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Greenfield, MA Walking Trails and Maps

963 Reviews

Looking for the best Walking trails around Greenfield?

Find the top rated walking trails in Greenfield, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.

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Length
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50 Results
Activities
Length
Surfaces
Type

Ashuwillticook Rail Trail
13.9 mi
State: MA
Asphalt

Blackstone River Greenway
31.6 mi
State: MA, RI
Asphalt, Boardwalk, Crushed Stone, Dirt

Bloomfield Greenway Multi-Use Trail
1.8 mi
State: CT
Asphalt

Bridge of Flowers
0.1 mi
State: MA
Concrete

Canalside Rail Trail
3.6 mi
State: MA
Asphalt

Columbia Greenway Rail Trail
3.1 mi
State: MA
Asphalt

Farmington Canal Heritage Trail
49.1 mi
State: CT
Asphalt

Grand Trunk Trail
6.9 mi
State: MA
Crushed Stone, Dirt, Gravel

Jonathan Daniels Trail
0.9 mi
State: NH
Crushed Stone

Keene Industrial Heritage Trail

1 mi
State: NH
Asphalt

Manhan Rail Trail
9.5 mi
State: MA
Asphalt

Mass Central Rail Trail
64 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Monadnock Recreational Rail Trail
7.5 mi
State: NH
Asphalt, Gravel

Quinebaug Valley Rail Trail
5.7 mi
State: MA
Ballast, Cinder, Dirt, Grass

Redstone Rail Trail
1.4 mi
State: MA
Asphalt

South Spencer Rail Trail
1.62 mi
State: MA
Crushed Stone

Southwick Rail Trail
6.5 mi
State: MA
Asphalt

West River Trail (Windham County)
16.1 mi
State: VT
Asphalt, Dirt, Gravel, Sand

Westville Lake Community Trail
0.7 mi
State: MA
Crushed Stone

Ashburnham Rail Trail
1.3 mi
State: MA
Dirt, Gravel
Accordion

Ashuelot Recreational Rail Trail
21.4 mi
State: NH
Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Cheshire Rail Trail (Cheshire Branch Rail Trail)
42.4 mi
State: NH
Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Common Pathway
5.5 mi
State: NH
Asphalt, Crushed Stone

Connecticut Riverwalk and Bikeway
7.8 mi
State: MA
Asphalt

Fort Hill Recreational Rail Trail
7 mi
State: NH
Ballast, Cinder, Dirt, Gravel, Sand

Harrisville and Hancock Rail Trails
6.1 mi
State: NH
Dirt

Hoosic River Greenway
2.5 mi
State: NY
Gravel

Lye Brook Falls Trail
2.2 mi
State: VT
Gravel

Mason Railroad Trail
6.7 mi
State: NH
Ballast, Gravel, Sand

North Central Pathway
11.2 mi
State: MA
Asphalt

Old Railroad Trail (NH)
2.7 mi
State: NH
Dirt

Potanipo Rail Trail (NH)
2.7 mi
State: NH
Crushed Stone, Gravel

Rocky Hill Trail

0.9 mi
State: MA
Asphalt

Squannacook River Rail Trail
3.7 mi
State: MA
Crushed Stone

Toonerville Rail-Trail
3.2 mi
State: VT
Asphalt

Twin Cities Rail Trail
4 mi
State: MA
Asphalt

Windsor Locks Canal State Park Trail
5.4 mi
State: CT
Asphalt

Brookline Rail Trail
4.5 mi
State: NH
Crushed Stone, Gravel

Chicopee River Canal Rail Trail
0.21 mi
State: MA
Asphalt

Corkscrew Rail Trail
3.8 mi
State: NY
Dirt

Granite Town Rail-Trail
3 mi
State: NH
Ballast, Cinder, Dirt, Grass, Gravel, Sand

Hillsborough Recreational Rail Trail
7.8 mi
State: NH
Crushed Stone, Dirt

Hoot, Toot and Whistle Trail & Riverwalk
2.3 mi
State: VT
Dirt

Valley Trail
9.1 mi
State: VT
Asphalt, Dirt, Gravel

Ware River Rail-Trail
15 mi
State: MA
Ballast, Dirt, Grass, Gravel

Appel Way Trail
1.3 mi
State: NH
Asphalt

Bennington Rail Trail
1.65 mi
State: VT
Asphalt, Crushed Stone, Gravel

Catamount Trail - Sections 1 and 2
18.1 mi
State: VT
Dirt

East Branch Trail (VT)
0.5 mi
State: VT
Gravel

Potanipo Rail Trail
3.4 mi
State: MA, NH
Crushed Stone, Gravel
Trail Image Trail Name States Length Surface Rating
Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along a 13.7-mile paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through the Hoosic...
 MA 13.9 mi Asphalt
Throughout history, the Blackstone River has been an important waterway, from its use by American Indians who fished its once-abundant salmon to its role as a major artery for the transportation of...
 MA, RI 31.6 mi Asphalt, Boardwalk, Crushed Stone, Dirt
The Bloomfield Greenway Multi-Use Trail currently runs 1.8 miles between Bloomfield and village of Tariffville in the Town of Simsbury. The paved rail-trail passes through woods and fields with...
 CT 1.8 mi Asphalt
The Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...
 MA 0.1 mi Concrete
The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...
 MA 3.6 mi Asphalt
The Columbia Greenway Rail Trail offers just over 3 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. About the Route The rail-trail runs between the Westfield...
 MA 3.1 mi Asphalt
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
 CT 49.1 mi Asphalt
The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. There are two longer sections of trail, in...
 MA 6.9 mi Crushed Stone, Dirt, Gravel
Jonathan Daniels Trail travels the length of Ashuelot River Park through Keene. Along the stone-dust trail, you can enjoy the park’s beautiful natural backdrop and flower garden. The trail was named...
 NH 0.9 mi Crushed Stone
The Keene Industrial Trail links the county's Cheshire Rail-Trail in the city of Keene. The paved path is a 1-mile segment through downtown Keene, which passes among some of the city's old mill...
 NH 1 mi Asphalt
The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
 MA 9.5 mi Asphalt
The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail trail. The Mass Central Rail Trail runs for 64 miles between...
 MA 64 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
The Monadnock Recreational Rail Trail is a great example of a repurposed rail route that provides safe commuting opportunities while also allowing trail users to escape into forest environments for...
 NH 7.5 mi Asphalt, Gravel
The Quinebaug Valley Rail Trail runs on the corridor once occupied by the Southbridge & Blackstone line of the Providence & Worcester Railroad, transforming a corridor once designed to link rural...
 MA 5.7 mi Ballast, Cinder, Dirt, Grass
The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
 MA 1.4 mi Asphalt
The South Spencer Rail Trail runs for less than 2 miles from downtown Spencer to an area south of town near Spencer State Forest. The path, which is also known as the Depot Trail, occupies a former...
 MA 1.62 mi Crushed Stone
The Southwick Rail Trail extends for 6.5 miles between the Westfield town line south and the Massachusetts–Connecticut state line. About the Route Along the way, the Southwick Rail Trail travels...
 MA 6.5 mi Asphalt
The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...
 VT 16.1 mi Asphalt, Dirt, Gravel, Sand
The Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
 MA 0.7 mi Crushed Stone
More than a mile of the Ashburnham Rail Trail opened in 2015 from a point just south of Ashburnham's center to Turnpike Road. The rustic route, planned to be paved in the future, offers a...
 MA 1.3 mi Dirt, Gravel
Accordion
Closure Notice: Due to flooding, the Ashuelot Recreational Rail Trail is closed from Pine Street to Sawyer's Crossing Road in Swanzey. Please see NH State Parks for more up-to-date information. The...
 NH 21.4 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
The Cheshire Rail Trail connects Fitzwilliam, Troy, Keene, Westmoreland and Walpole. The 42.4-mile trail has a mostly gravel and dirt surface. The rail-trail plays host to a variety of uses,...
 NH 42.4 mi Asphalt, Ballast, Cinder, Dirt, Gravel, Sand
The Common Pathway travels 5.5 miles from the outskirts of Peterborough south to downtown’s Noone Falls area, paralleling US 202 and the Contoocook River for most of its journey. The small town of...
 NH 5.5 mi Asphalt, Crushed Stone
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
 MA 7.8 mi Asphalt
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
 NH 7 mi Ballast, Cinder, Dirt, Gravel, Sand
Harrisville and Hancock Rail Trails run for 6 miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris Center...
 NH 6.1 mi Dirt
The Hoosic River Greenway spans 2.5 miles along the river’s east bank through the Village of Hoosick Falls. The gravel pathway follows the former route of the Boston Hoosac Tunnel & Western Railway,...
 NY 2.5 mi Gravel
The heavily wooded Lye Brook Falls Trail runs for 2 miles through the Lye Brook Wilderness of the Green Mountain National Forest near Manchester. The blue-blazed hiking trail follows the bed of a...
 VT 2.2 mi Gravel
The Mason Railroad Trail runs for nearly 7 miles from near the New Hampshire–Massachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...
 NH 6.7 mi Ballast, Gravel, Sand
The North Central Pathway is envisioned as a trail network connecting points of interest through and between Winchendon and Gardner. Several completed sections of trail make for a lovely ride or walk...
 MA 11.2 mi Asphalt
The Old Railroad, as its name suggests, is a multi-use trail that occupies a former Boston & Maine Railroad corridor. The trail picks up at the northern trailhead of the Common Pathway, a paved...
 NH 2.7 mi Dirt
Following the Nissitissit River through the woods, the Potanipo Rail Trail offers beautiful river views and launch sites for canoes or kayaks. Composed of two segments, the multi-use path is roughly...
 NH 2.7 mi Crushed Stone, Gravel
The Rocky Hill Trail weaves through the tranquil greenery of the Burts Bog Greenway Conservation Area in Northampton, Hampshire County. The 121-acre peat bog is an ecologically sensitive site that's...
 MA 0.9 mi Asphalt
The Squannacook River Rail Trail is 3.7 miles long, from Depot St in the center of Townsend, MA, to the Bertozzi Wildlife Management Area in Groton, MA. The trail occupies the Greenville Branch of the...
 MA 3.7 mi Crushed Stone
The Toonerville Rail-Trail shadows the Black River for most of its 3.2-mile length in eastern Springfield to the border with New Hampshire across the Connecticut River. The route originally carried an...
 VT 3.2 mi Asphalt
The Twin Cities Rail Trail is a 4-mile multi-use trail that connects downtown Fitchburg and downtown Leominster, offering a variety of recreational opportunities and providing an alternative...
 MA 4 mi Asphalt
Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor...
 CT 5.4 mi Asphalt
The Brookline Rail Trail winds through the New Hampshire woods and passes by several small bodies of water, including the Potanipo Pond. The rail-trail has two segments, known as the Brookline Rail...
 NH 4.5 mi Crushed Stone, Gravel
The Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
 MA 0.21 mi Asphalt
The first section of the Corkscrew Rail Trail opened in June 2015. It begins at Knapp Road in Stephentown and heads south under a shady tree canopy towards New Lebanon, near the New York/Massachusetts...
 NY 3.8 mi Dirt
The Granite Town Rail-Trail runs for 3 miles in Milford, New Hampshire. Portions of the route are unpaved and surfaced with sand, gravel, and/or dirt, while short concrete sections can be found along...
 NH 3 mi Ballast, Cinder, Dirt, Grass, Gravel, Sand
Hillsborough Recreational Rail Trail connects three communities in south-central New Hampshire: Hillsborough, Deering, and Bennington. The unpaved trail winds along the Contoocook River through rural...
 NH 7.8 mi Crushed Stone, Dirt
Although short, the Hoot, Toot and Whistle Trail provides an enjoyable journey through peaceful woodlands on Wilmington's west end. As you might guess, the rail-trail gets its name from the former...
 VT 2.3 mi Dirt
The scenic Valley Trail spans 9 miles connecting Dover and Wilmington in southern Vermont along the Green Mountain National Forest. It provides a critical off-road pathway for bypassing State Route...
 VT 9.1 mi Asphalt, Dirt, Gravel
The Ware River Rail-Trail is an unpaved 15-mile rail-trail that stretches between Barre and Baldwinville, running through Hubbardston and Templeton along the way.  Following along the Burnshirt...
 MA 15 mi Ballast, Dirt, Grass, Gravel
Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection between Wheelock Park on the trail's west end and Ashuelot River...
 NH 1.3 mi Asphalt
Running between downtown Bennington and the Northside Drive neighborhoods, the Bennington Rail Trail provides new opportunities for both recreation and active transportation. Following a former...
 VT 1.65 mi Asphalt, Crushed Stone, Gravel
The Catamount Trail offers 300 miles of backcountry skiing stretching across Vermont, from the Readsboro on the Massachusetts border, to North Troy near Canada. The trails are popular for winter...
 VT 18.1 mi Dirt
The East Branch Trail is a 0.5-mile ungroomed, backcountry pathway built on a former logging railroad bed in southern Vermont's Windham County. The remote, heavily wooded trail lies just north of the...
 VT 0.5 mi Gravel
The Potanipo Rail Trail is composed of three segments across New Hampshire and Massachusetts. Running through the woods along a former a rail corridor, the trail parallels the Nissitissit River for a...
 MA, NH 3.4 mi Crushed Stone, Gravel

Recent Trail Reviews

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.

read more …

Ashuelot Recreational Rail Trail

Rough ride

July, 2026 by mroschella

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

read more …

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.

read more …
Accordion

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.

read more …

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.

read more …

Ashburnham Rail Trail

Short but scenic

June, 2026 by bhaalck

0.8 miles of this trail now consists of crushed gravel

read more …

Hoosic River Greenway

Parked in middle waked each way, nice leisurely walk.

June, 2026 by tchioc88_tl

Parked in middle waked each way, nice leisurely walk.

read more …

Farmington Canal Heritage Trail

Rode Simsbury down to Plainville. Simsbury to Avon was full of tree root bumps, and lots of branches & trail debris. It's almost as if Simsbury wants to keep cyclists out. ¿ However, Avon and Farmington were great rides, as was Plainville.

June, 2026 by taccuosti

Rode Simsbury down to Plainville. Simsbury to Avon was full of tree root bumps, and lots of branches & trail debris. It's almost as if Simsbury wants to keep cyclists out. ¿ However, Avon and Farmington were great rides, as was Plainville.

read more …

South Spencer Rail Trail

Quite and Peaceful

May, 2026 by don.gerardi

Lot's of stops along the way to enjoy the sites. It's a very well maintained small trail

read more …

Ashuelot Recreational Rail Trail

pleasant ride

May, 2026 by slasalle76

I'd ridden this trail a couple years ago, doing it in small sections, and had found it to be a nice ride with a decent surface, quite reasonable for my older hybrid. I only did about 6 miles today, from Keene southward before turning back, and those couple of detours noted in another review are still in place - taking you out onto the road for short stretches likely to avoid power line work being done.

read more …

Farmington Canal Heritage Trail

Terrible Shape

May, 2026 by dave36

Rode from Avon, CT to Westfield, MA. Mass section in great shape. CT section is awful. Pavement is split, constant 'ka-thunk', pot holes not marked, just horrendous condition. Where is the CT DOT and our tax dollars? Stay away.

read more …

South Spencer Rail Trail

Quite and Peaceful

May, 2026 by don.gerardi

Lot's of stops along the way to enjoy the sites. It's a very well maintained small trail

read more …
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Explore by Activity

ATV
Bike
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Running
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