonderful all season trail that I plan to return to in foliage season. It has a lot of potential but in its current condition it has a LONG way to go to become a destination that will attract tourists & generate $$$ for the local economy.

Squannacook River Rail Trail

nice shorter ride

July, 2026 by slasalle76

Pleasant ride on this crushed stone surface, using my hybrid. Very short section that still has rails and ties and requests that bikes go around on the sidewalk, but easily joins back up to the actual trail after about 100 yards. The eastern end terminates in the Squannacook wildlife management area, with walking trails to follow down toward the river. If you are looking for a nice short ride that's under 10 miles total, this is a good one to choose. Stop for a bite at the local diner in Townsend center, or an ice cream.

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Accordion

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