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 385 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

John & Lisa

June, 2023 by handyj418

June 2023
This trail is second to none! Rode from Lanesboro to Adams-- flat, clean great scenery. Many turtles, water birds, and spotted a deer. Considering a return in the fall as I am sure the color is amazing.

Ashuwillticook Rail Trail

Great trail in MA!

June, 2023 by steve.schwinn

Road the trail last week end-to-end as an out and back from the great southern trailhead parking area on Crane Avenue (bathroom). Trail is in excellent condition and a great ride.

Farmington Canal Heritage Trail

Combination trail ride into MA

May, 2023 by steve.schwinn

Road part of this trail as an out and back in conjunction with the Southwick RT and the Columbia Greenway RT from Avon, CT, to Westfield, MA, an approximately 50 mile round trip (25 on the Farmington Canal Trail).
The trail is in very good condition. The transition to the Southwick Trail at the CT/MA border (with no road crossing) is seamless.
Road crossings decrease as you head north and are well marked with push-button warning signals to alert traffic.
Half Mile Falls Park at the north end of the Columbia Trail in Westfield is definitely worth a stop!

Accordion

Southwick Rail Trail

Great trail with seamless trail connections at both ends!

May, 2023 by steve.schwinn

Road this trail as an out and back in conjunction with the Farmington Canal Heritage Trail and the Columbia Greenway RT from Avon, CT, to Westfield, MA, an approximately 50 mile round trip.
The trail is in excellent condition. The transitions to the Farmington Canal Trail at the CT/MA border (with no road crossing) and to the Columbia Greenway RT on the north are seamless.
The mileage markers are great!
Half Mile Falls Park at the north end of the Columbia Trail is definitely worth a stop!

Columbia Greenway Rail Trail

Trail closure

May, 2023 by steve.schwinn

Road part this trail as an out and back in conjunction with the Southwick RT and the Columbia Greenway RT from Avon, CT, to Westfield, MA, an approximately 50 mile round trip.
This trail should be a 5 but it is closed at Main Street in Westfield with no information on when it will reopen or detours.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Beautiful section in terms of scenery and access to lakes and ponds. The surface can be challenging. Today, with fairly dry conditions, it could be negotiated with hybrid bikes.

May, 2023 by earthman58

Beautiful section in terms of scenery and access to lakes and ponds. The surface can be challenging. Today, with fairly dry conditions, it could be negotiated with hybrid bikes.

Corkscrew Rail Trail

a very straight section

March, 2023 by bob.stijne

There are no curves or bends in this section. Just a straight line. There is a dirt track in the middle. For the kids there are signs with questions which is nice

Southwick Rail Trail

please beware

March, 2023 by jillm56

It’s a beautiful trail. BUT, please beware of the yellow post they have installed at all the road crossings to keep motor vehicles off the trail. As I was crossing the road at one of the crossings, as I came back onto the trail my handlebar caught the post and sandwiched me in my bike and the bike and I went down hard. I ended up fracturing my back. So please be careful on this trail through Southwick.

Mass Central Rail Trail

Weston part not the best for rollerblading

February, 2023 by 7q2vdb7mbx

The pavement is decent, but there’s no marked center line. Biggest complaint is that the trail primarily goes downhill as you go east, and primarily uphill as you go west, so you’re going to hate one direction or the other. Decent views. Poor road-to-trail transitions with broken up pavement and sand which is a nightmare for in-line skates. Much prefer the Cochituate rail trail

Windsor Locks Canal State Park Trail

I do my run here a few times a month, It is so beautiful I really like it. It is so green and right next to the CT River the air is so clean. It's good for a long run where you can get up to 10 miles and it's a well maintained trail.

February, 2023 by yikertam

I do my run here a few times a month, It is so beautiful I really like it. It is so green and right next to the CT River the air is so clean. It's good for a long run where you can get up to 10 miles and it's a well maintained trail.

Twin Cities Rail Trail

walking.

February, 2023 by caddydvr

Love this rail trail !! Nice easy path , street crossings are easy to get thru. Great job by both cities.

Ware River Rail-Trail

Great if you like exploring, like I do.

January, 2023 by alan113

Rode (7/22) from Winchendon to Baldwinville, and then (skipping the part bisected by Rt. 2) from from Rt. 101 in Templeton to Route 122 in Smithville on the Barre/Oakham line. Lots of wet and rutty sections north of Balwinville but still fun (some walking with 1.5" tires). Some sandy section in the southern piece but still fun. It's slow going of course. Didn't pass a single extra person. Good roadside fried food at Lee's in Baldwinville (it's been there for at least 70 years!)

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Accordion

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